1. A cotton shirt and a jersey-knit blazer provide comfortable, breathable layers that keep your look dressed up without restricting your range of movement. Blazer ($795) by Luigi Bianchi Mantova Rough. Shirt ($325) by Calvin Klein Collection. Pocket square ($135) by Brunello Cucinelli.

2. These slim, durable slacks have the water-resistant properties of a windbreaker, plus a bit of stretch thanks to a blend of cotton, nylon, and elastane. Pants ($225) by Outlier.

3. You can't get any more bike-appropriate than white canvas sneakers, which serve as a neutral anchor for any outfit and just get better with a little wear and tear. Sneakers ($60) by Tretorn.

1. A soft crewneck sweatshirt will keep you warm without overheating and is made to withstand the rigors of athletic activity. Sweatshirt ($575) by Brunello Cucinelli. Sunglasses ($290) by Marc by Marc Jacobs.

2. These cargos are trim rather than billowy, upping your style quotient and helping keep cuffs from getting caught in your chain—plus, hidden zippers let you turn them into shorts in an instant. Pants ($140) by Club Monaco.

3. Stripped-down leather sneakers with chunky textured soles provide the perfect combination of comfort and stability. Sneakers ($100) by Adidas.

1. A super-thin-gauge tee made of naturally moisture-wicking merino wool will keep you from getting sweaty while shielding you from the sun. T-shirt ($77) by Sunspel. Watch ($4,100) by IWC.

2. Trousers can have bike-friendly details—like reflective tape inside the cuffs and a waistband strap for your lock—without shouting weekend warrior. Pants ($78) by Levi's Commuter Series.

3. Multicolored mesh running shoes with thick rubber soles not only look cool—they provide your feet with solid traction and support. Sneakers ($120) by Nike X Undercover Gyakusou.

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Also on Details.com:
The Look of International Cycling Chic
Cycling Nation: The Ultimate Buyer's Guide
The Perfect Biking App