Going into fall, I’ve made it my mission to bike as much as humanly possible. During the summer, my trusty red steed has taken me to park hangs and on grocery-store runs, to the gym and to friends’ houses, and to most of my evening activities: dates, parties, late-night karaoke. It’s for these nightly occurrences that my preferred mode of transportation has begun to present a problem. In the daytime, my usual sneakers suffice for nearly every outfit I wear. But when I’m going out in a silky dress or an all-black ensemble, they tend to ruin the vibe. Every time, I’ll try on strappy heels, slim ballet flats, chic leather slides — shoes that go with my fancier outfit — and every time, I end up taking them off and opting for sneakers instead. I’ve even had nights where I changed my clothes after realizing I couldn’t wear the shoes that worked best with my outfit.
Don’t get me wrong, I love my sneakers, but I can’t live like this anymore. I refuse! So I decided to go on a hunt for shoes that are both stylish and comfortable for biking in. I tried 15 pairs of shoes, and here are the eight best I found.
Meu Sol
I love Ipanema flip-flops, so when looking for a more casual but still dressy sandal to try out, I landed on the Meu Sol style — which happens to be from the brand’s Shakira collection. They were a little loose on me, but they were so grippy on my bike pedals that it wasn’t a big deal, and I still had a pretty comfortable bike ride in them.
Kobarah
These shoes are basically sexy Crocs. And if I was biking around the neighborhood in my off-brand Crocs at age 9, I can bike in these puppies at 28. They are legitimately comfortable, which makes them great for a night out, and they have a unique look that commands attention. While biking in them, I did have to be careful not to position my heel too far down while coasting so the heel didn’t skid on the concrete — but they stayed on securely the entire time.
Racer Slingback
This was the biggest surprise of the bunch — I thought with their relatively thin soles, these kitten heels wouldn’t ride super well, but I was wrong! They didn’t slide around on the pedals at all, and the heels were low enough that they never hit the ground as I was pedaling. I felt totally comfortable biking in these.
KINETIC™ Impact Slingback Heel Women’s Sandal
A chunky sandal is probably the best going-out shoe to bike in, which is why I tested several. The height of a platform sandal feels protective, like kneepads for the soles of your feet. This Sorel pair was the cutest one I tried, and although the funky shape of the soles wasn’t built for biking, these still felt quite secure even when I got caught in a downpour on my way to a date.
Edith 2 Penny Loafer
Not a typical going-out shoe, I know, but I love to pair a simple loafer with frilly socks and shorts or a skirt when going out for something like a dinner with friends or a chill movie night. These penny loafers are super comfortable to bike in, especially because the short heel makes them feel extra secure on the pedals.
Ula
No surprise here — these chunky sandals were great to bike in, even though the smooth footbed was a little slippery on my actual feet. Still, the rubbery soles were locked into position on the pedals, and the thick straps on the sandals kept me pedaling steadily.
The Annie
I grew up in Nashville, so when cowboy boots started to become a cool shoe to wear to the club, I was thrilled. But I’ve also realized, through this footwear hunt, that they are the perfect going-out shoe to bike in. The smooth soles you typically find on a pair of cowboy boots aren’t the grippiest, obviously — but because the heels are slanted forward, once you start biking, they hold onto the pedals so securely it almost feels like being clipped in. This particular pair rode very smoothly and showed no signs of damage at the end of my ride, even though they’re made of white leather. Because it was a hot day when I embarked, I did experience a mild amount of calf sweating, but it wasn’t to a concerning degree.
Savannah
I love cowboy boots so much, I had to try two pairs. The Lucchese pair I wore were extremely comfortable from the moment I put them on, and because they were a bit of a tighter fit thanks to the personalized sizing, they felt incredibly secure on the ride to my neighborhood block party (they make good dancing shoes, too). It makes sense; if you can wear them to ride a horse, of course you can wear them to ride a bike, too.
