Churchill Downs Duds: The Best Kentucky Derby Men’s Outfits of 2018

Page 1 of 10
1 of 10

One of the best things about The Kentucky Derby (aside from the day drinking and the possibility of winning some cash on a preposterous bet) is the fact that it comes on the first Saturday in May every year, rain or shine. This means, for the sartorially minded gentleman, there’s a whole year of deliberation to get your Derby look just right.

This year, it rained at Churchill Downs, and all those pre-planned pastels, pinstripes, seersucker, and linen suits were either covered in plastic ponchos or soaked through like this poor gent (though mad props to him for his bold use of a pink jacket, offset by a pastel green bow-tie and brought together by a classic black and tan fedora).

Despite the downpour, a few guys managed to pull off some pretty killer (and often low-key) looks. Here are the best men’s outfits from Kentucky Derby 2018, featuring an assortment of suiting styles and accessories. Let these guys be your guide for next year’s Derby duds.

Scott Serio/Getty Images
Michael Loccisano/Getty Images for Churchill Downs

Singer Shawn Stockman hits the Derby red carpet with a large-checked, blue and black plaid jacket; pastel-spotted shirt; and what appears to be a feather bowtie from our friends at Brackish. Stockman’s look is rounded out with classic black pants, polished shoes, and a pair of loud, contrasting socks.

Zach Bolinger/Icon Sportswire via Getty Images

Just look at this guy. From his sherbet-orange gingham suit, to his black and gold clubmaster sunglasses, to his all black chronograph, this dude’s got style in spades. No one would blame you for copying this exact outfit for Kentucky Derby 2019.


This guy’s light blue look is both dandy-ish and perfectly appropriate. With a gingham jacket, a cream-colored vest, a bright bow-tie that pops, and a newsboy hat to cap it all off, this gent has Derby fashion down to a science.

Robin Alam/Icon Sportswire via Getty Images

Bobby Hart may look like he just stepped offstage from performing in a barbershop quartet, but hell, why not? He nailed this combination of  light pink shirt, checked jacket with matching bow-tie, brown loafers offset by cream-colored pants, and a straw hat be-ribboned with colors that compliment both his patterned pocket square and his date’s outfit.

Scott Serio/Eclipse Sportswire/Getty Images

While this jacket may seem a little loud, it’s great for the Derby’s in-field style, which runs a little looser than what you normally find in the stands. We especially like the huge print — it really pops on an overcast day (which happens often at the Derby).

Dia Dipasupil (right) and Michael Hickey (left)/Getty Images

Modern Family star Ty Burrell hit the track with a classic blue blazer, gray pants, straw hat, and floral tie with matching sunglasses and boutonniere.


Seersucker and pinstripes are always an option at the Derby. Matching your date’s hat scores you points too.


Seersucker’s light weight and puckered nature makes for an extremely cool (in temperature and style) summer suit. Try this classic version paired with a pink, micro-gingham shirt, green bow-tie, and colorful pocket square. 


Finally, for those who want a little more heft in their outfits, a light tweed three-piece suit with contrasting buttons leaves an impression (and will keep you warm during a rogue Kentucky windstorm).

If you need some additional Kentucky Derby men’s outfit inspiration, check out this guide to seersucker and you’ll be prepped and ready come Derby Day ’19.

Page 1 of 10