What to Wear Cycling

For your first few rides, wear what you already own. Anything without a seam down the middle of the seat, a top that is not cotton, and shoes with a firm sole. Plus a helmet, which is the one thing not to improvise.

Then buy padded shorts, and nothing else, and see how you get on. That is the single highest-value clothing purchase in cycling by a wide margin, and everything below is about what comes after it.

The three rules that matter more than any garment

1. No cotton

Cotton absorbs sweat and holds it against your skin. On a warm ride that is a heavy wet shirt; on a cool one it is why you get cold the moment you stop pedaling or start descending.

Any technical synthetic or merino works. Wool is genuinely good at this — Woolmark’s published fiber data describes it absorbing a large share of its own weight in moisture vapor without feeling wet, and their odor research explains why wool stays wearable longer between washes than synthetics.

2. No underwear under padded shorts

The pad is designed to sit directly against skin. Underwear reintroduces the seams the shorts removed and traps moisture, which is how chafing starts. Everyone has to be told this once.

3. Dress to be slightly cold for the first mile

The universal winter mistake is dressing for how it feels standing still. Ten minutes in you are too warm, then you sweat, then the sweat cools and you are colder than if you had dressed lighter. If you are comfortable in the driveway, you are overdressed.

The temperature table

Starting points rather than rules — personal tolerance varies enormously and you will calibrate within two or three rides.

What each item is actually for

Padded shorts — buy first

The pad is not a cushion for a hard saddle. It removes the seam that would otherwise sit exactly where you do, manages moisture so skin under pressure stays dry, and spreads pressure a little. All three matter, and the first is the big one.

Bibs or waist shorts is a separate decision — roughly, bibs above an hour, waist shorts below.

A jersey — buy second, or never

The functional argument for a cycling jersey is three rear pockets. That is where your phone, keys, food and spare tube go when you have no bag, and they are at the back because that is the only place on your body that is not compressed when you lean forward.

If you carry a bag on the bike instead, a technical running shirt does the same job for less.

Arm and leg warmers — the underrated purchase

For about $25 they turn kit you already own into kit for a 20-degree wider temperature band, and they come off mid-ride. If you are buying one thing for spring and autumn, buy these rather than a second jersey.

A windproof jacket — for below about 55F

Windproof, not necessarily waterproof. At 15mph you create a 15mph headwind, and that air movement strips heat straight through fabric that is merely thick. A thin windproof shell beats a thick fleece, which is the opposite of most people’s instinct.

A full-length zip matters more than it sounds: it is how you vent on a climb without stopping.

Gloves, ear cover and shoe covers — the extremities

Riding generates plenty of heat in your torso and legs and almost none in your fingers, toes and ears. Those are also the parts most exposed to the wind you are making. In the cold, the extremities are the whole problem, and $35 of shoe covers and a helmet liner does more than a $200 jacket.

Rain

The honest position: in warm rain, do not bother. Fully waterproof fabrics do not breathe well, so on a warm day you end up just as wet from the inside and hotter with it. Get wet, and dry off afterwards.

In cold rain, a waterproof shell is genuinely necessary, because wet plus wind plus cold is how a ride becomes miserable and then unsafe. Add mudguards if your bike takes them — most of the water hitting you comes off your own front wheel, not out of the sky.

Sizing, and the trap

Cycling clothing runs one to two sizes small, because it is cut to fit closely in a riding position rather than standing up. Read the manufacturer’s chart every single time, and do not assume consistency between brands.

Jerseys and jackets are also cut with a drop tail— longer at the back, shorter at the front — which looks odd on a hanger and is correct on a bike.

What order to buy in

1. A helmet— not clothing, and non-negotiable.
2. Padded shorts— $30 to $50, and the biggest single improvement.
3. Gloves and sunglasses— about $40 together, and they fix two specific common complaints.
4. A jersey— if you need the pockets.
5. Arm and leg warmers— the cheapest way to extend the season.
6. A windproof jacket— when you decide to keep riding into autumn.
7. Winter extremity kit— when the jacket stops being enough.

You do not need any of items 4 to 7 to be a cyclist. Plenty of people ride all summer in shorts and a running shirt, and that is a completely legitimate way to do this.