Highsnobiety

This article was published on September 8, 2022, and updated on January 11, 2023

Much has been written about Tyler the Creator's mastery of effortless preppy style, his impeccable wardrobe, and excellent accessorizing (killer watches! Flex-worthy bags!). It's a hard act to follow, so all the more impressive that Tyler's dating one of the few people whose taste can compare to his own.

Tyler the Creator's girlfriend is Reign Judge, an IMG model who's starred in recent campaigns for fashion brands like Miu Miu, Batsheva, Gucci, and Tyler's own GOLF LE FLEUR*.

Note that Judge is 10 years his junior — Tyler is 31, Judge is 21 — but they've been dating since 2021, making their first public appearance together on LACMA's red carpet gala in December of that year.

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Reign Judge is a native New Yorker who's been little-known outside of the modeling realm aside from her relationship with Tyler.

If you want to better know her, peruse Judge's Instagram page, where she reposts her musical idols and uploads stylish selfies blending thrifted cardigans and striped shirts with Chanel bags, a high-low mix complementary to Tyler's too-cool-to-thrift closet.

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Tyler and Judge made a rare public appearance together in New York on September 7, 2022 prior to attending a Lupe Fiasco concert, sitting and strolling around Soho amidst some pleasant late summer weather.

It was indeed pretty nice considering that the typically nasty humidity broke in early September but it wasn't exactly sweater weather outside. Still, you wouldn't know it from the stylish duo.

For his part, Tyler rocked a elbow-patched pink sweater, demonstrating how doable it is to layer a V-neck knit atop a crew-neck T-shirt. It's harder to nail that unstressed professorial vibe than you may think — one corduroy blazer gone amiss and you're Gabe Kotter (look it up, kids).

Tyler's thin-rim sunglasses, washed-out denim jeans, and tassled loafers — his signature shoe — reiterated the retro cool feel that only Tyler so organically channels every time he steps out in public.

Tyler also pulled off a trick that only he has truly dialed down to an effortless science.

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Look again at the individual pieces in his 'fit: they all appear to be thriftable, in the sense that they're pretty conventional, except that everything is thoughtfully styled to create a flattering, relaxed silhouette before getting amped up by Tyler's typically exquisite accessories. Whether his clothes are secondhand or not, the actual fit is intentionally perfect and that makes all the difference.

Special shout-out to Tyler's crossbody Goyard trunk — not only is it a particularly cool low-key luxury flex, but it also serves as a quiet reminder of Tyler's affinity for luggage-style bags over the shoulder bags and totes most other folks prefer as their daily driver.

Reign Judge, meanwhile, wore a neat analog to Tyler's Cool Grandpa look.

She elevated her understated rugby shirt and white slacks with some bougie bits, including her signature Gucci heels, a furry tote, and delicate earrings (with a scrunchie to match!).

The end result is an air of effortlessly cool Parisian elegance akin to the GOLF LE FLEUR* campaign that Judge starred in last year.

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Together, Tyler and Judge are quite a pair. They're a stylistic match more in tune than most other famous pairs, save for someone like Tyler's pal A$AP Rocky and Rihanna.

Neither has been very public about their quite low-key relationship but at least we're able to savor their excellent couple's outfits whenever we actually get them.

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