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Best waterproof and winter cycling caps

Warm and waterproof winter cycling caps to prevent brain freeze

Cyclist magazine
8 Mar 2021

Waterproof and winter-condition cycling caps, is it possible to stay both warm and stylish? For the summer, even the most basic casquette will add a little French cycling style.

However, when it comes to winter riding, designers have struggled to come up with a look that adequately fits the term ‘classic’. Yet we think it’s still possible for the cold-weather cyclist to maintain a bit of chic while keeping themselves from freezing.

Hopefully, after browsing what we consider to be the best waterproof and winter cycling caps you’ll agree too...

The best waterproof and winter cycling caps

1. Best all-round winter cycling cap: Bontrager Thermal Cycling Cap

Buy now from Trek for £17.99

This simple uni-size cycling cap from Bontrager scores well on all counts. It’s easily thin enough to slip under a helmet, it covers your ears, it doesn’t cost too much, and perhaps most importantly, it doesn’t look kooky. Made of soft and stretchy thermal fabric, it’ll do for all but the very coldest days, or serve hotter heads all through winter.

Looking very normal to start with, its full-length peak ensures it keeps the sun out of your eyes while embodying all the style of a regular cycling cap. With a brushed interior to its fabric, for cold days its double-layer ear flaps can be rolled up to help regulate your temperature.

A diminutive item that’s versatile and small enough to chuck in a jersey pocket, the Bontrager thermal cycling cap suits conditions from fresh to Baltic, meaning in the UK you might well get three seasons of use out of it.

Buy now from Trek for £17.99

2. Best deep-winter cycling cap: Endura Pro SL Winter Cap

This Belgian-style winter cap is made by Scottish brand Endura. Unsurprisingly, it’s very good at keeping out foul weather. Ideal for those rainy deep winter days that I like to spend in bed with the paper, but some people insist on riding through, it’s quite high-tech in its construction.

Melding together plush Thermoroubaix panels, key bits of its exterior are also wind resistant. Coated with a DWR treatment to further keep out the elements, its rear flap covers all of your ears before extending all the way to the top of your jacket collar. Combined with a decent-sized peak, the feeling is one of being well swaddled away. Reflective racing-stripe style strips run front to back give a bit of extra visibility on grim days too.

Available in two sizes, you’re better sizing up rather than down. Either way, a fit that’s slim given the level of protection offered ensures it’ll slip easily under a helmet.

3. Best cap for racers: Sportful Fiandre NoRain Cap

Ever wish your regular cycling cap was waterproof? This is what it would look like. As stylish and inconspicuous as any other casquette, the NoRain cap uses the same waterproof and breathable fabric as the rest of Sportful’s Fiandre range.

With taped seams, no water will make its way through, but the excellent breathability of the fabric means you won’t sweat either.

There’s no internal insulation or extended ear flaps, so don’t expect it to keep you too warm. A very useful, if slightly niche item, its good looks go some way to justifying its high price.

4. The most stylish winter cycling cap: Rapha Pro Team Winter Hat

Buy now from Rapha for £45

Decent looking yet pleasingly technical, this hat from Rapha features a waterproof exterior that protects its softer fleecy interior.

Breathable enough to stop you from getting too sweaty, yet warm enough for Baltic conditions, the back is less windproof to allow the back of your neck to let off steam.

Extended towards the back, this extra flap also keeps the majority of your ears covered, while ensuring the whole thing stays in place.

Using flat-locked seams and a multi-panel construction, it’s not too bulky to slip underneath your helmet. However, you’ll need a little bit of spare space there to make this a comfortable experience. Similarly, coming in two sizes, make sure you pick the correct one as there’s only a moderate degree of stretch to the hat itself.

Using a soft peak, the whole assemblage is relatively fetching. Practical too, reflective piping the whole way round is backed by a broad and equally reflective Rapha logo across the back to keep you visible to traffic. 

Buy now from Rapha for £45

5. The best softshell winter cycling cap: Castelli Difesa2 Cap

Difesa is the Italian word for defence and it’s an apt name for this bit of headgear. The initial impression this cap gives is that it’s too thin to be of much cop when temperatures drop, but the entire thing is constructed from the same material Castelli uses on its rightly celebrated Gabba jersey – Gore’s Windstopper fabric. Meaning this will protect you against both the wind and rain while also being highly breathable. 

It can be worn like a regular casquette, with its traditional cycling cap visor working to keep the rain out of your eyes, but there is also a fold-down panel made of Thermoflex fabric which can be deployed when the wind starts to bite that’ll keep your ears from falling off. Reflective piping around the sides and detailing embedded in the Castelli label to the rear complete the package.

Available in one size, the material feels stretchy enough to fit all but the biggest of heads. 

6. Best for riders who don't mind cold ears: Sealskinz Waterproof All Weather Cycle Cap

This cheap and good looking cycling cap wears its waterproofing lightly. Easily slim enough to fit under a helmet, its three-layer waterproof, windproof and breathable construction doesn’t add as much bulk as you might expect.

Insulated on the inside, but without any additional protection for the ears, it's good for cool days, or people with above-average circulation to their ears. Coming in two sizes, if in doubt go one up as its fit is fairly snug.

A normal looking cap, that’s both waterproof and insulating. Good for cold weather, you might feel the lack of ear flaps on the nippiest of days.

7. The best cycling skull cap: Castelli Estremo WS Skully 

With a band made from Gore’s Windstopper X-Free fabric, the Estremo WS Skully does a fine job of keeping your noggin snug, forming a protective chill-proof barrier that wraps itself around your forehead and over your ears.

The rest of the cap is made from a fleecy, elasticated material called ‘Warmer Fabric’ which isn’t windproof (because it’s used in places where it doesn’t need to be, as long as you’re wearing a helmet over it) but it is highly breathable, offering a comfortable – if somewhat close – fit.

Castelli reckons this is suitable for riding in temperatures between 5-10°C, but we reckon it’d still serve you well in temperatures below that. The Italian firm also bills this as a skullcap, despite it not quite fitting the accepted description of that on account of a wee flap at the back of the cap.

Acting almost like a reversed peak, this serves to protect the exposed part of your neck between what would ordinarily be the bottom of the cap and the top of your jacket.

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