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9 Style Tips For Men To Do Derby Dapper

03|15|2018 < All Articles

The 144th Kentucky Derby will take place on the first Saturday in May and will draw visitors from around the world. And while the official dress code of the event is “smart casual”, attendees will be dressed across the entire spectrum of taste (and the lack of it), from “to the nines” to “to the clearance rack at Walmart”. Derby day, and the 2 weeks of revelrous events leading up to it, is a chance to dandy up, and for many men an opportunity to dress more daring than they otherwise might have the guts to. Here’s your homegrown but worldly wise guide on how to dress to impress and maximize all that Derby week has to offer.

1: Linen For The Win

As I mentioned, the weather could be all over the board. Opt for a crisp linen dress shirt in white, yellow, pink or lavender. Remember, the shirt should be the foundation for the rest of the attire, and rocking a pastel will set off items with bolder colors and patterns, and keep you cool all day. As always, make sure it fits properly, not baggy in the waist, too tight or loose around the neck, and that the cuffs end exactly at the bones of the wrist so that 1/2-1” shows under the sleeve of your jacket.

2: Suit Up or Mix & Match

Your jacket and pants combination is often the star of your ensemble, and there are two recommended routes: a classic suit or a blazer with contrasting pants. If opting for a suit, pastels are a great choice: dusty pink, rose gold, baby blue or even white in a linen or cotton blend can be a great choice and will offer many opportunities to wear throughout the summer. Seersucker is for suckers and will only make you look like a disheveled southern lawyer. Classic charcoal and navy suits are great, but too conservative for the biggest day at the track.

The other option is to roll with an interesting color combo of blazer and pants. A lavender blazer with white pants and purple shirt will turn heads. If you are more conservative, a classic navy blazer with pastel pink pants and white shirt is a great look, especially when set off with a bold pocket square.

3: Horse Shoes

Every trainer knows how important shoes are to their thoroughbreds performance at the Derby, and so should you. Leather or suede are your best bets. The aptly named Derby shoe, the classic loafer, the elegant Oxford or the timeless Monk Strap are all great options. Wing tips or other brogue patterns, especially with contrasting colors are recommended for the ultimate day at the races and will complete any thoughtful ensemble. Leave the tennis shoes for the tennis court and opt for classic staples at the track.

4: Knock Your Socks Off

No southern gentlemen would be caught dead at the Derby wearing socks. Current trends favor pants with a shorter break and no cuff, allowing ample opportunity for exposing bare ankles and great shoes. No-show socks will keep your feet comfy and afford the high water/no sock look. If you must sock up, select something festive and bright and leave the dark socks to the board room.

5: Derby is In The Details

Accessories can make or break any ensemble, especially on Derby, so picking the right combination of which to wear and the color and pattern of each allows virtually unlimited options to add a dash of color and panache to your look. The bowtie is the official neckwear of the Kentucky Derby and is a very popular, though neckwear that is worn under the shirt and directly on the skin, such as small scarves, bandanas, and ascots, is a great way to dandy up and separate yourself from the field. Pocket squares should contrast with your neckwear and not match exactly (so avoid those tie/pocket square sets), and they’re a great way to add style even if you opt to go tieless. Finally, a great pair of cufflinks provides a bit of bling. Opt for a vintage pair as a nod to the illustrious history of the event.

6: Put a Lid On It

Derby allows a man to pay attention to the details from mane to hoof, and that starts with a great hat. If you hadn’t noticed, hats are back in a big way. The weather on Derby Day is as unpredictable as the pony that will take home the Garland of Roses; early may in Kentucky could bring cold and rain or heat and sun, maybe all on the same day. A thoughtfully selected hat will offer style, protection from the elements, and absorb sweat. Straw or felt are great options, especially for classic hats like the Boater, Fedora, Pork Pie, or Trilby. There are many types of hats to choose from that would fit the occasion, but make sure it works with the rest of your attire and it will be the icing on the proverbial cake.

7: Smoke Your Barrel

Nothing goes better with the Kentucky Derby than a glass of Kentucky Bourbon. And nothing goes better with Kentucky Bourbon than a premium cigar. Much of Derby takes place out of doors, and certain sections of Churchill Downs allow smoking inside, so cigars are ubiquitous. Just do yourself and everyone else a favor: select a premium one that smells great and leave the nauseating cheap stogies and cherry blunts on the shelf. Pro tip: Carry several so that, like a proper Southern Gentleman, you cab oblige your friend that forgot his. Don’t smoke cigars? Derby is a great time to start.

8: Look Shady

Rain or shine, the Kentucky Derby will happen. Rain or shine, you’ll look like you know what’s happening in a dashing pair of sunglasses. Despite what Dusty Gibbons says, do not go get yourself a pair of cheap sunglasses, rather select a designer brand with a Polarized lens and metal frames. Aviators are always a great choice, or there are great new trends in round lenses. If all else fails, shades are a great way to hide your bloodshot eyes from partying too hard at the Oaks as well as hiding the tears you’ll shed over your loses from your ill-advised bets.

9: The Rack is Wack

Sadly, I must include this tip on the list. The vast majority of men, even those with the best intentions, are walking around looking as if they’re wearing someone else’s clothing. While tragic in the office and at the bar, it’s downright detestable at Derby. While you may occasionally find an article of mass produced clothing that actually fits, most often it’s not perfect. While more expensive, getting your Derby attire custom made for you will pay dividends. You’ll look and feel your best, and your clothing will be a reflection of your style and personality. You’ll understand that those who go custom refuse to go back to the rack.

For a Kentucky Derby to remember, call Harry at Ace Custom Tailors and schedule a fitting consultation. He’ll assess your wants and needs and can outfit you custom suits, pants, shirts and jackets. Ace also carries all the accessories that you need to Do Derby Dapper.

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