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10 dapper Derby Day fashion tips for guys

Try these 10 tips, guys, for stepping up to high fashion on Derby Day.
Sentimental Walk, by Francois Courboin, 1836, public domain

The Kentucky Derby runs annually on the first Saturday in May at Churchill Downs in Louisville, Kentucky. And fashion trends run high for the primo horse racing day – across the board.

From horsemen to handlers, celebrities to star spotters, and bettors to billionaires, racing fans deck out in dandy duds for the day. Some score big in the style department, while others fall flat.

Try these 10 tips, guys, for stepping up to high fashion on Derby Day.

These simple, but stylish, guidelines can keep you on-track and in the winner’s circle, when it comes to Derby Day fashion for men. Fashion sense for this perennial sports holiday applies at the track and at off-site celebrations.

Nope, Derby fans need not rent tuxedos. Still, certain fashion tips apply.

1. Discard the denims.

Blue jeans are capital for casual Fridays and everyday horsing around, but not on Derby Day. Real pants are de rigueur. Properly fitting chinos or trousers are suitable.

2. Ban the breeches.

Riding breeches (and jodhpurs) are off-limits on Derby Day, except perhaps for those who actually saddle up for the occasion. Jockeys, outriders, mounted reporters, and other riding personnel have their own apparel requirements.

3. Keep the jockeys where they belong.

While human jockeys work hard to stay on their horses, whether cameras spot them or not, the other kind should be tucked away out of sight.

4. Toss the tees.

Save the fascinators for the females’ foreheads. (Fascinators are freaky anyway, but that's another story.) Trendy and topical tee shirts may be suitable for everyday railbirds, but not for Derby Day. Pick a high-quality light and bright, crisp and clean polo or button-down shirt for the occasion.

5. Try a tie.

The most polished Derby Day dandies wear festive neckties, ascots, or bowties over classic shirts. This can be a fabulous way to show off one’s own taste and personality in a buttoned-up outfit.

6. Tuck it in.

Sure, some of horse racing’s elite may ride in on other others’ coattails (or shirttails). But men’s shirts are pretty universally tucked in for this dressed-up day.

7. Buckle up.

Leave the beer or rodeo buckles at home, and strap on an understated quality belt for Derby Day. Of course, that assumes the pants are tailored enough to have belt loops.

8. Jump into a jacket.

A classic blazer or suit jacket, usually constructed in cotton linen or seersucker, is practically a Derby Day requirement for most guys.

9. Sock it to ‘em.

Even if the weather cooperates, bare ankles are pretty much a Derby Day don’t. Socks are a plus.

10. Skip the sneakers.

Well-heeled Derby fans sport dress shoes. Understated quality is always a safe bet.

Don’t forget the crowning achievement.

And, of course, a stylish hat tops off a properly attired man’s look for Derby Day. A boater, derby, fedora, or panama is always a good choice. A top hat is ideal with the most formal outfit. Generally, baseball caps, berets, coonskins, and cowboy hats (unless you're Derby-winning trainer Chip Woolley, who can write his own rules) are not much seen on Derby Day.

Women’s fashions may be wild on Derby Day, while men’s are often more traditional.

Certainly, festive colors and fabrics are often seen on fashionably adventurous guys, from the primo viewing sections to the paddock fence.

As a general rule, tailoring is tops for men on Derby Day. Well-fitting ensembles come in every price range. Great cuts and flattering lines make all the difference.

Hey, you never know who you might run into on Derby Day – at the track or at a local gathering.

Of course, all bets are off for those who camp out on the infield at the track, especially on a rainy, muddy Derby Day.

Known also as the Run for the Roses, the Kentucky Derby represents the first jewel in Thoroughbred horse racing’s Triple Crown. To many, Derby Day also stands as an unofficial start of the summer season.

Here’s to fast horses and spiffy styles for Derby Day.

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