How to Look Cute on a Bike without Really Trying

How to Look Cute on a Bike Without Really Trying

Four outfits for every type of ride.
By Sam Reed
Jun 09, 2021 @ 8:00 am
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Last summer, a friend of mine ordered a bike online. The model she chose was nothing fancy - just a cute, easy commuter for brunches in the city or leisurely rides around the park. It was silver. Two months later, the bike finally arrived from somewhere in the depths of Eastern Europe (the cost of shipping was nearly as much as the cost of the bike itself). It came in parts and required professional assembly at a local bike shop for an additional fee. I thought she was crazy.

But, by mid-July, she was zipping around town while thousands of other bike-less Americans stood by on domestic waitlists, yearning to get their hands on what was by then considered a precious commodity. Like sewing machines, toilet paper, and suburban starter homes, there weren't nearly enough bikes available to meet the early quarantine demand. This shortage, which is likely to bleed into 2022, was due in part to interruptions in the supply chain as well as, of course, lockdown fever. When public transit and even some local parks and beaches were closed, many amateurs who may not have ridden a bike since childhood were looking for something, anything to do outside. 

The biking revolution - which began prior to the pandemic due to the rising popularity of e-bikes, local governments' commitments to making cities more bike-friendly, and the appeal of biking's non-existent carbon footprint  - was now in full swing. 

As with any revolution, though, my friend and I had one question: How can we look cute while doing this? Go ahead, judge me, but if I choose to ride my bike to brunch, the last thing I want is to arrive looking like a wet rat, sweat dripping down my leggings, hair either plastered to my skull or haywire from wind.

Recreational cyclists have different priorities than road cyclists with their aerodynamic, breathable helmets and spandex shorts suits and testosterone scandals. Many of the traditional cycling companies can seem intimidating, intended not for the crop top-wearing occasional commuter but for triathletes and Iron Men. It's not a leap to say that quarantine changed that. 

Ely Khakshouri is the CEO and founder of LA-based brand Retrospec, which makes minimalist bikes and e-bikes inspired by fashion and lifestyle trends. "One of the things that has been really attractive to me about the bike industry is just how little great design there is," Khakshouri tells me. "I think that so many of the legacy bike brands are designing for the avid cyclist and the bikes all kind of feel the same. And in many cases they feel kind of intimidating and they don't really match other aspects of our lifestyle, other things that we consume and other things that we use."

For Thousand, another Southern California-based brand which makes helmets, design is also a priority. "The original concept was [a helmet] you may have found in your grandparents' basement from the '50s or '60s that was just modernized," CEO and founder Gloria Hwang says. "It was supposed to be this retro Steve McQueen look, but feel really modern." Like Retrospec, Thousand's target consumer is the leisure cyclist looking to seamlessly integrate biking not just into their routine, but into their style.  "For people that are using [a bike] to commute around town or are recreationalists that just want to pop to the coffee shop or hang out with a friend, what people really care about in that category is style and convenience." 

For both companies, the pandemic-induced bike craze was good for business. In the last year alone, Hwang says Thousand's business tripled. Khakshouri also noted overwhelming growth, and said it's shown no signs of slowing down. Fashion, thankfully, is similarly rising to the occasion.

While the bike shorts trend of the past few summers can't necessarily be attributed to the growth of bike riding, I've nonetheless witnessed more overt responses from retailers like Urban Outfitters and Free People (which are each owned by URBN); both stock bike baskets as well as frame, seat, and barrel bags from style-centric brands like Mokoyubi and Snack!. For those of us who have retired our skinny jeans in favor of baggier or flared styles, we've luckily been aided by another accidentally convenient trend: Ankle straps

Even as the city reopens, and setting foot in the subway feels just a little less unsafe, bikes are still lining the streets. Just two months ago, New York City's bike share program, CitiBike, broke its daily ride record: More than 106,000 rides were taken around the five boroughs. The previous record was set only last September.

If, like many a novice biker, you're looking for ways to avoid sacrificing your style for a bike ride, I recruited InStyle's fashion editor, Sam Sutton, to break down safe, practical, and, obviously, cute ideas for the many occasions you may be riding to and from. 

And remember: Always wear your helmet!

... to the park.

How to Look Cute on a Bike without Really Trying
Credit: Erin Glover

If the only activity on your agenda is simply riding around in the great outdoors, go for a cute sports bra and bike shorts combo. A pair of fun but sporty badass socks, and a windbreaker just in case round out an easy outfit that's still Instagram-friendly.

Sutton adds, "The goal here was to find a look that provides support and is cool enough for a full, action-packed day, but at the same time, allows you to express yourself and embrace personal style. Instead of opting for simple, solid pieces, go with a playful, printed set." The socks, she adds, an InStyle x Mother Denim collaboration, offer "a dose of motivation."

"The final touch is Free People's voluminous pull-on windbreaker - which can be tied around your waist or packed into a small bag during the day - since it'll surely come in handy as the sun goes down and things cool off," she continues. Don't forget the sunblock!

... to brunch with the gang.

How to Look Cute on a Bike without Really Trying
Credit: Erin Glover

Brunch dates are for capital-F Fashion, and an easy way to showcase your style on a hot summer day is a matching set. They're fun, on-trend, and, best of all, they don't require an hour-length session of "does this top go with these bottoms" in front of the mirror.

"What I love most about this set in particular is that it includes two big trends for summer: knit shorts and shests (styling a vest as a shirt - a top model-approved fashion move)," adds Sutton. "Since it's such a casual bike outing, some everyday sneakers, like checkered Vans, will do, and when styled with tube socks, this laid-back look is complete."

... to work.

How to Look Cute on a Bike without Really Trying
Credit: Erin Glover

A commute to work outfit may be the most high-stakes (no one wants to sit in a sweaty button down for eight hours), but it doesn't have to be the most complicated. Invest in a barrel bag that attaches to the front of your handle bars and converts into a satchel you won't feel embarrassed carrying into the office. Sleeveless ensembles are a great option, too, but if you're truly worried about sweat, pack a separate top to change into.

"What I worried about most here was an outfit that would be cool enough for riding in the summer heat, but also feel professional enough for an office setting," notes Sutton. "Instead of opting for a traditional button-down and blazer combo, I traded them in for summer alternatives: a sleeveless collared shirt and a structured vest (you can always stuff a light, emergency layer in your bike bag or leave a sweater at your desk). Aside from the pants' ankle straps being functional for riding, they're also a big trend for 2021 and a quick way to crop your pants instead of rolling or cuffing."

And for when you arrive, be sure to have a can of dry shampoo (a pro-tip from helmet guru Hwang) on hand to zhuzh up your style and sop up any residual hairline sweat.

... to a date.

How to Look Cute on a Bike without Really Trying
Credit: Erin Glover

If brunch is for demonstrating that you're a very cool fashion girl, then date night is for that, plus some added sex appeal.

"This outfit is definitely on the classic side, but it also proves that with a few key twists, you can really make these staples into something special," says Sutton. "For starters, pulling your button-down off the shoulders (or, alternatively, wearing it backwards or playing around with knotting) make its feel a bit sexier, while the pop of a blue bra and layered necklaces adds a bit of spice. Plus, just because a shoe is comfy and functional doesn't mean you have to sacrifice style. Aerosoles sells a bunch of cushioned, chunky sandals that come in fun colors and prints, giving us the best of both worlds."

Photography and production by Erin Glover. Styling by Samantha Sutton.