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RVA Style

Wearing heels while biking and other things super stylish bike commuting women do

Great personal style and commuting on a bike are not mutually exclusive things, according to personal wardrobe stylist Sydney Lester.




Photos: Brian McDaniel

Richmond is home to many women with very distinctive style perspectives who also happen to commute regularly on their bikes. Makeup is applied and hair is coiffed before donning a helmet. Heels replace clip-on cycle shoes. Clothing is comfortable but stylish. Items are tossed in chic back pack and messenger bags or placed in oversized baskets.

Quite frankly, I was intrigued by this rare breed of woman who seemed effortlessly cool, was actively doing her part to create a more sustainable earth, and for whom wearing heels while biking was a natural thing.

In order to explore this idea of super stylish women riding bikes (TV show in the making?), I enlisted my friend Brian to take photos (in film no less!) of four women whom I had long admired for their personal style while biking. Long admired can also stand for gawking every time I saw them bike up in heels, pull off their helmets and shake out their gorgeous hair, but that’s neither here nor there.

My goal with this project was simple: capture a range of women who all have crazy cool, different personal styles, but who also all ride their bikes regularly as their means of transportation. There is not a yoga legging or tennis shoe in sight.

So without further ado, I’d love for you to meet and get to know Anika, Catherine, Tess, and Rebecca. Who knows, you may just be inspired to go buy a bike and don heels while riding.

Anika Horn


Age: 30

Wearing: Nine West heels / H&M pants / Banana Republic top / Osprey backpack.

How do you fill your days? I accelerate startup founders at VCU and Lighthouse Labs, I mentor social entrepreneurs through the Chamber’s THRIVE program and help the community in Virginia’s mission-driven companies grow as B Keeper at Impact Makers.

How long have you been biking and what got you into bikes? Living in a city means riding a bike. In Germany – where I’m from – rush hour takes place in the bike lane; most people bike everywhere so it’s been my main mode of transport for over five years. When I moved to Richmond last year, I bought a bike straight away. I even brought my helmet from Germany.

What kind of bike do you ride? My partner and I both ride Giants. I tried a road bike first but with all of Richmond’s potholes and some pretty fantastic trails I feel much more comfortable on a mountain bike.

So…you look really stylish! Tell me more about your personal style. I love dresses and heels! I have a classic, feminine style, but I love a bit of an edge or unexpected detail thrown in.

Do you REALLY wear that while biking? Absolutely. I bike to work, meetings, events – really anywhere that’s under 7 miles (my schedule usually doesn’t allow for more than 30 minutes from one location to another). As a consequence, I’ll be in that outfit all day. The only exception is when I feel like wearing a dress that is unsuitable for biking. Then I fold it up in my backpack and get changed on-site.

Tell me some of your style and biking secrets. Biking in heels in no harder than biking in trainers. Pay attention when getting on and off your bike, that’s all.

Use a backpack. Nothing is worse than trying to balance uneven weights on your shoulders or over your shoulder. A backpack provides stability and keeps your hands free.

When it’s really hot, I arrive five minutes early at any given meeting. I don’t sweat while I bike (the motion makes for a nice breeze) but when I get off, I sometimes feel a rush of heat and need to cool down. Always have a travel size deodorant and hairspray in your backpack, just in case. 😉

What is it about biking that you love? Biking is me-time. I bike to workouts with X-Team Fitness around town every morning. It allows me to have the city for myself before starting my day, and that’s quality time. Secondly – no offense – but driving in the US when you’re used to German traffic can be aggravating. On my bike, I am flexible and get places just as quickly without traffic anger or parking issues. I am a happier person when I am on my bike.

Catherine Illian


Age: 37

Wearing: Y and H Mercantile dress / Nisolo Mendez flats in cranberry / bracelet from Mexico / necklace received as a gift / gold stud earrings from JCPenney.

How do you fill your days? I am the owner of Richmond Rides Bicycle Tours. You can find me guiding on one of our four tours, creating new tours, and working with our awesome guides.

How long have you been biking and what got you into bikes? I have been biking since I was 7 and learned to ride my banana seat one speed. Three years ago we bought a used trailer and I biked around Church Hill with my three kids in the trailer and a baby seat on the back of a mountain bike. I used it for transportation and fun! We loved that so much we chose to sell our car a few years ago and only have one car now and use lots of different bikes to get around Church Hill and town.

What kind of bike do you ride? I ride a Metrofiets E-assist. This bike is similar to the bakfiets style bikes from the Netherlands, but it is American-made (Portland) with a steel frame so it is really easy to ride. The E-assist allows me to commute with my kids or other gear related to the bike tour company no matter what the distance or the weather.

So…you look really stylish! Tell me more about your personal style. My style is eclectic minimalist. I’m not into have a ton of clothes, but I love every item of clothing in my closet and wear it often. I also hate to shop and so have been known to use online clothing services when I need something. I also love small boutiques where they have a unique style and help you find things that fit your body type and frame.

Do you REALLY wear that while biking? Every time I buy clothing – I think about if I can wear it biking. If I can’t, I don’t buy it. Some of the things I think about include: trending towards relatively slim pants and dresses or skirts that have some extra material so I can have room to modestly pedal. Maxi dresses are great because I just hike them up a bit and pedal away!

Tell me some of your style/bike secrets. I’m not sure I don’t sweat – it’s pretty impossible to walk outside in the humid Richmond summers and not glisten a little. I do wear layers so I can peel them off if I warm up while biking – I like to wear clothes that aren’t too clingy and leave room to breathe.

What is it about biking that you love? I love how when I’m biking, I’m present to my surroundings – it isn’t safe to check my phone, I’m immersed in my surroundings while also getting from A to B. I love being able to chat with my kids while biking to school. I love being aware of my environment. I love being able to stop and talk to people I love that I pass as I’m biking. I love the sense of community that biking enables. I love the human scale of biking. I can never be in too much of a rush when biking.

Tessa McKenzie


Age: 34

Wearing: Latigo lace up heeled sandals / Levi’s jeans / Laser cut faux leather top, Sunday in Brooklyn from Buffalo Exchange in New Orleans / Surface Handmade necklace / Bijules Jewelry ring

How do you fill your days? I spend my days living Richmond. I bike it, walk it, explore it and like to party in it. By being active, I am able to experience and discover all the things that make it such a great place to be. In my work in VCU’s Division of Community Engagement, I focus on developing infrastructure that creates fruitful collaboration and partnerships that enhance the university experience and benefit the Richmond community. I also get freaky on a bike teaching spin classes at BOHO Cycle Studio. Come by and party – Monday nights at 5:30 p.m.!

How long have you been biking and what got you into bikes? I started cycling 10+ years ago while living in Portland, OR. It’s a big deal out there. The biggest reason I go by bike is because it’s “intelligent laziness”. I don’t do it to stay fit or look really sexy in a helmet. I do it because it’s easy and because I am too lazy to drive around looking for parking and then walking from my parking spot to the front door. I’m also too lazy to get stressed out and panic about being late because there’s no parking. So, instead, I bike and usually get there early.

What kind of bike do you ride? I have 2 bikes: 1 for commuting and 1 for road riding.

Giant Via. This bike not only looks slick, it’s extremely functional in the city because of its upright design with front-rack, comfy leather saddle and 3 speeds. It’s a men’s design which I had no idea when I purchased it.

Trek GT. Women’s-specific road bike. This bike is more of an endurance bike and is built to go fast and climb high. It probably weighs less than my helmet. It has drop handlebars and clipless pedals which create a very powerful pedal stroke. The coolest thing about this bike is the bike lights. They are powered by pedaling. Very. Neat. Oh.

So…you look really stylish! Tell me more about your personal style. I’m inspired by the colorful, unusual and bold, so my wardrobe is 1/4 bohemian, 1/4 avant-garde, 1/4 urbanite, and 1/4 black. Every morning I strategize my outfit depending on how active, how long my day is, and what I’m doing. Flats are best for city walking; heels work best for sedentary days and biking (yes, you can bike in heels). My outfits dictate my day, so my strategy is to look your best, feel your best and have a fabulous day. I travel a lot, and one of my favorite things to do is hit up a thrift store in an eclectic/affluent neighborhood. It’s a total time sucker, but I’ve developed a good methodology to finding unique stuff at a reasonable price.

Do you REALLY wear that while biking? For real, I do. You will find me in dresses, high-waisted pencil skirts, heels and jewelry because that’s how I roll off the bike. I generally don’t wear sneakers or change into yoga pants to push the pedals because that would require more work to change in and out of clothes when you get there. Repeat: intelligent laziness. The bicycle is elegant and makes it easy to be a part of a fashion conscious lifestyle.

Tell me some of your style/bike secrets. Dress comfortable as you would off the bike. Just because you go by bike doesn’t mean that you are confined to the “cycling specific” aisle. The secret to this normal clothes idea is that you need the right bike to facilitate it. Think upright, flat pedal, and with a good rack so you take the load off your back and keep it sweat free.

What is it about biking that you love? Cycling bring us together. In a city that has a history of division, a bike ride through the neighborhood can create social connections and change your perspective about the Richmond community. Cycling also feels like freedom. You’re balanced, self-propelled, and decide exactly where you go, how to get there, and how quickly.

Rebecca Thomas


Age: 45

Wearing: Vince shirt / Everlane culottes / Emerson Frey skater shoe / ring made by me at the Visual Arts Center / Rayban sunglasses

How do you fill your days? Walking, biking, reading. I love my home in Jackson Ward, so hanging out there is always a pleasure. Living in Richmond means lots of Virginia Museum of Fine Arts and delicious meals. For work, I check in on my restaurant (kybecca) and am developing a site to begin consulting for other restaurant owners. It’s a tough business and I’ve learned a few things!

How long have you been biking and what got you into bikes? I can’t remember not having a bike. I learned with my Dad at age 6 or 7 and always had some kind of bike after that. Some places I have lived were more conducive to bike riding than others. It’s not accident that I ended up in a bike-crazy city.

What kind of bike do you ride? I ride a Raleigh Cadent. It’s a great all purpose work-horse. I recently schlepped it on a six week camping trip across Florida. It was my adventure partner, wouldn’t have been the same trip without it.

So…you look really stylish! Tell me more about your personal style. I love dressing. I see it as an interplay of appreciating your body, showcasing beauitful things and communicating something about you who are. My style is simple, tailored with an emphasis on great fabrics. I love the menswear for women look. Done well there is hardly anything sexier.

Do you REALLY wear that while biking? It depends on the purpose of the ride. If it is just to get from A to B, then yes, I ride in street clothes. I walk a lot too so my wardrobe is based on multi-function pieces.

Tell me some of your style/bike secrets. My tip for stylish riding is the same for staying active in general. I look for well cut, simple clothes that can be worn for good movement in general. On occasion I love a great dress and high heels, but more often I want to be able to comfortably take a walk or ride my bike. Tailored pieces made from fabrics with a little stretch fit the bill.

What is it about biking that you love? Riding a bike is another version of freedom. It feels good and I love the simplicity of it.


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