Derby & Steeplechase Fashion for Men: What to Wear & How to Wear It

//Derby & Steeplechase Fashion for Men: What to Wear & How to Wear It

Derby & Steeplechase Fashion for Men: What to Wear & How to Wear It

The 2017 Kentucky Derby is only days away and Steeplechase season is already here but some men are stumped on what to wear. Horse racing events allow men – most notably southern men – a chance to break out of our khaki and blazer fashion shell and add a bit of color to the mix. Here are some ideas for gents to consider and thanks to and Vineyard Vines for their words of wisdom too. At the bottom are places you can purchase some of my suggestions. 


Thinking about adding color to your derby-day? Pants are an easy start and bright, bold solids are an good way to stand out in the crowd. Vibrant colors like Key Lime, Ocean, Pink, and Citron are good choices. Combined with a navy blazer you can add additional colors with a bow or long tie and pocket square. But please, never, ever, purchase or wear a tie and pocket square that are identical patterns. 



Now that you have the pants you know that you’re going to have some fun with the shirts. A great dress shirt in a complimentary color will go a long way. If you’re wearing bright pants or seersucker, I would recommend going with a solid pattern so you can add more depth and color with a tie. However, if you are not wearing a tie, a larger and bolder pattern with solid bright pants is the way to go.

Blazers, Sportcoats and Seersucker

The jacket is what brings everything together and you can’t go wrong with the classic navy blazer. It’s the most conservative look and if you’re a tad uncomfortable in venturing too far from your banker wardrobe, then play it safe by adding color in your tie.

However, if you want to have a little fun on top though, madras or bright colored sport coat makes it easy to turn heads.

For me, seersucker is an easy choice and is perfect for those warm summer afternoons. And speaking of color, this is where you can really get bold with seersucker. Because I’m so comfortable wearing this material, I don’t mind going toward brighter colors, however, I always provide a word on seersucker; if you don’t feel comfortable and confident wearing it, don’t. It’s as much as “attitude” as a fabric.



Most gentlemen wear a necktie, but a bow tie is always a great option. If you never wear bows, try it out and you may like it. As the official style for the Kentucky Derby, Vineyard Vines offers an assortment of Derby-themed ties and bowties that will make every man look dapper and distinguished.


Vineyard Vine Ties (StyleBlueprint)


For heaven sakes, leave your black wingtips at home. That way they’ll look great for Monday’s loan committee meeting.

There are lots of bit loafers out there and everyone has their idea of who makes the best ones. The most important thing you need to know is that they should be worn without socks. If you’re wearing seersucker, white or dirty bucks are always classic. Brown and white loaders work too.


Top it all off with a fedora or bowler hat for the complete Kentucky Derby look. Men’s Derby hats are generally solid in color and inspired by the style from the 1920s.

Now you are ready to throw back some bourbon (Maker Mark or Bulleit are my go-to’s) and tie on a bowtie. The most important thing about your Derby outfit for men is to be “confident.”

No matter what you wear, it’s how you wear it gentlemen.

Wear to buy men’s Derby & Steeplechase fashion:

Vineyard Vines

Oak Hall, Memphis, TN (ask for or see Johnnie 901.761.3580)

Hinton & Hinton, Oxford, MS (ask for or see Garner Hickman, 662.236.1381)

Dixie Pickers, Collierville, TN

2017-05-03T09:46:33+00:00 May 3rd, 2017|Fashion|0 Comments

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