1. Cycling clothing theoretically comes in three varieties:
As you could guess this means tight spandex clothing, looser clothing (with some other big players in the field), and practical clothing like rain pants that zip over your regular clothing.
From now on, since I am primarily a road cyclist (since 2007) I will focus on road issues.
For women's cycling clothing there is a really large variable at play:
It is entirely possible to have very functional cycling clothing also look good, but a lot of cycling clothing manufacturers seem to think that women ride for an hour or so, perhaps at 10 mph along the beach front without a helmet. The rationale behind making clothing for women who ride seems to often be appearance first, functionality second (actually this is true of women's clothing in general-- like our generally non-functional pockets). Because the "Instagram cyclist" doesn't want to be seen in the same cycling gear in each shot, companies enter the market to produce cute, barely functional or non-functional mix and match items to dress up in like bike-dolls. It's tough as a new cyclist to avoid these crappy items, but you need to. But it's hard. Especially because marketers try hard to sell you almost anything and the good stuff that you need might seem ridiculously expensive. Also, we can all be suckers for a cute looking item (more on that later).
2. When you buy cycling clothing (if you're riding seriously and not doing a 3 mile commute that you could do in almost any clothing, weather-dependent) you are generally buying two items:
In this photo I'm not wearing cycling length socks (I often don't as I hate weird tan lines) but otherwise this is very standard-- a real kit, matching jersey and bibs. A lot of people really try to wear matched clothes like this. Photo by Dasz Haagen.
Bibs: If someone is trying to sell you shorts, they probably think you're spending more time in the coffee shop than riding (they're insulting your intention to ride seriously). Bibs. Bibs are the way to go. Shorts just do not cut it. Why? Shorts bind at the waste, they move around displacing your body from the proper position on the chamois, they allow gaping in back, they allow bad drafts in the winter time, and so on. Bibs can be an issue for bathroom breaks, but seriously, how often do you pee on your ride? Can't you take off your top(s) to shuck the bib straps during your outing, if a break is needed? Also there are (higher priced) bibs that allow you to have a potty break without taking off your tops(s). [One good point for shorts: they allow you to wear tank-top style tops and avoid some of the awkward tan lines most cyclists cultivate in the summer].
Your bib cannot be unisex, and a man has different equipment down there-- where he needs padding is not where a woman needs padding. Buy a women's bib with a chamois. That's the special padding in the crotch. The quality of a chamois is what will make the difference in how long you can be comfortable on the bike. Your chamois must be melded to your body. If it sticks out like a diaper with a mind of its own then you're buying a bad quality item, or at least the wrong size. Your bibs have to be the right size or the chamois will not be where it should be. And, sorry about this, but the right size is basically skin tight. You can choose to wear the correct clothing, or you can choose to hide the parts of your body you wish weren't obvious in skin tight clothing. I try to just get motivated to ride harder/longer when I look down and see something that's not ideal.
It is possible to buy special shorts with a chamois that are meant to be worn under other clothing, secretly. These can be useful for commuting, for example. Some mountain bikers wear these under loose non-cycling-specific clothing. There are also cycling specific clothes sold without a chamois. My best winter fleece-lined cycling tights have no chamois, so I wear bib shorts over those tights. But if you're riding more than a short commute, you want a chamois. You probably need bibs with built in chamois. Also, this is important-- you do not wear underwear with your chamois. The whole point of a chamois is to make it so you are NOT riding on uncomfortable seams and lumps. Chamois have different cushioning based on where in your seat region your bones are closest to the skin, and they also have been designed for air venting and what not so you're not sitting a pool of sweat. If you wear your undies with those seams under your chamois, next to your skin, you're defeating the non-chafing, no-seam, air flow purpose of the chamois. Would you wear underwear under your swimsuit? If you are just getting into cycling buy one good part of bib shorts, and wash them after each ride. The good news is that they dry super fast. Washing often (hand washing preferred, although I'm too lazy) is a good idea because of the whole bacteria situation with sweat and what not. You'll have fewer saddle sore issues if you always wash your body and your chamois after each ride.
Jerseys: Do not buy a jersey that doesn't zip all the way (such as a pullover, a neck zip, or a 3/4 zip). You want to be able to open that jersey up to get air when it gets super hot (not all the way, but partially) and your pee breaks when wearing bibs will be even more awkward if you don't have full zip. Cheap jerseys will have zipper penis (when the zipper sticks out in the middle for no reason). Bike specific jerseys will have 3 or 2 (esp. if you're an XS or S) pockets at the lower back. These pockets are super important. They need to hold your essentials on the bike, so they can't be too loose, but they need to hold the stuff, so they can't be too small or too shallow, either. Your jersey has to fit tightly or it will whip in the wind, causing you to work harder and also making you look like you bought a parachute instead of a jersey. In the bizarre logic of cyclists having your vest whipping in the breeze is somewhat acceptable, even though this also causes drag, but your jersey, as the layer that's quite close to your skin, should not billow. If it's too loose it will even twist on your body in the direction of the heavier things in your pockets. So if you have an orange back there, or a multi-tool, it will try to rotate until that's closer to your belly. This is uncomfortable and unsafe. Buy a proper jersey (tight). One way you can tell your clothing is crappy is when you buy a medium and it fits on your body like a medium blouse. It's not a blouse. It's for cycling. If you're a medium, then a medium should be skin tight.
Here I am wearing a tight fitting gillet from Rapha that makes me look a little like a stuffed sausage. And snowboarding socks because it was hump season. Also, please note that having some bright items (like my shoes and vest in this photo) really help make you visible on the bike. Too many bike items are black. Photo by Dasz Haagen.
Other cycling clothing:
What else might you want to invest in, if you are just starting out? Well, you should buy arm and knee warmers. Knee warmers are worn under your shorts and go from your upper thigh to your mid calf or so. Arm warmers are for wearing with short-sleeved jerseys, and these also should be worn under your jersey going from your armpits to your wrist. You can buy arm covers that are not insulated for wearing in the summer to avoid too much sun. But the reason to have arm and knee warmers is that you can easily take them off after the day warms up and stick them in your pocket. You could also benefit from a vest. Vests or gillets (if you want to feel all Euro) can be stuck in a pocket easily, too. They often don't have their own pockets to make them less bulky when you pack them up. Super close fitting beanies to wear under a helmet or stylish socks (should come up 5 to 7 inches from the heel) are also items a lot of cyclists own. The beanies are good for cold mornings and the socks make another awkward tan line, which cyclists often aspire to.
Photo by Leo Rhee in 2016, I'm wearing not insulated arm covers.
Also, buying appropriate gloves is a must. I own three types of gloves at all times. For the warmest summer months I have fingerless gloves, basically mesh on the back, absorbent for wiping sweat. For the hump seasons I have long fingered gloves that protect my arthiritic joints. And for the winter I have giant lobster claws-- very warm. The gloves let you cultivate another bizarre tan line at your wrist, and also I get them with padding in the palms to relieve the pressure of too many hours gripping and leaning into the handlebars. Some people who don't ride as long, or use a very different riding position don't use the padded palms.
You have to buy cycling shoes, if you intend to be efficient on the bike. The problem is that cycling shoes mean also buying cycling cleats that match your pedals. Seriously, you need to coordinate these three items. If you live in a warm area, your feet sweat a lot, or you ride mostly in the summer, you probably will be fine with a pair of regular shoes and maybe some shoe covers for the colder months. If you live in a real cold area, or ride even in really bad weather you may want some winter riding shoes/boots. I have both.
Shoe covers come in different varieties, mine are not insulating, they just block water and wind (to some degree)-- I have winter riding shoes that don't have vents. I picked these shoe covers because they are highly visible. The tendency of cycling clothes to be black or dark is really dumb-- be visible and stay alive! It can be hard to find bib tights in any color other than black, but I try to stay visible. You can't see it on the long-sleeved jersey I'm wearing from this angle, but there is a bright pink stripe down the center of my back. I'm wearing a cap with a little visor under the helmet because it was raining.
If you're riding in really cold weather, a neck gaiter can be useful. Some people use masks, or wear their snowboard goggles in the winter.
3. A ton of cycling clothing is not worth the money, even when it's deeply discounted. Seriously, there is some real trash out there. I think part of it is to take advantage of people (men or women) who are just starting out who haven't realized the benefit in buying the expensive stuff yet. But a lot of it is just... the same brand for men will be a HUNDRED times better. They really think that women just want to look cute.
I keep wrestling with these because they are my only pair of over the bib knee warmers as an extra layer in midwinter. BUT THEY ROLL THEMSELVES DOWN. I literally have to pull them up every couple minutes.
I had this idea that I wanted to get a tank top so I could get sun on my shoulders and avoid tan lines. The problem is that in riding position I look like I'm just displaying my cleavage to oncoming vehicles. So I bought a "bolero" to wear to cover that area, and your arms and what not. BUT look below-- you zip it closed and you are STILL showing off your cleavage. SO EMBARRASSING, because it looks intentional. The bolero is Louis Garneau, which is a pretty good cycling gear brand for men, but doesn't take women seriously.
I bought a pair of leg warmers with a nice pattern-- polka dots! In the first photo they've made it from under my shorts to starting to fall down on one leg. FIVE MINUTES into the first wearing-- when they should be as tight and grippy as they will ever be. The second photo shows about 15 minutes in-- totally past the knee on one side. Are you kidding me? Are you selling leg warmers that have no interest in staying on legs?
These are Castelli, a brand famous for being too tight. So I bought a large instead of a medium. First, they are too big in the front (on the saddle it's even worse-- there's a shelf of fabric in front. And the rear view? Oh my gosh. PLEASE, this is embarrassing. The same red fleece lined Castelli winter bibs are favorites of every man I know who owns them, but as you can see the front view and the back view are both just unacceptable-- the front because the chamois is in the wrong place, the back because I have literally never worn cycling bibs so unattractive.
4. So how do you reliably get good cycling clothing?
I hate to say it, but you buy the brands that actually understand women's bodies and take women seriously as cyclists. I have not tried all the women's cycling companies.
The absolutely top recommendation I have is Velocio because they actually care about women. Sign up for their mailing list so you get notified about final sale items. Literally it's too expensive to buy their clothing if they aren't on sale.
Hincapie clothing is harder to find these days, I think they've lost a lot of their spot in the crowded market, but everything I have had from them is really good. Including bib shorts. When I rode for UCLA all our kit was Hincapie. I still use many of those pieces cause they last!
Rapha is sort of the industry leader, but now it's been bought out it has lost some of its cachet. They do a couple big sales a year where with 40 or 50% off you can actually afford the clothes. Some of my clothes are Rapha, but unlike Velocio everything I buy isn't great-- it's solid, but not reliably amazing, Seriously Velocio is amazing.
Do not buy Primal, Canari, Castelli for below the waist (and wear a size up from your regular above the waist), and probably a lot of other brands, too. My Giordana bib tights were good, but now the inside of the chamois came loose, and I had to have my mom unstitch, reposition, and restitch the bibs. It's obvious that happened, and I doubt they'll last much longer.
If you want to look bad ass, there is also Betty Designs. I still haven't bought anything, but some of it's so awesome looking. I think I need a sponsor to afford it because it's never on sale.^^
Popular brands with my (male) riding friends right now include Rapha, Pas Normal Studios, Assos, and Ale. And people do buy Gore (for winter, especially) and Castelli, too.
I have a pair of bibs that are designed for extremely long cycling journeys in quite hot weather made by Red White, a two-man company from Singapore. I have been in contact with them for quite a few years now, and given a lot of feedback on designs and colors. These are my Red White bibs, but i have them rolled up (tan lines... just like the sleeves of the red Velocio jersey are rolled up).
5. Why are cycling clothing items so darn expensive?
Part of this is that you get what you pay for-- the expensive stuff really does do the job better. But a lot of it is because right now road cycling has become in some circles and some parts of the world the "new golf." In other words, it's a sport that the rich get into with super expensive everything right from the get go. I mean they buy a bike for 10,000 before they even know if they like cycling. So bib shorts that cost 200 don't actually seem like much to them.
But for the person with a smaller budget, just buy 1 bib short and 1 jersey, and wash them as soon as you get home. They'll be dry by tomorrow.