Preakness Men’s Style

Horse racing has become synonymous with great men’s style. And that is especially true when it comes to some of the sport’s biggest events. Race-day style is about going all out, showing off some great details, and having some fun with your look. Over the years, certain piece have become bona fide race-day style staples—seersucker suits, bow ties, and straw hats, for example—and are absolutely classic options. Though I am a huge fan of tradition in menswear and men’s style, there is always a time to dispense with it and go a different way, which is what I did with my look for the Preakness this year.

Preakness Men's Style - He Spoke Style

Everyone does seersucker at the Derby and luckily there is no dress code for attending Triple Crown races. The combination of being a stubborn New Yorker by birth and having lived for over 10 years in a city that doesn’t like to be told what to do definitely contributed to my decision to disregard classic race-day style in favor of something different. A modern, slim fitting, custom blue three piece suit in place of seersucker for me. And no bow tie. I really wanted to rethink and reinterpret traditional race-day style at the this year’s Preakness.

Preakness Men's Style - He Spoke Style

It is possible to be bold without being outlandish and completely in your face. I’m not big on going over the top just for the sake of going over the top and prefer to temper boldness with a little subtlety. Though you could argue that there is nothing subtle about pattern mixing.

A race-day look just isn’t complete without a couple dandy details. You never have to twist my arm to get me to take out my pocket watch and a flower lapel pin is sort of like a cherry on top. Just like picking a pocket square to pair with a look, choose a flower lapel pin that fits in the color family of your look but that doesn’t match exactly. Every detail should work together and not in an overly obvious way.

Preakness Men's Style - He Spoke Style

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The spectator shoe is a true event shoe. You may not wear them often but they make a big style statement when you do. Allen Edmonds makes a great one called the Broadstreet, which is my personal favorite.

Preakness Men's Style - He Spoke Style

As I mentioned in my guide to men’s suiting options, if you are able to go the custom suiting route be sure to go all out with the custom details. Functioning sleeve buttons, a tab collar, and a two and half button jacket are not options you will typically find on an off the rack suit.

Preakness Men's Style - He Spoke Style

And definitely have a little fun with your jacket’s lining. It’s something that people generally won’t see, but when they do catch a glimpse of it, it is sure to turn a few heads.

Preakness Men's Style - He Spoke Style

Preakness Men's Style - He Spoke Style

Preakness Men's Style - He Spoke Style

This Look: Blue three piece suit by Quinntessential Gentleman Custom (similar here), Brown gingham shirt by Neiman Marcus (similar here), Striped tie by Brooks Brothers, Flower lapel pin by hook + Albert, Pocket round by Quinntessential Gentleman Handmade, Walnut calf dress belt c/o Allen Edmonds (Manistee), Walnut calf/bone spectator shoes c/o Allen Edmonds (Broadstreet), Pocket watch by Bellagio bel Tiempo (similar here), Silver t-bar pocket watch chain by Dueber Watch Company, Sunglasses by Ray-Ban (Clubmaster)

Thanks for reading.

Stylishly Yours,

He Spoke Style

Photography by Rob McIver Photo.


Chime In

  • Boswell

    Going through your just discovered blog and must say I like your style. But like so many style bloggers you have a tendency to go overboard. This outfit is what I’d call accessory overload. The left side of your chest has three items to draw the eye, then you have a pocket watch as well. Less is more.

    • Brian Sacawa

      Less is more. Definitely. And if you take a look around the blog a little more, you’ll see that that is generally the way I roll. This look was for the Preakness, where going a little overboard is de rigueur. Thanks for reading, Boswell.

  • Chaz

    I’ve been looking for a blue three piece suit for my wedding without much luck. Many of the blue suit options I’ve explored have been only available in a 2 piece option. Any advice on pairing a non-matching waistcoat with a blue suit?