I'm A Fashion Writer Who Bikes Everywhere — & This Is What I Wear

Photo by Sophie Hur.
This post was originally published on July 17th, 2019, when commuting to an office on a daily basis was very much the norm. Even though our lifestyles have changed considerably in 2020, we know that a lot of people are getting around by bike these days. Since our Fashion Market Writer’s bike-style tips are still relevant, we’ve simply updated the products discussed below to ensure that everything is in stock. Enjoy!
Disclaimer! I am not an expert biker. I don’t know how to change a tire; I’ve never touched a “fixie”; I just learned about hand signals, and I am probably still doing them wrong. However, I should probably put my feelings of imposter syndrome aside (said every woman at some point in her life), because, despite these shortcomings, I do ride my bike every single day. Mostly because I am convinced it’s the best way to get around. You burn calories without burning fuel, and if you’re biking in a city, you’re probably getting to your destination faster than anyone stuck on the subway or sitting in traffic. As the fashion market editor here on the Shopping team, I’m here to dispel any notion that you have to sacrifice style (if fashion is something you're passionate about too) if you want to live that cycling life. I wish I had a better reveal here, but the truth is that riding doesn’t affect the way I dress very much. There are things I don’t wear — billowing silk skirts, heels, polyester anything — but for the most part, I dress the way I want and have a few simple hacks and sworn-by pieces to optimize my outfits for safety and practicality.


This list focuses on fashion and is decidedly gear-free, but as a wise woman once told me: it’s not a bike without a helmet. Do not even question the necessity of this life-saving accessory. I actually feel so bad that I am not wearing one in this picture. My current noggin protector is from the brand Thousand, and it’s as good as any. Don’t complain about the cost, either — $89 is a small price to pay for your life. If you’re going to be biking in the city, the best type of helmet — and the one that I have — is a commuter style. They’re more stylish and have less aggressively performance-y bells and whistles, which you don’t really need if you’re not logging 50 miles daily and/or cruising through rocky terrain — and I suspect if you engage in these latter styles of biking, this piece might not be for you. (Although, thank you for reading.) If you need more detail on the different types of helmets, REI has a great primer.

Bike Shorts

Let’s not forget that fashion’s current favorite item has its roots in, um, actual bicycling. The upside of this skintight short’s status as of-the-moment must-have? There are more stylish options that I can count. Woohoo! No more cutting off old tights at the knee to wear underneath skirts as I cycle about. (True story. I am wearing my DIY pair in the photo.) Throw these babies on underneath any skirt or dress, and pro tip: if you’re wearing a fuller volume or a-line style, you can tie it in a knot, or, even more horrifying to bystanders, tuck the bottom of your skirt into your shorts. This might look a little weird, but who cares? No one will notice as you whiz by on your wheelie. (Also, one of the pairs below is more of a basketball short than a bike short. Sorry! I like them so much.)

A Tiny Bag

I was going to speculate that a biking habit helped to streamline my purse contents in order to tote fewer things, but I actually learned that from being older, wiser, and dealing with the frustration that came along with toting around too many things. Nowadays you can find me carrying only the essentials tucked into the smallest crossbody bag I can get away with. Now, you may wonder what happens on the days that larger items are necessary — say, a laptop, lunch, extra shoes, etc. That bring us to ...

A Big Bag (That Can Live Inside The Tiny Bag Until You Need It)

Sometimes, when you’re taking the ol’ velo out for a spin, you acquire things: loaves of bread, button-downs from the $20 rack at your local vintage store, street books, etc. While I’m likely to start the day with only a phone, keys, and wallet credit cards secured with a hair tie stuffed into a teeny-weeny crossbody, I always leave a little room for a packable tote or backpack.

Loose Pants

You might think that tight pants are the way to go when biking, as they stay close to your body and won’t get caught in your vehicle’s gears (a serious danger). And for some, this may be preferable (spandex is the racer’s textile of choice for a reason). However, I find tight pants to be constricting while riding — especially this time of year — and I prefer a good, old fashioned pair of loose or wide-leg trousers, which I simply roll up to the knee when I’m riding. (And I mean way up to the knee — you do not want your loosey-goosey pants getting caught in your gears.) Again, I often look insane, but who cares?

A Waterproof Jacket That Covers Your Butt

It’s a dreaded scenario that every biker knows well: rain! Precipitation makes roads slippery and stirs up all of kind of street juice that will splatter your clothing like spin art. I know that carrying around a jacket during the summer feels like torture, but your white dress will thank you if you have this handy when it starts to drizzle.

Shoes That Stay Put

One might think that biking is only safe when you’re sporting a lace-up, closed-toe shoe that will hug your feet and protect them from the elements. And that’s certainly a great shoe to wear while out riding — you will find me in Vans almost every day. However, I’ve also cycled in sandals, loafers, platforms, and as you can see from this photo, clogs. My takeaway? First, you need to see what feels safe and comfortable for you; and second make sure your shoe has a tight upper or a firm buckle. (I.e., avoid slides at all costs.)
As you can see, I’m not reinventing the wheel (zing?) with any of these suggestions — these are just the pieces that I gravitate towards to ensure that my ride is comfortable, stylish, and safe. If you’re an expert biker or fellow helmeted freewheeler who sees some holes in this list, let me know in the comments — I’m always looking for suggestions.

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