Cycling Shorts & How to Style Them

April 18, 2019

Let me introduce you to my latest obsession: cycling shorts. In my teenage years, these were reserved purely for the chicken-legged teenage boys who ran cross country. These days, the Kardashians are wearing them and people are losing their minds. Thankfully, the Kardashians were not the ones to invent this trend, just like they didn't invent big butts, full lips, breathing, etc. However, they did play a large part in reviving and updating the classic cycling short look. A lot of inspiration has been coming from the late Princess Diana. Her go-to casual outfit was a pullover sweatshirt, cycling shorts, tube socks, and athletic shoes. This was the perfect look for Diana, who was often referred to as 'the people's princess' due to her philanthropy and being relatable to her subjects.

While this is the classic way to wear cycling shorts, ways to style them have evolved in 2019. They are not only limited to athleisure, but mixing with band t-shirts and soft blouses creates effortless looks that can transition from day to night. It's also a great way for me to get away with a black-on-black outfit in the summer without dying of heatstroke.


Here I've style 3 outfits with different kinds of cycling shorts. Not going to lie, the first one is inspired by Dena Smith, the Leo Queen behind Leo With Cancer and the creator of the cult beauty favorite, Leo Oil. While these all align with my personal style, each look is very different and can cater to many different kinds of personal style. (Click the photo for deetz) Find the style that works best for you. Play with patterns, texture, layering, and accessories. In fashion, rules are meant to be broken. Nothing is off limits!

I recently acquired my first pair of cycling shorts this past weekend. I styled them with one of my favorite graphic tees and white Adidas to go to a concert in Wynwood, Miami - I was cool, comfortable, and felt very stylish all evening without feeling overdone. This will probably be my go-to look for the summer. I could also get away with it year-round because, well, Florida.

T-Shirt / Pizza Party Printing
Shorts / EleVen by Venus
Sneakers / Adidas
Bag / Rebecca Minkoff / Similar Here

If you are interested in trying out this look and want to know some good places to shop, check out these options. Most fast fashion places like H&M and Target will likely have these, but if you want good quality, sustainable items, I recommend these:

LHLL Store

EleVen by Venus (these have pockets!)

Girlfriend Collective

Outdoor Voices



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