Like a messenger running 30 minutes late on a fixie, the bike shorts trend shows no signs of braking anytime soon. I can certainly see why it has such staying power, the garment, which has been seen everywhere from Chanel to Off-White, offers nostalgic ties to Princess Diana to the kind of comfort not many items of clothing can surpass. They also give lots of opportunities to play with proportions, as the perfect counterpart to baggy sweatshirts and structured blazers alike.

And yet. And yet! I haven’t quite figured out how to wear them. I’m no stranger to experimental style, nor am I afraid of risk when it comes to concocting outfits, but for some reason the secret to incorporating bike shorts in a way that doesn’t feel too “Jane Fonda in the 80s” or too “Kim Kardashian on Instagram” eludes me. I don’t mind sitting out a trend, but I have a vested interest in giving one a go (see: Princess Diana, unparalleled comfort, etc.), so I tapped an expert for assistance.

Lillian Ahenkan, a.k.a. Flex Mami, a.k.a. a DJ, author, MTV Australia host and all-around cool person, is definitely an expert when it comes to styling bike shorts with consistently fresh results. Having admired her approach many, many times, I had no doubt she would be in possession of some helpful tips. Scroll down to read what they are (and see them in action).


1. Lean Preppy

If the word “preppy” conjures images of a pink and green color palette, cardigans, and headbands, then a pair of black bike shorts might seem like the epitome of its stylistic foil. Therein lies the magic of combining them. Intermixed with the aforementioned elements of prep, the stereotypical identity of bike shorts is thrown just enough out of balance to feel surprising. “This look is an homage to me dropping out of uni multiple times,” Lillian told me.

See All 8

2. Keep Your Contrast Up Top

Pairing bike shorts with a blazer and strappy high-heels has been done enough (on runways and Instagram alike) to make the obvious contrast of glamour and athleticism feel…well…obvious. Circumvent this cliché by wearing a simple, structured top that isn’t overtly intended for a night on the town, and slipping on your favorite pair of errand-running sneakers. If you have the urge to sprinkle in a beaded bag that would feel equally at home in a bar or on your best friend’s couch, Lillian is all for it.

See All 5

3. Think Pink

Pretty Little Thing bike shorts, ASOS blazer — similar here, Jaggar shoes, Staud bag, custom Playboy necklace — another here

Bike shorts often appear in minimalist, monochrome looks, which is why I mentally associate them with colors like cream, black, and–on a wild occasion–olive green. Lillian suggests shaking up this connotation by embracing a more saturated look. Pink is a great option, especially since it’s typically reserved for frilly dresses and midi skirts and other things that are very much not in the same style family as bike shorts. “This is what Elle Woods would wear if Legally Blonde came out in 2019,” Lillian told me. I couldn’t have put it better myself.

See All 5

What do you think of the bike shorts trend? If you’re a fan, how do you wear them? Would love to hear your thoughts in the comments.

Photos provided by @flex.mami.

Man Repeller editors endorse products we genuinely love. If you end up buying something through our links, we may earn an affiliate commission. Learn more here.

Get more Fashion ?