I don’t race bikes; I ride them. Maybe it’s because of this distinction that for the longest time, I was reluctant — no, resistant — to don the form-fitting kits that are universal to cycling, the sport. A good many of the miles on my bike are logged between home and the office, but longer rides have been a part of my fitness regimen since college when I’d regularly cap off a week with a 30-mile ride on Friday afternoon. My bike: a 1970-something Motobécane inherited from my mom; my kit: a cotton t-shirt and running shorts. Looking back, both now seem markedly inadequate to the task.

Years later, after recently relocating to New York City, I was invited to join a friend on a 50-or-so mile ride. We would spin up Manhattan’s West Side Highway, across the George Washington Bridge into New Jersey and up along the Hudson River to a watering hole called the 9W Market. On any given Saturday the clientele here is dominated by kitted-out cyclists; my compliance, I was told was requisite.

We made this journey on a frosty November morning, and my shorts and tee wouldn’t have cut it in the low temperatures, so I acquiesced out of equal parts necessity and conformity. Pulling on my stretchy leggings, I felt as though I was suiting up for an expedition to the outer atmosphere. I also worried: that my greenness would show throw my snazzy gear via my unrefined form in the saddle, that I’d feel fettered by the restrictive elasticity of the skin-tight clothing. The reality turned out to be the opposite.

Why wear cycling clothing? The only reason I need is comfort. My old gym bag outfit was serviceable, but a fully-fitted cycling-specific kit is functional. It’s made for riding bikes. The fabrics provide padding and stretch where it’s needed, and the silhouettes are designed to move with the body as it powers over the pavement. Riders wear it to be comfortable, not to look cool — but buy from the right brand and you can get both.

Black Sheep Cycling

Sometimes cycling takes itself too seriously. But that’s not Black Sheep, a young cycling brand from Brisbane, Australia with a growing worldwide following. The company preaches individuality over conformity and produces a collection that supports the ethos, pairing high-quality materials and manufacturing with alternative patterns, like the Breton stripes of Team Collection Jersey. “Fuck the stereotypes, just do your own thing,” Black Sheep says (with a grin and a wink).

Ventral SPIN Helmet by POC $290
Do Half Blade Clarity Sunglasses by POC $260
Team Collection Men’s Stripes Light Blue Jersey by Black Sheep $140
Essentials SS Men’s Navy Bib by Black Sheep $170
Perfect Crew White Signature Sock by Black Sheep $20
R1 Infinito Knit Shoe by Fi’zi:k $450
S-Works Venge by Specialized $12,500


Designed with New England gumption and made in Italian mills, Velocio apparel finds its roots in the fit and performance at its core. Toward its exterior are more tangible characteristics, like unique patterns and the endorsement of pro cyclist Ted King. It makes for a kit that isn’t vain or flashy but looks good and performs even better all the same.

Aether MIPS by Giro $325
Delta TG ML Beetle Sunglasses by Alba Optics ~$198
Tricolor ES Jersey by Velocio $179
Luxe Bib Short by Velocio $259
Tricolor Signature Sock by Velocio $19
P.R.O. Leader v4 Cycling Shoe by Pearl iZumi $350
Ultimate CF FL Disc 8.0 by Canyon $2,799


Chances are you’ve heard of Rapha. Rapha is the reason why so many riders around you are wearing electric pink. Every piece of apparel, from head to sock, is designed as the pinnacle of its category. You might not know it though — the brand’s Creative Director, Alex Valdman, favors simplicity, advocating the idea that the best cycling apparel goes completely unnoticed when worn. He means by you, the completely comfortable and chafe-free rider. Others are sure to notice, as you speed by for a pass.

S-Works Prevail II Helmet by Specialized $225
EVZero Stride Sunglasses by Oakley $173
Classic Flyweight Jersey by Rapha $135
Classic Flyweight Bib by Rapha $150
Lightweight Socks by Rapha $12
S-Phyre RC9 Shoe by Shimano $400
Madone SLR 6 Disc by Trek $6,000+

Note: Purchasing products through our links may earn us a portion of the sale, which supports our editorial team’s mission. Learn more here.