Few wardrobes are as exciting and downright fun to follow as that of Tyler, the Creator. The enigmatic rapper broke onto the scene surrounded by fellow Odd Future members who all made a splash with their bold, refreshing take on skate style in the early '00s. Since the days of Supreme everything, the world of hip hop and fashion has followed every evolution of Tyler’s style which has now become one of the more rounded, all-encompassing repertoires in Los Angeles and beyond. But, while the specific pieces have changed, Tyler's overarching style remains anchored in skate style.

What has always stood out most about Tyler, the Creator’s style is the man behind the clothes. Unmatched irreverence and confident outspokenness in personality translate in looks that obey very few ‘fashion rules.' They’re a mishmash of references, subcultures, prints, and colors that are difficult, if not impossible, to recreate. Nowhere is this perhaps more evident than in the way he can style and pull off shorts — a truly divisive area of menswear — like few others.

We took a look through the archives at some of Tyler’s best outfits with shorts to provide some inspiration for the summer months.

With Knitwear

This outfit exemplifies Tyler's fearlessness to try new things. A preppy schoolboy-inspired look is epitomized by high socks and a disheveled tie peeping from the top of a V-neck sweater. The beige shorts, complete with soft pleats, offer the perfect mid-ground between bold colors up top and a black-on-white combo below.

Perfect Prep

Off-Duty Style

Tyler's no stranger to a pair of relaxed-cut canvas work pants, so it follows that a pair of hard-wearing canvas shorts are just as obvious a choice for him. In tandem with an airy Cuban collar shirt, this pair of casual, beaten shorts provides the perfect balancing act to multi-colored leather loafers.

Canvas Cutoffs

Matching Colors

A pair of bright red shorts are sure to make an impact regardless of what you style them with, but when you double the punch with a matching shirt, it's a memorable look. Take notes from Tyler: only sections of the shirt match the shorts — a full match is sometimes a touch too much color to handle.

Color Co-Ord

Shorts and Sandals

Dads the world over have known it for decades, but it's only in the past few years that we've all taken notice: shorts and sandals work. Tyler provides ample proof that simple black-on-black shorts and sandals duet leaves little desire for anything more elaborate. It's simple, sunshine styling at its best.

Summer Stylee

Highlight Pieces

It takes some confidence to pull it off, but if you've got it then flaunt it. Tyler's highlighter-yellow shorts are hard to miss, especially when paired with an actual high-visibility vest. You can't miss it and you won't forget it which, for a man famed for provocative lyrics and even supposedly inciting riots, is mission accomplished.


Our designated Selects section features products that we love and want to share with you. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

What To Read Next