Men’s Kentucky Derby Style: What to Wear for the Most Exciting 2 Minutes in Sports

The first Saturday in May is like Coachella for the horsey set. The Kentucky Derby — at Churchill Downs in Louisville, Kentucky — kicks off spring party season with thundering hooves, sweet mint juleps, and a tradition of colorful, Southern sartorial expression. This year the “Run for the Roses,” is on May 4, followed right on the hooves by the Preakness and Belmont Stakes, rounding out the highly sought-after Triple Crown of racing. 

“The Kentucky Derby provides a great excuse for guys to step outside their comfort zone, pairing up bolder colors of pants and blazers,” says John Ballay, CEO and co-founder of custom clothier Knot Standard (and a fine Southern gentleman by birth, himself).

“My goal and advice is always to pair up classic looks with brighter colors: a seersucker jacket with brighter pants, for instance, anchored by a solid colored shirt. As a general rule to keep things classic but in style for the day, I ask ‘Would I wear this item any other day than during the Derby?’ If the answer is yes, choose a few brighter colors, and you have a great option to build up your wardrobe.”

So, while spring temperatures may be creeping up there, keep it cool both literally and figuratively, whether you’re celebrating at Churchill Downs itself, at a regional viewing party, or your buddy’s backyard.

And use the race’s quintessential mint julep cocktail as your inspiration: traditional, refreshing, and classic. 

Kentucky Derby Style for Men

Haspel Beignet Tan Seersucker Sport Coat
mens kentucky derby style outfits what to wear haspel beignet seersucker sportcoat 1

Joseph Haspel, Sr., took seersucker — a fabric with its origins in India’s British colonial period — and used it to create the iconic suit in New Orleans (where they know something about heat) in 1909. It’s practically the unofficial uniform of the Kentucky Derby, not to mention warm-weather dressing in general. While you can always go with the traditional blue stripe (or push your luck with green or purple), we like this neutral “Beignet Tan,” to function as the palette upon which the rest of your Derby Day outfit is assembled. If you really want to knock us out, go for the Magnolia White, but we do realize that’s a scary alternative where cocktails and mud may be involved. Haspel’s suit separates make it easier to find your perfect fit. Once you’ve got it, this combo will be your go-to for summer weddings and dress-up occasions. 

Phineas Cole at Paul Stuart Garment Washed Peak Lapel Sport Jacket
mens kentucky derby style outfits what to wear paul stuart garment washed peak lapel sport jacket

This unconstructed, cotton/linen blend jacket will occupy a place in your wardrobe for years to come, and, like your favorite pair of jeans, just get better with age. The peak lapel adds a bit of old Hollywood glamour, framing the face, adding height, and emphasizing the shoulders. This piece comes from Phineas Cole’s safari collection for summer 2019 is perfect for hot summer days when a jacket is still required. We like it with coordinating neutral trousers, so pair it with black or dark brown linen for added sophistication. 

Good Man Brand Soho Flat Front Stretch Wool & Linen Trousers
mens kentucky derby style outfits what to wear good man brand soho flat front stretch wool  linen trousers

We know what you’re thinking: “Wool?” Trust us on this one. Wool’s naturally built-in wicking properties are the perfect thing to help keep you cool, especially when blended with summer’s classic linen. The combo also makes for a crisp cut that maintains its shape with great texture. These indigo trousers are a perfect “non-neutral neutral,” brightening things up a touch for the season and functioning as a perfect base to build on with dress shirts, short-sleeved knits, and even a T-shirt for more casual events. We also wouldn’t be mad if you tried Good Man Brand’s charcoal option with either of the jackets above. 

John Varvatos Johnny Flat Front Shorts
mens kentucky derby style outfits what to wear john varvatos johnny flat front shorts

A head’s up…these (awesome) shorts may not pass muster if you’re headed to Churchill Downs itself for the big day. But if you’re headed to a viewing party at the local pub or a buddy’s house, check the dress code and the weather forecast. These shorts — with their minimal styling and linen/poly blend fabric — are a cooler, dressier alternative that look great on their own, but also pair nicely with a blazer. Again, we’re partial to the cornflower blue, but the rose and flint shades are great summer neutrals. 

Charles Tyrwhitt Non-Iron Tyrwhitt Cool Poplin Aqua Stripe Shirt
mens kentucky derby style outfits what to wear charles tyrwhitt slim fit non iron cool poplin aqua stripe shirt

The shirt is where we like to start building some serious color into our outfit. Like race day’s famous bourbon-blend cocktail, remember to keep things cool and tasty. In this case, in an appropriately minty, aqua shade. Charles Tyrwhitt’s “Natural Cool technology” is a 100% cotton fabric that’ll help keep things chill all day. 

Life After Denim Short Sleeve Oxford Shirt
mens kentucky derby style outfits what to wear life after denim short sleeve oxford shirt

I’m just gonna say it: Short-sleeved dress shirts smack of mid-century NASA scientists with pocket protectors (which could be, according to your own personal style, a good or bad thing). However, if you’re gonna do it, do it right, and choose a fitted style that’s clean and minimal. Life After Denim’s Oxford version adds subtle color and texture, with a silhouette that can’t be beat. The key is the perfect length of the sleeve — great for showing off those biceps and triceps you’ve been working on all winter. 

J. Press Emblematic Horse Racing Tie in Navy
mens kentucky derby style outfits what to wear j  press emblematic horse racing navy

That stringent “business casual” dress code no longer requires a necktie, but, hey…the Derby only happens once a year! Dress things up with a great tie, but let’s not get too carried away with novelty prints. This classic silk twill embroidered version is a perfect accompaniment to race day, but will also look elegant in your work or special occasion rotation. It will also raise your prep quotient to master level. 

The Tie Bar Red Wild Horses Bow Tie
mens kentucky derby style outfits what to wear the tie bar red wild horses bow

Nothing says Southern style like a bow tie, but please, learn how to tie one properly for yourself. The pre-tied versions get a lot of play, but honestly they’re a bit too “kindergarten” for our tastes. Again, grab a classic that has some heft. We like this patterned silk version, apropos to the occasion while paying a subtle homage to The Rolling Stones. 

Scotch & Soda Patterned Hat
mens kentucky derby style outfits what to wear scotch and soda patterned hat

Save that first sunburn of the season for Memorial Day Weekend (actually…just wear sunscreen then, too). Grab a hat to protect your skin while racking up some serious sartorial points. This lightweight straw fedora will serve you all season long. The hat is perfect when paired with a suit or jacket, but also a handsome addition to your beach togs. 

Thursday Boot Co. Lincoln Loafer
mens kentucky derby style outfits what to wear thursday boot co  lincoln loafers

Slip into something that’s both casual and sophisticated and that complements the cultivated vibe you’re pulling together for the party that’s as much about spring fashion as it is horse racing. These blue suede loafers look great with khakis, jeans, or even shorts, and the Goodyear Welt construction means you’ll have them for race seasons to come. 

Bogs Sauvie Slip On Boot
mens kentucky derby style outfits what to wear bogs sauvie slip on waterproof boot

As an alternative, keep an eye on the weather for race day, too. Depending on what part of the track…or your friend’s backyard…you end up in, having a pair of boots like these may just save the day. And, after all, if you’re at Churchill Downs, horses will do what horses will do. Be prepared. 

For more Kentucky Derby style, check out all the best looks from last year.

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