(Courtesy of Highsnobriety)


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 currently dating one of the only 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, Gucci, and Tyler's own GOLF LE FLEUR* brand.

Note that Judge is over 10 years his junior — Tyler is 31, Judge is 20 — but they've been dating since last year, making their first public appearance together on LACMA's red carpet gala in December 2021.

I'll reserve judgment on the decade separating their ages since we're just here to talk clothes and, in that regard, Judge's outfits are a neat match to Tyler's own smart-casual style.

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

It was pretty nice considering that it's only early September but it wasn't exactly sweater weather outside, though you wouldn't know it from the stylish duo.


Indeed, 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 sounds easy but it's hard to nail that unstressed professorial vibe like Tyler.

His thin-rim sunglasses, washed-out denim jeans, and tassled loafers — Tyler's signature shoe — reiterated the retro cool feel that Tyler so organically channels.

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

Look at the individual pieces in his 'fit: they all appear to be thriftable in their branding-free appearance, except that everything is thoughtfully styled to create a flattering, relaxed silhouette before getting amped up by exquisite accessories that include a chunky necklace, thick rings, and crossbody Goyard trunk.

The latter, in particular, is particularly cool as a low-key luxury flex. It also serves as a quiet reminder of his affinity for luggage-style bags.

Reign Judge, meanwhile, was wearing a worthy counterpart to Tyler's Cool Grandpa look, with the casual feel of a rugby shirt and white slacks elevated by Gucci heels, a furry tote, and delicate earrings with a scrunchie to match.

She gracefully attains an air effortlessly cool Parisian elegance akin to that GOLF LE FLEUR* campaign she starred in last year.

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

But they've got their own taste and a unique approach to dressing that's simultaneously worldly and youthful. Couple goals, indeed.

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