What To Wear To The Kentucky Derby

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The Kentucky Derby is, in many ways, a vestige of a lost time. When else in this day and age do people put on their Sunday best to watch a horse race? Or really, watch a horse race at all?

But getting dressed up for the Kentucky Derby is a tradition as strong as the race itself. And it's one that many people take very seriously, to varying degrees of success. Big hats, seersucker suits and lapel flowers the size of small dogs are oftentimes the order of the day. But, that doesn't mean you have to look like an extra from The Music Man to fit in or to have a little fun.

In an effort to llustrate how you can adhere to a theme and still look well-dressed, we combed through the Getty Images archives all the way back to 2005 to find style inspiration from Kentucky Derbies past that can help serve as a wardrobe guide for the big day. We scrolled past genuine celebrities, B-list celebrities, reality stars and people who appeared to have scammed their way onto the red carpet. Suffice it to say, when it came to well-dressed men at the Kentucky Derby in the last ten years, the pickings were slim. We did manage to find a few, but we can't tell you how many are better left behind us.

But, here's what we can tell you: take this advice with a grain of salt and have fun with it. The Kentucky Derby, or a viewing party at which people dress up, is one of the few times you can enter a room wearing something a little bit outside of the norm - or outside of your comfort zone - and know that you won't be the craziest looking person there.

So, whether you're heading to Louisville or watching from the comfort of your own home, here are a few guys who can lead you by their example. Emphasis on "few."


1. Ian Somerhalder


You never really need to button the bottom button of your suit, his tie could be tightened a bit, and I will never, ever be able to fully endorse a fedora. But, since this is the Kentucky Derby we're talking about, I can agree to look the other way temporarily. The point is that Ian Somerhalder wore a suit that fits him, and was able to introduce a little color into his outfit, too. I'm not sure where else he is planning to wear a suit with a visible turquoise tint, but it seems fine for a horse race.


2. Josh Henderson


Kudos to actor Josh Henderson for incorporating some of the traditional plaids that are always found on Derby Day into his look, while resisting the temptation to wear a head-to-toe suit in the fabric. An additional plus: he'll be super comfortable all day long, as evidenced by his mad chill thumbs up stance.


3. Hosea Chanchez


Actor Hosea Chanchez (don't worry - I had to Google him also) took a more casual approach to Derby dressing, pairing a cardigan with textured trousers. The pants dress it up a little bit, and the color blocking in his sweater give his look that little bit of lively pop. I would recommend forgoing the deep v-neck t-shirt in favor of a classic white crewneck, but overall, it's not a bad try.


4. Armie Hammer


Armie Hammer has the kind of WASP-y demeanor that is perfectly suited to both an event like the Kentucky Derby and to wearing a cream-colored suit. So really, it's the perfect storm of dressing for your type. Props to Hammer for not matching his pocket square, or worse, his tie, to his companion's hot pink dress. Overall, it's a mature look that is appropriate for the occasion.


5. Guy Fieri


Just kidding, guys!
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