How to Master Bicycle Chic in 3 Easy Steps


Admittedly, this post was scheduled on my editorial calendar for the middle of June but breaking a foot can really eff up your blog schedule more than expected. Fine, truth be told I’ve never once actually published a blog post on the day I had it scheduled (don’t tell my blog coach! ) so I’m not quite sure why I’m blaming my foot. I guess it’s just a lot easier to blame my inability to meet deadlines on that, rather than my episodes of depression, delusion from lack of sleep, and poor time management skills. Fine, my time management skills are actually okay if I really really need them to be. I just choose to ignore the clock and lay on the floor talking to my dog instead. It’s much better that way. #SorryNotSorry

Anywayyysss… Growing up in South Florida, I never really had the desire to master the bicycle chic look. Mostly because there is literally no way to look chic as you melt off your bike in the 95 degree, 100% humidity weather. Sorry Florida people… Maybe skip this post and come back on Thursday because I don’t know how helpful this one will be to you. My editorial calendar says we’ll be talking about slip on sneakers but I’ll probably find something else to ramble about around 4am Wednesday morning. Just kidding… STAAYYY PLEASE DON’T LEAVE! 

If you don’t know how to ride a bike (or if you’re not very good), just move to Aspen

Aspen is a really magical place. It’s basically the dreamland for all bicycle chic bike riders which is what inspired this post. Being the 3rd US city to use 100% renewable energy, Aspen is all about the #GreenLife. On the road, precedence is given to pedestrians and cyclists as an incentive to not drive cars. There are even roads that are specifically for cyclists and pedestrians – cars can only drive one block on those roads. That and they hiked up parking rates in the downtown core and the parking garage to get people to use alternative methods of transportation. Yes, THE parking garage. There is only one parking garage in the city of Aspen. I was totally culture shocked by that one.

My boyfriend was managing a 100% electric free transportation service down in Florida. The city of Aspen decided to subsidize a branch, which is how he ended up out here. Personally, I’ve never been a beach girl as sand likes to linger in cracks I did not even know existed for amounts of times I should not admit here publicly. So needless to say, I was pretty stoked to trade in my beach view for a mountain view. But what REALLY got me? EVERYONE rides bikes here and cars HAVE to look out for you and give you the right of way so even though I’m a spazz and relatively uncoordinated there’s a good chance that the cars are already looking out for some idiot on a bike who doesn’t know how to ride with one hand which means she can’t use the other as a turn signal. Perfect.

I don’t know about you but I’ve definitely had the bicycle chic day dream on more than one occasion.

It’s a beautiful Saturday morning so I decide to ride my bike into town for a cup of coffee at my favorite coffee shop with my favorite mountain view. I put my pup in the basket (she’s 50lbs so good luck with that one, daydream Michelle) of my pastel purple cruiser (I don’t actually own one of those – or a bike at all – just to clarify) and make my way into town. **Also worth noting, there’s definitely a bouquet of flowers in the basket. Obvs…** Anyway, the sun is shining bright and I’m glistening, not sweating. As I finally catch some speed on that last downhill stretch into town, I stop pedaling, close my eyes, and feel the wind through my hair as my sundress is magically floating behind me. 

And then all of a sudden the wind changes direction and my hair is all in my eyes. My sundress gets caught in the chain of my bicycle which causes it to suddenly jerk and stop short. My pup goes flying out of the basket and into moving traffic. I am laying on the ground flashing the park ranger who happened riding by. And I look up to like 30 cars that are stopped and starring at me, making sure they didn’t just witness a death by sundress in bike scenario. But don’t worry… the flowers are totally fine.

None of this has actually happened to me IRL but it’s 100% a fear of mine which is why I think mastering the bicycle chic look is imperative to your ego, confidence, and safety!

How to Master Bicycle Chic


Some people will say you can totally wear heels when you are trying to be cycle chic but I say don’t push your luck. Personally, I am obsessed with the sneaker/girly outfit look which is pretty perfect for riding a bike. Also, I have a phobia when it comes to wearing sandals so there’s that. Supergas are my go-to sneakers and I think everyone should have like 10 pairs a pair.

When you are choosing the shoe for your cycle chic look, pick a shoe you are really comfortable in. If a deer hops out in front of you and you have to stop short or suddenly put your foot down, think about the shoe you want to be wearing when that happens. I can almost guarantee it’s not gonna be your strappy Steve Madden heels. Also, sorry if the deer scenario doesn’t quite work for you. It’s become a bit of a norm around here.


I’m gonna skip over the obvious jeans shorts and a cute top scenario and dive right into the dresses. Okay, so you remember how in high school you couldn’t wear your dresses shorter than your finger tips? Or maybe it was mid thigh? I think it was finger tips? I dunno, TBH I blocked most of those years out but let’s just say finger tips for the sake of this example.

So I recommend wearing a dress that is a finger’s length longer than your finger tips. It’s like kind of the perfect length to keep your dress securely tucked under your butt cheeks, basically up your butt crack, while you are riding (see 4th picture down). If you can keep your dress securely under your tush, and wear a cross body bag over your lap, you won’t have to worry about flashing everyone around you. I think midi skirts/dresses are awesome for bike rides too. All you have to do it tie the extra fabric in a knot over your lap during the ride. Believe it or not, rompers can be just as questionable as some dresses so I recommend going for a quick ride around the block before actually committing to an outfit and heading out for the day.


I almost always wear a neckerchief when I’m going for bicycle chic. A) It’s super chic. B) If your hair gets all crazy you can take it off your neck and use it as a head scarf. Win-win. I also think cross body bags are the way to go as you can basically use them as a paper weight for your outfit. I guess that makes it an outfit weight if we’re getting technical? And then from there just add whatever jewelry you’d normally wear to accessorize your outfit.

And there ya have it! Three easy steps to bicycle chic!

What’s your favorite outfit for a bike ride? Let me know in the comments below!

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