The Best Cycling Caps for Every Ride in 2021

Do cycling caps still have a place in today’s world? Marginal gains define the landscape of today’s modern cycling products. Helmets are almost universally worn and those helmets are a high-tech marvel. The technology packed in a top shelf road helmet of today is unlike anything in the previous history of cycling. Not only does it protect your brain but it makes you faster. 

Paired with these helmets are glasses that are aerodynamic and hydrophobic. They help make you faster and keep your vision clear. Another modern engineering marvel packed with technology and designed for marginal gains. Many cyclists of today take all of that design, engineering, and technology, and throw a relic from the 50’s into the mix. If that’s you then you know, if it’s not you then maybe consider it. 

From the very beginning of racing bikes there’s been a need for hats. Gravel cycling might seem like a recent entry into the cycling lexicon but it’s actually a revisiting of the early days. Before miles of pristine pavement cyclists took to the mountains and they needed protection from the elements. Hats helped keep the sun out the rider’s eyes and off their heads. They protected the head from the grime of the roads and helped keep sweat, or rain, out of the rider’s eyes. 

By the 50’s and 60’s the modern cycling cap had taken shape. The brim is short enough to see past when low on the drops and the whole cap fits in a jersey pocket without issue. The bright colors and distinct designs of modern caps morphed from the sponsored caps of the past. It’s a form that follows function. Even though technology has passed the cap by for many situations there is still a utility and style that dictates a space in your collection. Let’s take a look at some of the options.

Castelli A/C Cap

A hot weather option that’s great inside or out.

Material: 92% Polyester, 8% Elastane (Spandex) | Sizes: One Size | Colors: white, black, red

Covering the miles indoors with limited ventilation is a hot, sweaty, affair. Castelli introduced the A/C for hot summer rides but it’s a great option for indoor rides also. Any cap helps keep sweat from dripping into your eyes and the quick drying design of the A/C is especially helpful. The amount of sweat generated will quickly destroy a cotton cap. The synthetic construction of the Castelli A/C helps give it a fighting chance for a longer life.

Purchase the Castelli A/C Cycling Cap for $15.96 at Competitive Cyclist

Santini Trek-Segafredo Men’s Team World Champion Cycling Cap

For the world champion in all of us.

Material: 65% Polyester / 35% Cotton | Sizes: One Size | Colors: white

You can’t always take yourself too seriously. When I head out with some of the fastest hill climbers I know I sometimes like to grab my polka dots socks. It’s a bit of a joke we can laugh about no matter who gets to the top first. None of us are world champions but it’s a good laugh at whatever speed you ride at. You might also enjoy honoring the achievement of Mads Pedersen. Whatever the motivation, this cap from Trek and Santini is a very traditional style. It’s exactly what you picture if you picture cycling caps of days past.

Purchase the Santini Trek-Segafredo Men’s Team World Champion Cycling Cap for $19.99 at Trek

Sportful Fiandre NoRain Cap

A breathable and waterproof design keeps you warmer and dryer on wet rides.

Material: 50% nylon / 50% Polyester | Sizes: one size | Colors: black, orange

I’d like to think I’ve made a good argument for cycling caps in whatever weather you ride in. Still, the reality is that for many people cycling caps are an inclement weather item these days. If that’s you then the Sportful Fiandre NoRain Cap is a good choice for rain. There’s a degree of insulation, from the extra layer, but this is really a rain focused cap not a cold weather solution. Sportful has taped the seams and the fabric carries a waterproof, not water resistant, rating.

Purchase the Sportful Fiandre NoRain Cap for $60.00 at Amazon

Gore C5 Windstopper Cap

The right solution for windy rides.

Material: SHELL FACE 92% Polyester, 8% Elastane, SHELL BACKER 92% Polyester, 8% Elastane, STRETCH FABRIC 85% Polyamide, 15% Elastane | Sizes: one size | Colors: black

The Gore Windstopper solution isn’t waterproof. It’s water resistant but if you want something totally waterproof, look elsewhere. Instead, the design is totally windproof, extremely breathable, and water resistant. Don’t let that turn you away though. It’s a specific solution for a specific problem and if that’s your need then it’s a great option. 

If you haven’t used windproof products before the difference it makes is astounding. You can tolerate substantially cooler temperatures when there’s no wind chill. Without the challenge of being water proof there’s more breathability and the fold down flaps add even more warmth when you need it.

Purchase the Gore C5 Windstopper Cap for $49.02 at Amazon

Pearl Izumi Wool Cycling Cap

A simple and uncomplicated wool cycling cap at the forefront of sustainability.

Material: Main Body: 58% recycled polyester, 42% merino wool Other: 100% polyester Made in Vietnam | Sizes: one size | Colors: black

One of the negatives of this cap is that this isn’t a particularly warm hat. That’s only a negative if you are expecting a warm hat, don’t expect that here. The Pearl Izumi Merino Wool Cycling Cap isn’t meant for the coldest winter rides. Instead, it’s more of an all-around option that leverages the natural strengths of merino wool. Merino is excellent at temperature regulation in both cold and warm weather and that’s the idea here. The design is extremely thin for a comfortable fit and can be warm in a wide range of temperatures for most of the year.

Purchase the Pearl Izumi Wool Cycling Cap for $40.00 at Competitive Cyclist

Giro Seasonal Merino Wool Cap

A soft wool cap that feels like a warm hug on a cold ride.

Material: Cap: 94% merino wool 6% Nylon, Lining: 6% X-Static Fiber, 62% Polyester, 12% Spandex | Sizes: S/M, L/XL | Colors: Black, charcoal, heather red/black

The Seasonal Wool Cap from Giro is incredibly soft. It’s the kind of hat that feels like pulling on a warm hug. When heading out in mild but chilly weather, putting it on feels reassuring and comfortable. Seriously, it’s a joy to wear and it provides just that little bit of extra warmth. Don’t expect this piece to be the warmest thing in your arsenal but also don’t expect to wear it on a hot weather ride. It’s a perfect match to arm warmers and a summer kit all the way down to lightweight bib tights and a jacket. 

Purchase the Giro Seasonal Merino Wool Cap for $44.95 at Amazon

Should You Wear a Cycling Cap With an Aero Helmet?

With all the modern technology of aerodynamic helmets the question arises, does it make sense to wear a cap with an aero helmet? Bottom line, no one can dictate what you do. If you want to wear an aero helmet and a cap go for it. The question still lingers though. Aero helmets generally cost more so maybe you should save money if you like wearing a cap?

I’d suggest that an aero helmet gives you greater flexibility. For the fastest days, or a race, you might choose to leave the cap at home and go for whatever marginal gains you can. When average speed matters less grab your favorite cap. If you choose not to buy an aero helmet from the start you lose out on the flexibility to make the choice. 

How to Wear A Cycling Cap?

This is a big one. Cyclists are an opinionated bunch and how you wear your hat is a big deal. Friendships may have ended because of this question. Or no one cares, but it’s fun anyway. In the heyday of cycling caps there was a specific way to wear them. Even then different people had different interpretations but if you fall on the side of tradition then there’s a specific way to wear them. Keeping the tradition, will dictate brim down and the back of the cap a little high on the head so as to create some space above the top of your head. 

Some people would argue that traditions only survive if they adapt over time. A tradition that’s frozen in time is a dead tradition on its way to obsolescence. In the 90s the cycling cap entered the realm of general fashion. It was a street fashion trend rocked by Wesley Snipes in “White Men Can’t Jump,” Spike Lee in “She’s Gotta Have It”, as well as seemingly every urban bike messenger. In this incarnation the correct way of wearing a cycling cap was tight on the head with the brim flipped up. It was also somewhat divorced from cycling and as likely to be on an actual cyclist as not.

Given that most people think cyclists look ridiculous I say don’t worry too much. I have a saying that goes something like, “Socks should be tall, legs should be smooth, and collars should be stiff.” Lots of people disagree with me but it’s what I like. Do what makes you happy and make your own style. Always make sure you have your cap straight though. There’s definitely no leeway for cycling caps with a crooked brim.