Cycling is a tradition-rich sport with over 100 years of racing and cultural history. New cyclists should do their best to be mindful of the history and etiquette surrounding the sport when first starting out because it can sometimes be hard to know what gear is appropriate and what is unnecessary.

Your kit should fit snug, but not this snug.
I’ll preface this by stating that practically any form of cycling is generally good and you should ride in whatever manner makes you happiest. If you don’t care what you look like when you ride, just keep on doing what you’re doing. But here are some fashion guidelines to follow if you want to avoid looking like a total noob. This list is not comprehensive (see The Rules of the Velominati for a more thorough examination of cycling etiquette), but it should help get you started.
1. You don’t have to match, but your clothes have to fit
Matching your jersey/shorts/socks/helmet will definitely make you look cooler and possibly faster than you are, but it’s not an absolute must. The unwavering truth however is that your jersey and shorts must fit. If your shorts are so old that the leg bands aren’t skin tight around your thighs, time to get rid of them. If the elastic in your shorts won’t stay up on its own, you are required by cycling law to invest in a new pair. Your jersey must also fit tighter than a T-shirt, but not too tight so as to constrict breathing. When you try on cycling clothes, sit down on a bike to see how they fit while in the riding position. Using this technique should ensure that you buy the correct size.
2. Never, EVER wear underwear under your cycling shorts
The chamois in your shorts is designed to work next to your skin. Its primary purpose is to reduce friction and its secondary function is to provide some cushion. Wearing a pair of cotton tighty-whities under your shorts completely defeats the purpose of the chamois and could result in some extremely painful and embarrassing saddle sores. It is acceptable to wear layers over your shorts, such as chamois-less tights or knickers, but never wear anything under your shorts or bibs.
3. Don’t hang out in your racing kit
As cool as you may look on your bike in all your gear, you look equally uncool off the bike in public places in all your gear. Try to avoid lounging in coffee shops, grocery stores and other cyclist hangouts kitted out in your Lycra skimpies. This rule holds true at races. Triathletes are usually the worst offenders. Consider this rule as a third transition. As soon as your race is over and assuming you are physically capable, your priority should be to get back to your car where you can change out of your sweat-stained onesie and into some casual clothes. Never linger in your kit.

Hi-Viz apparel should only be worn in low-light riding conditions.
4. High-Visibility Apparel is for dawn and dusk
I know there are plenty of people who wear hi-viz gear all the time and like I said above, do whatever makes you feel good while riding, but to avoid looking like a Fred, heed my advice and reserve the bright yellow for low-light conditions (if you don’t know what a Fred is, you could be one and should click here). Think about it, wearing bright yellow in the middle of the day while riding against a background of green hills may actually make you blend in more to the eye of a motorist than if you had a black or white jersey on. Hi-viz apparel has its place – I’m not slamming the premise of it – just try to avoid wearing it when it’s not needed.
5. Invest in proper cold weather gear
- Arm warmers should never be worn with a sleeveless jersey
- It’s ok to wear arm warmers without knee warmers, but don’t wear knee warmers without arm warmers. It looks weird.