Highsnobiety

It's been a big few years for Tyler, The Creator. Between the multiple Grammy awards, film scores, and consistent drops from his brand, the musician and multi-hyphenate creative has established himself as a sartorial force to be reckoned with.

Having entered the scene as a high-energy, brightly-dressed skater, his transition into wearing more formalwear such as cardigans, loafers, and oxford shirts was well charted. Now, in 2023, it has aged like fine wine as streetwear's preppy obsession is as big as ever.

And while many of us are playing catch-up on his cool grandpa look, Tyler has been adding more strings to his stylistic bow.

Your Highsnobiety privacy settings have blocked this Instagram post.

Never one to be held back by conventions, the 31-year-old has been building on his signature style with eye-catching combinations such as shorts and puffer jackets, taking his love of luggage to new levels, and giving everyone a lesson in how to wear leather.

And with an equally-fashionable girlfriend by his side, it comes as no surprise that he had to be featured as one of our picks for the most stylish people of 2022.

Your Highsnobiety privacy settings have blocked this Instagram post.

Trying to pick favorites from his countless on-point 'fits is no easy feat but we've given it a go below.

Scroll Down For Our Favorite Tyler, The Creator Outfits

Your Highsnobiety privacy settings have blocked this Instagram post.

While it's a style that will never truly go out of fashion, we have recently been seeing long coats more than ever. Tyler is a perfect source of inspiration when debating how to wear a long mac like the one shown above — and so is his girlfriend Reign Judge.

Shop The Look

Contrast Mac Jacket

$147

Highsnobiety

Buy at Highsnobiety
Image on Highsnobiety

Shaggy Dog Cardigan

$285

J. Press x Highsnobiety

Buy at Highsnobiety

Greyhound T-Shirt

$70

Trussardi

Buy at Highsnobiety

Classic Woven Trouser

$520

Jean Paul Gaultier

Buy at Highsnobiety

When we said his outfits have aged like fine wine, we weren't lying. It's coming up to the four-year anniversary of this look and it should be on everyone's moldboard for smart spring/summer outfits.

Shop The Look

Image on Highsnobiety

Script Bucket Hat

$30

Carhartt WIP

Buy at Highsnobiety
Image on Highsnobiety

Shaggy Dog Solid Sweater

$265

J. Press x Highsnobiety

Buy at Highsnobiety

Striped Dress Shirt

$110

Highsnobiety

Buy at Highsnobiety
Image on Highsnobiety

Turenne Shorts

$159

Sir.

Buy at ssense
Image on Highsnobiety

Polley Shoes

$140

Dr. Martens

Buy at Dr. Martens

Has anyone else been noticing an uptick in the number of leather jackets being worn recently? Drake, Kylie Jenner, A$AP Rocky... they've all been making headlines for their leather jacket styling in recent months and Tyler is giving them all some tough competition with this look.

Shop The Look

Image on Highsnobiety

Logo Cap

$60

J. Press x '47 x Highsnobiety

Buy at Highsnobiety
Image on Highsnobiety

Rego Biker Jacket

$327

Diesel

Buy at Highsnobiety
Image on Highsnobiety

Minaudière Trunk Bag

TBA

Goyard

Buy at Goyard
Image on Highsnobiety

Crinkled Sailor Trouser

$350

Our Legacy

Buy at Highsnobiety

Jeans and a jumper could be described as most people's go-to daily look but, of course, Tyler's version is perfectly elevated. From the matching green Goyard bag and le FLEUR* cap to the festive pink print on the jumper, it's an effortlessly top-tier 'fit.

Shop The Look

Image on Highsnobiety

Peached Nylon Ball Cap

$50

Highsnobiety

Buy at Highsnobiety
Image on Highsnobiety

Chain Link Necklace

$455

Jil Sander

Buy at Highsnobiety
Image on Highsnobiety

Fair Isle Wool-Blend Sweater

$280

Polo Ralph Lauren

Buy at Ralph Lauren
Image on Highsnobiety

Goyardine Grand Hotel Trunk Bag

$4560

Goyard

Buy at Fashion Phile
Image on Highsnobiety

Rad Rufus Straight-Leg Jeans

$200

Nudie Jeans

Buy at Mr Porter

On a practical level, combining shorts and a puffer jacket makes little sense but for some reason, I want to try it out every time I see Tyler do it. The musician wears shorts better than most and this combination is proof that he has mastered the art of getting your knees out.

Shop The Look

Image on Highsnobiety

CMDN

$93

Oakley

Buy at Highsnobiety
Image on Highsnobiety

Shiny Down Jacket

$833

ROA

Buy at Highsnobiety
Image on Highsnobiety

Leopard-Print Shirt

$946

mastermind WORLD

Buy at Farfetch
Image on Highsnobiety

Tailored Shorts

$128

Carlota Barrera

Buy at ssense
Image on Highsnobiety

Penton Bex Quilon Leather Loafers

$168

Dr. Martens

Buy at Highsnobiety
Your Highsnobiety privacy settings have blocked this Instagram post.

An outfit that your Grandad could only dream of pulling off, Tyler puts his own spin on preppy styles with his signature Ushunka hat and some seriously large pearls. Going from shorts and puffer jackets to this is proof of Tyler's range — if you ever needed it.

Shop The Look

Image on Highsnobiety

Shearling Trapper Hat

$550

Pologeorgis

Buy at bergdorf goodman
Image on Highsnobiety

Classic Freshwater Pearl Chain

$368

Hatton Labs

Buy at Highsnobiety

Crinkle Nylon Mac

$147

Highsnobiety

Buy at Highsnobiety

Thermal Crew

$90

Highsnobiety

Buy at Highsnobiety

Heavy Wool Dress Pants

$155

Highsnobiety

Buy at Highsnobiety

Doubling up on a single brand and still keeping to your personal style can be tricky, but Tyler manages it here — wearing a jacket and shoes from Louis Vuitton and Human Made's collaborative line. And while on the topic of things that are hard to style right, there are not many people who could make an all-brown 'fit look this good.

Shop The Look

Image on Highsnobiety

Faux Fur Trapper Hat

$95

Kangol

Buy at Luisaviaroma
Image on Highsnobiety

Leather Jacket With Tiger Patches

$6950

Louis Vuitton x Nigo

Buy at StockX

Alpaca Cardigan

$165

Highsnobiety

Buy at Highsnobiety
Image on Highsnobiety

London Square Bag

from $1395

GOLF le FLEUR*

(Available at 2 Merchants)
(Available at 2 Merchants)

‘70s Cut Wool Trouser

$258

Our Legacy

Buy at Highsnobiety

Want to keep browsing? Download the Highsnobiety app for all the hottest products and brands from the Highsnobiety Shop. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

We Recommend
  • Image on Highsnobiety
    Ungatekeeping The Best Hip-Hop Producers You Should Know About In 2024
    • Street Style
  • Tyler the Creator & a woman out on a date in December 2023, wearing a fur trapper hat and Louis Vuitton jacket
    Does Tyler The Creator Loan His Louis Vuitton Jackets to Just Anyone?
    • Culture
  • cartier crash gold watch
    So, this Cartier Watch Might Set You Back $1.6 Million
    • Style
  • Tyler the Creator wears a green hat, puffy vest, grey hoodie and sweatpants with hiking boots at a WME red carpet event in Los Angeles in November 2023
    Only Tyler, the Creator Could Pull Off Red Carpet-Level Sweatpants 
    • Style
  • Tyler, the Creator's le FLEUR* and Lacoste are back with a Fall/Winter 2023 collaboration.
    le FLEUR*'s New Lacoste Collab Is Retro AF
    • Style
  • Image on Highsnobiety
What To Read Next
  • spring fragrances
    A New Spring Fragrance Is the Ultimate Flex
    • Beauty
  • Models wear Hed Mayner's Spring/Summer 2024 collection
    Hed Mayner's Reebok Collabs Are Too Good to Last Forever
    • Style
  • City Girls' JT attends Diesel's Fall/Winter 2024 runway show in Milan
    City Girls' JT Did Diesel, McDonald's Wings & a Symphony With Solange
    • Style
  • nike zoom vomero 5 design by japan
    No Notes, Nike's Japan-Designed Vomero Sneaker Is Stunning
    • Sneakers
  • adidas samba made in italy
    This $300 Samba Says "Ciao"
    • Sneakers
  • Union Los Angeles' Spring 2024 clothing collection
    Union LA's Chris Gibbs Is Proud to Be a Streetwear Brand
    • Style
*If you submitted your e-mail address and placed an order, we may use your e-mail address to inform you regularly about similar products without prior explicit consent. You can object to the use of your e-mail address for this purpose at any time without incurring any costs other than the transmission costs according to the basic tariffs. Each newsletter contains an unsubscribe link. Alternatively, you can object to receiving the newsletter at any time by sending an e-mail to info@highsnobiety.com

Web Accessibility Statement

Titel Media GmbH (Highsnobiety), is committed to facilitating and improving the accessibility and usability of its Website, www.highsnobiety.com. Titel Media GmbH strives to ensure that its Website services and content are accessible to persons with disabilities including users of screen reader technology. To accomplish this, Titel Media GmbH tests, remediates and maintains the Website in-line with the Web Content Accessibility Guidelines (WCAG), which also bring the Website into conformance with the Americans with Disabilities Act of 1990.

Disclaimer

Please be aware that our efforts to maintain accessibility and usability are ongoing. While we strive to make the Website as accessible as possible some issues can be encountered by different assistive technology as the range of assistive technology is wide and varied.

Contact Us

If, at any time, you have specific questions or concerns about the accessibility of any particular webpage on this Website, please contact us at accessibility@highsnobiety.com, +49 (0)30 235 908 500. If you do encounter an accessibility issue, please be sure to specify the web page and nature of the issue in your email and/or phone call, and we will make all reasonable efforts to make that page or the information contained therein accessible for you.