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The Most Decadent (and Depraved) Thing at the Kentucky Derby Should Be Your Fits

Doing drugs isn't cool. You know what's cool? Dressing like you do.

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White, Footwear, Clothing, Peach, Boot, Fashion, Pink, Riding boot, Shoe, Illustration,

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Everything I know about the Kentucky Derby I learned from reading Hunter S. Thompson's fucking bonkers account of his experience at the sporting event in the '70s. You guys ever read that shit about his standard day-to-day drug regimen? The man was a self-medicating machine. If you want to make drugs less appealing, why on earth would you continue to green-light endlessly entertaining pieces of narrative non-fiction in which the writer's prolific drug intake is basically its own character within the story?

Well, it's Derby season, baby. Dress the part and you, too, can look like the type of guy that could conceivably invent an entirely new style of writing while on enough drugs to sedate an elephant. Let's get weird.

Odyssee Ivory Monroe Unstructured Double-Breasted Striped Hopsack Suit Jacket

Ivory Monroe Unstructured Double-Breasted Striped Hopsack Suit Jacket

Odyssee Ivory Monroe Unstructured Double-Breasted Striped Hopsack Suit Jacket

Now 80% Off
$229 at MR PORTER

If you're going to lean into the outlandish suiting element that remains a perennial staple of derby style, do it wearing something you'll actually want to rock all summer long. 

Odyssee Ivory Monroe Striped Hopsack Suit Trousers

Ivory Monroe Striped Hopsack Suit Trousers

Odyssee Ivory Monroe Striped Hopsack Suit Trousers

And when the full suit is too big a flex, break the set up and wear the trousers with basically any shirt you already own.

Proper Cloth Performance Stretch Light Blue Prince of Wales Check Shirt

Performance Stretch Light Blue Prince of Wales Check Shirt

Proper Cloth Performance Stretch Light Blue Prince of Wales Check Shirt

Pro tip: as long the patterns in your outfit (in this case, the broader stripes on the suit and the subtle plaid of the shirt) are different scales, feel free to mix and match 'em with impunity. 

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R.M. Williams Classic Chelsea Boot

Classic Chelsea Boot

R.M. Williams Classic Chelsea Boot

An iconic silhouette from an equally iconic OG of the style.

The Tie Bar Textured Solid Knit Root Beer Tie

Textured Solid Knit Root Beer Tie

The Tie Bar Textured Solid Knit Root Beer Tie

A silk knit tie is never, ever a bad idea. 

Warby Parker Hatcher

Warby Parker Hatcher

Warby Parker Hatcher

Warby's going to Warby (i.e., allow you to look like an absolute baller on a decidedly non-baller budget). 

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Champion Terry Bucket Hat

Terry Bucket Hat

Champion Terry Bucket Hat

Very big Hunter S. vibes. 

Nanamica Club Double-Breasted Tie-Dyed Alphadry Suit Jacket

Club Double-Breasted Tie-Dyed Alphadry Suit Jacket

Nanamica Club Double-Breasted Tie-Dyed Alphadry Suit Jacket

The statement suit you didn't know you needed, done up in one of Nanamica's signature super-functional fabrics. 

Nanamica Easy Wide-Leg Tie-Dyed Alphadry Suit Trousers

Easy Wide-Leg Tie-Dyed Alphadry Suit Trousers

Nanamica Easy Wide-Leg Tie-Dyed Alphadry Suit Trousers

Wear the suit. Don't let the suit wear you. 

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Uniqlo U Cuban Short-Sleeve Shirt

Cuban Short-Sleeve Shirt

Uniqlo U Cuban Short-Sleeve Shirt

Now 63% Off

Yes, I'm going to keep incorporating this shirt into any outfit I can until you cave and buy it out of sheer exasperation. It's that good.  

Uniqlo Socks

Socks

Uniqlo Socks

The best pair of socks I've seen in a minute, from one of the best collaborations available to cop now

Vans Navy OG Classic Slip-On Sneakers

Navy OG Classic Slip-On Sneakers

Vans Navy OG Classic Slip-On Sneakers

Classics are classics, no comment necessary.

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Paul Smith Soho Slim-Fit Wool and Mohair-Blend Suit Jacket

Soho Slim-Fit Wool and Mohair-Blend Suit Jacket

Paul Smith Soho Slim-Fit Wool and Mohair-Blend Suit Jacket

If you're going to insist on committing to the full pastel look, at least do it tastefully.

Paul Smith Soho Slim-Fit Wool and Mohair-Blend Suit Trousers

Soho Slim-Fit Wool and Mohair-Blend Suit Trousers

Paul Smith Soho Slim-Fit Wool and Mohair-Blend Suit Trousers

(Thankfully, "tasteful" is Sir Paul Smith's middle name.)

Topman Navy Stripe Knitted Polo

Navy Stripe Knitted Polo

Topman Navy Stripe Knitted Polo

Allow me to introduce you to your next favorite knit. I'll let you two get acquainted. 

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Nepco Footwear Embossed Entercarne Bit Moc

Embossed Entercarne Bit Moc

Nepco Footwear Embossed Entercarne Bit Moc

Yes, these shoes are almost certainly a hassle to ship to the States. Are they worth all the effort? Take another look at 'em. (In other words: absolutely.) 

Carrera 52mm Round Sunglasses

52mm Round Sunglasses

Carrera 52mm Round Sunglasses

Now 40% Off

Carrera is consistently the source for super-sleek, racing-inspired eyewear that doesn't break the bank. 

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