Highsnobiety

Few wardrobes are as exciting and downright fun to follow as that of Tyler, the Creator. The enigmatic rapper broke onto the scene in the early '00s, surrounded by fellow Odd Future members who all made a splash with their refreshing and subversive take on skate style.

Since the days of Supreme everything, the world of hip hop and fashion has followed every evolution of Tyler’s style which has become one of the more rounded, all-encompassing repertoires in LA and beyond. But, while his wardrobe has progressed to welcome nail artloafers, and even Ushanka hats, his looks remain rooted in casual skatewear — a category in which shorts are king.

Tyler's unmatched irreverence and confident outspokenness in personality translate into 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.

For Sweater Vest Season

Bringing the sweater vest back from hibernation after the 70s has been a multipronged mission in which Tyler played a central role, the Californian artist being one of the biggest advocates of the style. This look from the BET awards proves how the spring knitwear pairs perfectly with shorts, letting the sleeveless vest do the talking while a pair of staple black shorts keep you cool.

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Our LegacyKnitted Cotton Vest
$285
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Dries Van NotenPooles Shorts
$400
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Jil SanderVest
$540
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Acne StudiosRinga Cotton Mix Twill Shorts
$213
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When Cycling

Tyler has a love for cycling that's been well-documented throughout his career. A cartoon T was atop a bike on the over for his Wolf album, he appeared on Frank Ocean's Biking with Jay Z, and he's often seen trying to nail tricks around LA, sometimes with Pharrell. When he's doing that, he usually keeps it simple. No one wants to wear pants when cycling and the rest of the fit should be as care-free.

Y-3Logo T-Shirt
$125
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Gramicci x HighsnobietyHS Sports Shell Packable Shorts
$95
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Golf Wang x ConverseChuck 70
$135
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With a Puffer Jacket

Tyler's disregard for seasonal dressing has led to him bringing together two staples from contrasting seasons: puffer jackets and shorts. However, because it's Tyler, he makes it work. I mean, who else could combine a shirt and tie, ushanka hat, puffer jacket, shorts, and loafers in the same outfit and make it look this good?

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Acne StudiosDown Puffer Jacket
$980
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JacquemusLe Short Giardino
$630
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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 black shorts, in soft cotton twill, offer the perfect mid-ground between bold colors up top and smart loafers below.

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Acne StudiosV-Neck Cardigan Sweater
$510
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and wanderTrek Shorts
$275
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Jil SanderRib Knit Cardigan
$945
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Carhartt WIPFlint Short
$45
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Dr. MartensAdrian
$245
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Want to keep browsing? Head to the Highsnobiety Shop for more products that we love. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

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