The thing about cycling on the road for transport -- whether that means commuting to work, to the store, or to go hang out, is that you have to plan a bit. You can't carry everything with you -- even if you didn't mind looking like a Sherpa loaded for K2 you'd still have trouble getting between cars with that much gear on your back or bike. Not to fret, though... after a while you quickly learn what you need or don't and pack accordingly.
BIKE
Number one: a bike. There are two main types; mountain bike and road bike. Within these however the differences are as vast as between them. There are rigid mountain bikes, without suspension -- with harder, smoother tires, and perhaps a change of gearing, these can make excellent road machines for commuting or transportation. Within in road bikes -- well, do you want a traditional road bike or something with flat bars? Some hybrids -- road bike size wheels married to an upright riding position -- can be as fast and sport-oriented as some entry level road bikes with drop or curved bars. Sport hybrid or performance hybrid, in fact, is a relatively new but growing category or bicycle.
MOUNTAIN BIKE:
Rigid
Front suspension
Full suspension
ROAD BIKE:
Drop bar (traditional) road bike
Touring bike
Cyclocross bike
Hybrid
Performance hybrid
Track bike
The main difference here is wheel size. Mountainbikes typically have 26" rims, road bikes have bigger rims, 700 (metric) or for older models, 27", and narrower tires. Hybrids you will note are in the road bike catagory, but primarily because of wheel size. Mountainbikes: For transportation unless you will find yourself riding down stairs or engaged in fantastic car chases over rough terrain, you probably don't need shocks or suspension, so if you pick a mountainbiek go with a basic (rigid) model. Or, if you want or happen to have a nicer model, remove the suspension fork and replace it with a stiff one with no shocks. This not only removes excess parts and prevents unneeded repairs thereto, but also cuts weight dramatically and will improve the handling of your mountainbike on the street or even smooth dirt trails. How will you ride without shocks, you say? First the mountainbike is still plenty sturdy without them -- and so are you. People have been riding rigid bikes offroad for over a hudnred years... before "moutnain bikes" existed!
Some people do use front or even full suspension mountain bikes for street use, with slick or semi-slick tires but it is often overkill and the shocks simply add extra weight and an extra piece of equipment to maintain. Also on hard flat surfaces suspension can be an inconvenience causing the bike to "bob" up and down and rob you of energy as well as possibly impair your control; a hard application of the brakes, for example, if a car cuts you off (to use just one commonplace instance) can cause the bike to sag under you. This is especially true of entry level or basic suspension which is often not adjustable. If you are going to ride a mountain bike with suspension on the roadways a suspension that allows you to "lock out" its function is the lesser evil. Examples include Cannondale’s Headshock and the forks on some Gary Fisher mountain bikes.
If you pick a mountainbike, plan on modifying it, beyond the fork, if it's suspended: Also put on slick or semi-slick tires, tired without big knobby tread and with higher pressure. This will make your bike roll more easily be decreasing rolling resistance. You may have to change the gearing. A slightly larger or smaller set of chainrings or rear cogs may be needed to adjust for road use. Keep in mind, although you can go as slow or fast as you like, within reason and safety, you are safer moving as close to traffic speed as you can compared to poking along at a walking pace on the roadside. This is especially true if you are going to be more fully interacting with traffic, making left turns, etc. A properly geared and set up bike, mountain or road, can accelerate from a stoplight across an intersection faster than the average car; up to 15 or 20 mph it can't be beat for going from zero to moving. But if your gearing is poorly chosen you could be stuck being a slowly moving target!
Frame material is also an issue. Steel does rust if not cared for constantly under some conditions but is less likely to be destroyed by dings and mishaps that can total an aluminum or carbon frame. Indeed, a dented steel frame can often be ridden home while an aluminum one could crack. This is a general statement of course and there are variations but steel also provides a more comfortable ride than many cheaper aluminum frames. With mountain bikes, steel is used typically on only the lower end and, paradoxically, very high end models, for different reasons; the low end rigid bikes are less technical and so they typically offer a basic model in this traditional material; with higher end bikes steel is seeing a resurgence but these can be expensive and do you really want to lock a $1,200 bicycle up outside a store while you go shopping?
Road bikes are an easier choice to make among them, because of the lack of suspension; the frames are all pretty much the same design except for materials used, i.e., steel, aluminum, carbon, or in some cases, a combination of two such as carbon and aluminum, such as in my Masi: Basically the differences are in ride position, gearing and brakes. A road bike will typically be offered with either 2 or 3 front gears, and the size of the gearing even there varies; there are compact doubles and standard doubles. A hybrid or performance hybrid typically offers a mountain bike style handlebar for a more upright position; 'cross bikes and touring bikes offer beefier, more heavy duty frames and cantilever or linear pull brakes; some even come with disc brakes, previously seen only on tandems or mountain bikes. A fixed gear or track bicycle is a single speed, typically using road size rims and tires that cannot coast. A track bike has racier geometry and handling as it is meant for racing around a banked track; however some entry level track bikes come with more road-style geometry as the manufacturers know they will be used on the road as well. A fixed gear offers less parts to maintain and a fine ride in many circumstances.
Contrary to popular belief it is indeed possible to go up hills on a fixed gear machine; however, since you only have one gear choosing the gearing for the bike involves a compromise, a gear that you can turn over from a stop in traffic and a gear that will allow you to move at traffic speed as well as climb hills when needed without busting a lung. 42/16 is a common middle of the road gearing combination; I personally prefer 43/17 which gives me a little more spin on hills.
Ultimately you have to decide what sort of ride position and quality you want. A mountain bike or hybrid gives a more upright position. But a full on dual suspension mountain bike will be as much overkill for doing errands around town as a full-on road racing bike like the carbon-aluminum Masi. As to the upright position of a mountain bike or hybrid, this is good for around town use and even for longer rides, inasmuch as it is more comfortable for your back for beginners and also provides good visibility for you and drivers to see you as well. In this way it is beneficial; if you don't mind the limited hand positions compared to drop bars or forward-pointing "bullhorns". However, flat or riser mountain bike bars are not as good for climbing, partly due to the lack of different hand positions, partly due to the difference in right position and weight distribution when a rider is standing on the pedals compared to a road bike, so if your route will take you on hills, consider that. Also into the wind... you can reduce the wind resistance inherent to mountain bike bars by using a lower stem, but they still aren't as efficient, by and large, as drop bars. Also even with slicks or street tires, a mountain bike will not be as fast as a road or track bike. It is simple physics.
On the other hand, mountain bike frames offer more clearance around the wheels, allowing much wider range of tire choices; in winter you can put on off-road or knobby tires for the snow, or keep a set of spare wheels with such tires. It is possible to use wider tires on cyclocross and touring bikes and some older road bikes of the "ten speed" era, but most modern road frames have tight frame clearances and will not fit wider tires. Mountain bikes may be heavier -- but also somewhat more durable. Are you going to have to hop curbs or ride through really bad potholes? You might not want a road bike; a cyclocross or mountain bike might be better. On the other hand, will you be traveling longer distances on open road? A mountain bike might be limiting...
Older hybrids are a nice compromise; newer models tend to be "comfort" oriented in the cokcpit, with a "sit-up-and-beg" ride position; older models often had similar geometry to mountainbikes or road or touring frames, allowing more efficient ride position. The flat bar of a hybrid is not going to be as efficient as a roadbiek over long distance at speed, but an older hybrid such as my lugged steel Schwin CrissCross can offer a nice compromise between road bike and mountainbike; the bigger wheels and narrower tires roll better and faster, but the bike fits tires with more tread for foul weather and has cantilever brakes like a mountainbike. It even has eyelets for mountaing a rack to the frame. With treaded tires of a moderate size -- 700x32 cyclocross tires, in this case -- it makes a decent commuter.
Newer, "performance hybrids" are a different new catagory; basically they are similar to road bikes except for the handlebars and, sometimes, brakes, which are still either cantis or v-brakes. Often they have racing, road style tires and other "performance" features such as integrated headsets and outboard bottom braket bearings; some even have carbon fiber forks. Like older hybrids, they allow a slightly more efficient agressive position compared to "comfort' hybrids, but the flat bar still divides them from the traditional road bike.
Another consideration is fender mounting. In the past, it was difficult to mount fenders on more "racier" road frames or track bikes. However, the advent of clip-on fenders that attach to the lower part of the seat post mean that practically any bike can be outfitted with a fender for moderate foul weather.
And any decent old road frome can usually fit fuller fenders of some sort, especially if it is a 27" frame running modern 700 rims which gives slightly more clearance as a result, such as this Ross fixed wheel commuter: 
When you choose your bike, what do want to do to it? It might behoove the rider of a mountain bike to change the gearing for the street; adding a larger chain ring to the front, say a 44 or 48 tooth ring, might make sense. Or, a rider may remove extra gears and simply run a single chain ring up front in conjunction with the gears in the back. Conversely, the rider of a road bike who uses it for around town use or even city use might feel it is over geared, and switch the standard 52 or 53 tooth "big ring" for something somewhat smaller like a 44 or 48. You can also change the gear cluster in the back, in the old days, a freewheel, now more likely than not a cassette, but this involves a little more technical knowledge; the chain rings on the other hand can be swapped out in five minutes using an allen wrench. One notation; the advent of modern highly specialized drive trains for bicycles means that what may work with one may not work with another. A bike that has six gears in the back will run a different width chain than one that has 10 gears in the back. However, it is easy enough to make sure the chain ring you are going to use will fit the chain on the bike.
My everyday ride for normal longer trips is a fixed gear road frame with aforementioned 43/17 gearing or a similar one with 42/17 gearing and full fenders when it's raining -- or a Fuji track fixed gear set up with 39/16 gearing. When I commute on a road bike it's usually a Trek 1000 I've reassembled with a 48/39 frotn chainring set instead of the stock 53/39, which is better for spinning around with a load or simply getting where one needs to go. Picking the right bike is important, but so is fit. Make sure the bike fits you; if it does not you will not be comfortable, could find it harder to control, and may injure yourself.
Keep in mind that basically, no matter what bicycle you select, you will have to do some degree of customization for fit at the least; often as you ride more you will customize the bike by swapping out additional parts to increase performance. This doesn’t necessarily mean speed-racer-like advancements in handling or top speed; “performance” is a sort of catch all term. To the utilitarian cyclist it includes not only making the bike faster, or more efficient, which would include making it easier to go fast, i.e., by reducing the rotating weight of your wheels, by, say, switching to lighter and stronger rims, or smoother-operating shifters, but also long term durability, ease of maintenance and use. In the bicycle world performance is too often associated with pure speed, but speed by itself is not particularly useful outside of a race or sport club environment. Example: having ten gears on your rear wheel instead of 6, 7, 8, or even nine gears, might make you faster; if you shell out a small fortune for the new eleven speed rear cluster that Campagnolo has debuted, it might even be better still, from a technological advancement standpoint. However, higher numbers or rear gears require somewhat specialized chains much narrower than on traditional six to eight speed rear gearing, and the chains in turn require more specialized tools and knowledge to work on. A six speed chain can be removed or replaced with a chain tool used to push out a pin from any link. The newer narrower chains require special master links and in some cases special tools. Also the more gears on the rear wheel the more sideways pull on the chain when in extreme gear combinations; example, a rider using the big gear in the front and the big gear in the bag will have the chain at a more acute angle on a ten speed rear gear setup than with six speeds. All of these things add up to maintenance considerations, not only in terms of when it’s time to clean or tune up the bike, but in terms of things that might go wrong on the road.
And, if you really want that speedy bike, keep in mind, cyclists were going fast long before gears became standard equipment on race bikes. In the Tour de France prior to WWII they were using double sided single speed hubs, with gearing such as 46/22 or 46/24 for climbs.
The bulk of the modifications you initially do to the bike will be in the contact or control areas; your handlebars, handlebar stem, seat or seat post, and pedals. These include not only switching parts, such as a 42 cm road handlebar for a 44, if you realize you want a wider one, or modifying parts, such as cutting half an inch off a pair of mountain bike handlebars to shorten them, but also simple adjustments, such as raising or lowering the handlebar stem or seat post, moving the seat fore and aft, or adjusting the angle. A lot of this will be done by the bike shop you purchase the bike in, if you get it new. They will often swap parts for the equivalent to adjust sizing issues within the range of body sizes for that size frame bike. Some bike shops also offer bike fit procedures where a professional suggests the modifications for you.
BAG
Number 2: A bag. A backpack, messenger bag, or mounted on a bike rack. Some way to carry your gear. Any decent messenger bag or backpack will do, as will a large seat bag or a bike rack and trunk bag or panniers. I normally use either a Chrome or Reload messenger bag for longer trips; for around town stuff I use a Tibmuk2. Since having shoulder surgery however I am using a smaller Chrome bag that has a split strap with their well-known "seatbelt buckle"; this allows me to put the bag on and off without lifting it over my head with my bum arm.
Whether you choose a backpack, messenger bag, or bike rack bag, keep in mind 3 things: durability, visibility, and water-resistance. You want a bag that won't self destruct after a month on the road. You also want a bag that, either on your back or the bike, won't block your ability to glance over your shoulder prior to changing lanes or turning etc. This is especially important with choosing a backpack. Lastly, you don't want your stuff getting soaked. Most panniers and messenger bags are waterproofed or resistant. Some cycling backpacks or messenger bag backpacks, like the Ortlieb or Chrome Dually, are also similarly constructed. Some regular backpacks some with rain covers. In a pinch, a regular backpack can be made more resistant to the rain and road splash by putting your stuff inside it into a waterproof rolltop stuff sack. Stuff sacks are made by companies like Sealline or Outdoor Research, and a lot of backpack companies make rain covers. A mid line between courier backpacks and a backpack from Wallmart is a sports pack of sometimes cycling spacific pack. Even a pack designed for hiking, of the right proportions, will work better than a cheaper made pack not designed for the long haul, and have more features, often including reflective logos or accents -- as well as places, like compresion straps, for savy riders to sew or tie on their own reflectors or lights. In my case I sometimes use a North face daypack, my favorite being the Recon because it's back mess pocket fits a road helmet fine. I removed the thick padding fromt he back so the bag woudl not be as wide, but this necessitated cutting the fabric and re-sewing the liner by hand. You may not want to try it. Even with the thick padding, however, the pack rides okay. Other comapnies that make outdoorsy or sporty packs better than your average bookbag, although still not purely for cycling, include Osprey and Deuter. Some companies, such as Detours, make backpacks specifically designed for cyclists. Note there are now several kinds of two strap backpack involved: courier-style ones with waterproof or resistant linings, regular deptarment store packs, and sports packs, plus bicycle specific packs. We have to also consider hydration packs. With the bladder removed the largest, such as the Camelback HAWG, make decent small sized backpacks, able to carry a change of clothes or a sizpack, if not much else. However, these devices are often a red herring. Any internet search of bicycle backpacks will turn up references to hydration packs. A hydration pack is not a backpack. This only underscores the derth or real options for cyclists lookng to carry their gear and get around by bike, on daily commutes or errands where all the needed gear won't fit in 3 elastic jersey pockets the way it does on a fast Sunday training ride. In this way the world of cycling backpacks is very small indeed, consisting of some made by cycling clothing brands (Pearl Izumi Velocitrak), mail order bicycle dealers (REI Novara commuter backpack) and small companies not likely to be stocked by ramdon sporting stores (such as the Detours bhiclyce backpacks). Please note again that unliek courier bags or packs, they usually do not have waterproof linings although many come with rain covers, virtually all can be fitted with them, and some have them built in or stowed in special pockets. In the bag: This is what I take -- A small pouch with a multi-tool, 15mm wrench (for bolted axels), tire levers, pump, and at least one spare tube. At least 2 bottles of water. Locks (at least 2: u lock and cable/padlock in the bag, or if I'm using my thick chain instead of the cable I sling it around my waist). Cell phone, wallet, lights, spare batteries, notebook, and a change of shirt if I'm going to work, and pants... It a minimum this is what I take. I use a medium to large sized Chrome courier bag, medium Timbuk2 bag (although it gets full at work when i put my helmet it) and sometiems a backpack, either a chrome messenger backpack or a North Face backpack.
LOCKS:
If someone really wants to steal your bike -- or your car, or your watch -- they will find a way to try. Might not succeed, but could easily damage it in the attempt. To this end you lock your bike not only to prevent theft, but to discourage the attempt in the first place. I would advise using several locks. A plain lightweight cable and padlock with is easy to carry and use is fine for your own neighborhood, if you live in a suburban area with low theft risk and will only be locking the bike momentarily, such as while running into a store for a cup of coffee. However, it is better to use several. A middle ground is using two forms of attachment but only one locking mechanism; use a u-lock and a cable. Lock the u-lock through the frame (and one of the wheels, if it will fit, and lock this so something immobile, like a railing or bike rack, if they have one). Then before you close it put the cable through both wheels and the frame and what you are locking the bike to. The u-lock not only locks itself but the cable. For locking your bike up for a longer time I'd suggest two or 3 locks. A u-lock and either a length of chain or a cable, with a separate padlock. Sometimes a third lock can be useful too. The idea is to make the thief think that it is more trouble than it is worth to try and steal your bike.
BELLS:
These are useful only if you are going to be pasing a lot of stationary pedestrians waiting to step in front of you (such as from a downtown curbside). However, they are absolutely useless for automobiles or even other bicycles. Wind noise can often make a shout unclear to another rider riding alongside you on a downhill; how then do yu expect a car driver to hear a bell inside his car with the windows closed? He can't.
MIRRORS:
Like bells, mirrors sound nice in concept but in practice are not that useful except as a psychological aid. Most cyclists can time overtaking cars by sound; also, in a pinch, you can look over your shoulder. Of course, the more uprigth your ride position the harder looking completely over your shoulder becomes; on a road bike or track bike, or even a mountainbike with fairly agressive posture, it is natural and hardly takes thought.
On a bike with clearly "upright" handlebars, a rider will find looking over his or her shoulder more difficult [as I discovered after putting raised riser bars on my mountainbike to use it after a shoulder operation since I was not supposed to extend my arm for the reach needed with a normal riding position until the shoulder had healed]. The result is it is more difficult and the motion is less natural. This makes it understandable why so many people are in love with mirrors; a lot of people commute on bikes with a pronounced upright riding position. However, since most problems are in front of you, not behind, and most accidents and close calls occur from other vehicles turning across your path, not traveling alongside, the usefulness of mirrors is marginal at best.
This isn't to downplay the danger of being struck from behind; such accidents do happen especially as more and more roads switch over to substandard lanes narrower than what has traditionally been deemed safe, in an effort to fit more lanes on each road, and drivers try to cram more and more SUVs and trucks into them. In fact, I myself have had close calls -- typically with passing SUVs or pickup trucks who are either ignorant of how far their huge side mirrors jut out, or don't care. However, most of the time a cyclist can tell by sound if such a vehicle is approaching -- and the eyes are better up front; in my time of riding I've had only one near miss by overtaking pickup truck, but half a dozen hits and near misses by drivers turning across my path. Indeed, the only time I was ever struck by a vehicle traveling in parallel direction of travel I was on foot, carrying the bike with flat tire!
People often say "you wouldn't drive your car without mirrors woudl you?" The comparison is apples and oranges, at best. In a car a driver is not capable of hearign the road as well or looking around -- although I and I'm sure some others do drive with their windows at least partially open most of the time, when I must use a car, so that I may hear the road better. As a result I have heard the tapping feet of runnign jaywalkers before they darted in front of my as the traffic light turned green and thereby avoided a crash. Rather than say you wouldn't drive your car without mirrors should you say you wouldn't drive your car without being able to hear the road?
More to the point mirrors on bicycles make less sense in heavy traffic or situations where the traffic will change from open road to crowded intersection and back again. It is easier -- and therefore safer by way of less complications -- for the cyclist to use his ears to hear what's coming from behind him. Using one sense for object behind and another for objects in front makes more sense than dividing your sense of sight between what's in front of you and what's behind, especially on a crowded street when you may need all your eyesight for calculating the trajectory of pedestrians, car doors about to open, cars pulling into or out of driveways, or even other cyclists.
CLOTHES
On yer back... Cycling or sports jersey of breathable fabric. This is a good start for any weather. In spring or summer when it’s hot, wear a zippered bike jersey, short sleeved. The zipper doesn’t have to be a full zipper even a half or quarter zipper will do; trust me, on the climbs or when the sun beats down, you’ll use if for venting. avoid cotton t-shirts which stay wet when you sweat. They are fine for going a few blocks; they will be uncomfortable after a few miles, especially if you are wearing a backpack or messenger bag.
In spring or fall -- a vest or light long-sleeved jersey, or sometimes a windbreaker. Really, though, a cycling vest is the most versatile of garments because it keeps you warm enough in most cases -- but can also be easily stowed in your pocket or in your bag, without much difficulty. Wear the long sleeve jersey over a short sleeve one, in case it gets hot and you desire to take it off you won’t have to go riding in the raw.
In winter, a long-sleeved jersey or thick shirt followed by a jacket; sometimes, in really cold weather, you can wear a fleece or warm layer vest underneath. The basic winter getup for longer rides is this; thin long sleeve shorts jersey, short sleeve cycling jersey, and long sleeve warm jersey either cycling or a warm thin layer. Then a cycling jacket. Depending on how far or fast you ride you might need less layers than this or more.
There are however two schools of thought on winter layers. In the old days the idea was a layer or two and a shell jacket, a sort of thick windbreaker without insulation but with resistance to wind and some degree, to rain or water as well. Nowadays, for longer or faster road rides, the trend is towards more layers and jackets for the outer layer that are “soft shell”, i.e., offer some degree of breathability and essentially fit like thick long sleeved jerseys. Both methods work but each works better in different situations. A cyclist riding short distances in very cold weather would do well to wear a layer or two under a shell jacket; for around town errands in weather 30 degrees F or so, a short sleeve jersey, a thin fleece, and a shell jacket works perfectly; the rider can unzip the inside layer or partially unzip the outer shell as he warms and cools, and he isn’t sprinting flat out up major hills for long distances so overheating isn’t so much an issue. A rider going longer distances or faster and harder is liable to overheat in such an outfit. For such a rider, the only major advantage the shell jacket has over the softer fabric construction of more modern “soft shell” jackets is some degree of water resistance – and sometimes the presence of front pockets.
In either case, a rider can always made up for some of the cold by adding a layer; this is where vests are useful. Also, keep in mind; some shell jackets have zip off sleeves allowing them to be worn as vests and making them more versatile.
Wool is useful in layering; it is often possible to wear a thin or midweight wool longsleeve jersey and a windbreaker and be warm down to the low 40s or thirties if you are moving. Needn't be cycling specific -- the Smartwool zipneck baselayers are great. And inexpensive... Find one at a TJMaxx or Marshalls and it'll cost you 20-odd dollars instead of 50-70 dollars.
But even at list price they are still cheaper than the hundred dollars or more paid for cycling specific wool longsleeves. So they lack pockets. You can wear a jersey or vest over it...
Speaking of vests, on America's increasingly harrowing roads you cannot be remiss to wear bright clothing. I have lately discovered safety vests which seem ubiquitous on road work crews. They aren't all the cheap mesh ones you seen before -- some are well made and suited as much to cycling as anything else. Even the cheap-o mesh ones can be useful, however. Although, the more practical vests are of the sort designated ANSI Class II -- such as seen here:
These fit more like a cycling vest; have a somewhat sturdier material, and reflective stripes going across, as well as up and down. In fact, Bike Nashbar makes its own version.
You will note in the example above that the lowermost reflective stripe would be visible to an overtaking driver below the level of my messenger bag. While these won't keep you warm like a cycling vest, they are useful in giving drivers something that stands out. The vest pictured above is from MSA Safety Works. It has reflective striping all over as well as a convenient little pocket in the back. The front Velcro closure is a bit wimpy, having only one spot of Velcro, but one can always add an extra Velcro attachment further down for the price of a few minutes effort, and a cyclist wearing a backpack or messenger bag will find that the shoulder strap of his bag helps keep the vest in place.
Another choice is to use a bright jacket. Blackbottoms Park City cycling jacket is neon yellow and very bright, to use one example...
Trousers or shorts: For around town riding pockets are your friend. Most bike shorts do not come with pockets. And, for shorter rides, although bike shorts are comfortable, they might not be worth it. We aren't concerned with style here, just utility. I typically wear cargo shorts or sport pants cutoff into shorts. For middle temperatures consider knickers. You can easily make a pair from an old set of cargo pants by cutting the legs off short, just below the knee, and re-sewing the edge. If I go to that trouble I typically also sew a piece of reflective striping to the left leg cargo pocket as well! A cheap and easy solution is to simply roll up the legs, but be warned; make sure they will not unroll. At speed if it gets caught in your chain you could have a nasty spill. For longer rides, bike shorts are a must. They needn't look like racer shorts; either; some mountain bike shorts are baggier and still fit comfortably on the bike over the long haul.
In hot weather, however, especially as the mercury gets to 80 or 90 degrees, cyclists will find that traditional tight-fitting cycling shorts are still their best friend; they breath, they dry quickly, and they are much more comfortable in hot weather. They do lack pockets, most of the time, but this can easily be remedied by using your rear jersey pockets, a hip pouch (avoid cheap "fanny packs" like you find at walmart, the this belts tear after a short while; use a small hiker's lumbar pack or a hip pouch made by a cycle messenger bag maker, like Reload or Freight Baggage). Also, a small pouch can be fastened to the shoulder strap of your backpack or messenger bag if you are using one, allowing easy access to items without rummaging around in the bag same as pockets in your shorts would.
Rain gear: in foul weather, rain gear starts with your bike. You do get wet from what is falling from the sky, and from passing vehicles splashing you, but most of what causes your clothes and body to get wet and cold when riding int he rain is water thrown up from the road. This doesn't just mean puddles that cause large splashes; riding in steady rain, even if it is not hard rain, will cause the tires of the bike to throw up a spray of water and dirt from the roadway surface, even if the surface is just wet, with no accumulated puddles or standing water. This can result in a comical -- or not-so-comical, depending on your humor -- brown strip down the rider's backside. It also invariably results in wet shoes. While the rear wheel throws spray up at your backside, the front wheel throws it against the bottom of the bicycle frame's downtube, where it is deflected onto the tops of your spinning feet. Even if it doesn't soak through your shoes it will find it's way in through the tops of them. Thus, the best rain gear starts with fenders on the bike. Following this, a good rain jacket is in order. Any waterproof jacket will work but for cycling for shorter rides; it will help if it has either a zipper or vents of both. Also it would help if it either has an elastic drawstring on the waist and/or elastic or adjustible cuffs. The jacket need not be bright colored; you can wear a safety vest over it, but it helps to get a jacket that isn't ninja black, either. For longer rides get something with riding in mind rather than just using what's on the coatrack by chance. Some companies like North Face, Columbia, Red Ledge, and Mountain hardwear, to name a few, make rain jackets suited to riding even though they are not cycling jackets. Others such as Pearl Izumi make cycling specific rain jackets. These can be fairly expensive -- figure a hundred dollars or so although you can get them on sale sometimes for like $80 bucks if you're very lucky. The main advantage of a cycling specific rain jacket is fit. They have a longer back to help protect your keister from water and grime that finds itself sneakign past your fenders, and they don't catch the widn like a sail because they have a more streamlined fit. A word on fit, however; a lot of bicycle clothing is sized for teeny weeny European souls with nicknames like "the Spanish flea" who live out of hotel rooms, stand on pdiums, and only weigh 140 lbs. When sizing bike clothes therefore check size. Especially from brand to brand; a medium size jersey or jacket in one brand may be large or even extra large in another. Nevertheless, the more bike-specific fit of cycling specific jackets makes them morth the outlay to anyone who rides for transportation. For sport rides on the weekend, one can make do with a thin water-resistant jacket you can stow in a pocket, or one of those plasticky clear rain jackets, but for longer riding in rain, especially if you have to go to work afterwards, it helps to have stuff designed for the long haul. Whether a bike company like Pearl Izumi or a regular outdoor clothing manufacturer like North Face, et al, look for taped seams, which keep out water, and waists and cuffs that can be cinched in some way. Cycling caps under helmets work great for the brims tend to help keep some driving rain from your glasses. Helmet covers are great, but if you run your auxilliary lights on your helmet not so much; however, you can wear one under the helmet, over the cycling cap. This is what I typically do. A person should probably keep a cycling cap on them if they bike to get aroudn regardless, since it is one of the most useful of items; it can shade eyes from sun, keep some chill off an otherwise bare skull beneath your helmet, or keep from rain off. Most cycling caps are not waterproof, however, which is why a helmet cover is a good idea, either worn under or over -- but the usefulness of the cycling cap cannot be ignored. Like waterproof jackets, waterproof pants are a must. I have a pair of rain pants that are not entirely waterproof but are fairly water resistant and i can ride home from work in a steady rain without getting wet. There are several kinds, but if you are commuting make sure you can wear them over regular pants, otherwise, wear them over shorts or knickers or tights as the temperature requires. You usualyl have to wear them over something besides just for shorts unless it is summer because although they keep the rain out, they do get cold and then so do you. Some of the pants have zippers at the cuffs; others have snaps or velcro. These help but you are going to have to cover them anyway. I have a pair of short leg warmers made out of the sleeves of a winter jersey for this purpose; they go from the ankle to 2/3 up the calf, just below the knee. You could tuck the cuff into your sock, but then the water would run down your sock into your shoe and you get wet feet. This way both are covered. Your hands and feet are the trouble areas. Most bike gloves are not waterproof; most shoes or sneakers aren't either. You could probably use a pair of rubber dress shoe rian covers, but even if your daddy's galloshes would hold up to the constant abrasions against pedals and toe clips without tearing they don't usually cover the tops of your feet. Some do, however, and if you have a pair, good for you. Otherwise get waterproof shoes covers. Bellweather makes a pair; I've used them and unless it's an absolute downpour they keep you dry. And if you have to you can put plastic bags over your socks. Also, regular winter shoe covers intended only for warmth do provide some resistance to water, whether by design or not, so in a pinch they are better than nothing, although they might lead to a defeat of their warming purpose when they do soak through eventually. Another option is waterproof boots, like gumshoes from LLBean; if they are too thick for fitting in toe cips adjust the straps or just ride the flip side of the pedals. For your hands, there is not much you can do unless you find a pair of waterproof gloves. Leather ones tend to be more water resistant in terms of soaking through, and sometimes you can get outdoor work gloves that are water-resistant. If you just have regular biking gloves take two pair, one for the ride out, one for the ride back. Also always bring a pair of dry socks in a plastic bag in your backpack if you ride to work; you never know. Nothing sucks like an 8-hour day in wet feet. For any thing that gets wet on the ride in, such as the outside of your shoe covers, your gloves, or your socks, wrap them in a paper towel and roll it up. Then press. Do this a few times then stow the stuff away wrapped up like that. It helps dry it out when you go to use it later. Lighting: Use lights on your bike. Bike lights have two purposes; being seen, and allowing you to see others, and the road. There are three main types; generator lights, battery lights, and rechargeable lights. The law says you should have a light on the front and back of your bike but this two-light minimum is barely sufficient sometimes and in varying conditions, or foul weather, not because the lights are not bright, but because htey are typically very small, and you are usually riding outside the center of the main lane where the driver is looking anyway. If you were dead center in his vision, that flashign rear light would be overkill; since you are off to the side where he won't look unless his attention is drawn, if might help to have two flashing rear lights, or one solid, and one flashing. Or mount the extra light on the back of your helmet. A cyclist *should* be safe using just one light on the front and one on the back, but until the drivers learn to pay more attention the carefull cyclist will have more than this, if only an extra flasher clipped to his helmet or bag, too. And as a general rule, for front lights it helps to have two; one solid, one flashing. Generator lights are very popular because they need no batteries; however, it is not possible to remove them without tools so a cyclist locking their bike outside leaves the lights on it, where they could be damaged. Also generators produce some drag on the hub, where the generating unit is typically located, although old-time bolt on units had a tiny roller that ran along the sidewall of the tire. Generators are nice, but fairly permanent in their attachment and also fairly expensive. Some swear by them; I've never gotten into them myself. Battery lgiths are the most common and most affordable; $30-$40 can get you a headlight and you can get taillights for $20 bucks or so, give or take. Outside of generators, most people use battery powered taillights, which typically run 2 AAA batteries. However, for headlights there is a mix between rechargeable and battery. Some battery lights can be as bright, and usually have the option of a flashign setting, where most entry-level rechargeable headlights only have a steady beam. However, the rechargeables, altho somewhat bigger, and more expensive [Nightriders entry level Minewt costs like $100 bucks compared to Cateye's basic battery headlight at under $50] you aren't buying batteries all the time, and the lights are usually brighter. Also they aren't much bigger; gone are the days of batteries the size of water bottles. Most of the batteries now are small enough to strap to the stem of your bike with a piece of velcro...
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