Style Scenario: Kentucky Derby Party

What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. The Derby is coming up, and it’s as good a reason as any to get together with friends and knock back a mint julep or some bourbon over ice. The guys get dressed up, the gals wear dresses and big hats, and it can end up being a complete blast. Here’s how to look the part while still having a few bucks left over to go to the window with (even if the “window” is a hat placed on a chair in the living room of the host’s house).

The Suit: J. Crew Factory Slim Seersucker Blazer ($84) + Matching Pant ($39 w/ TOOGOOD) = $123. You’re getting an entire summer suit for under $125? That’s pretty flippin’ good. And while blue and white stripe seersucker is more traditional… it can also look costume-y. Not so here. A nice, deep blue, but you still have that cooling seersucker pucker. Appears to have minimal lining too.

The Pocket Square: TheTieBar “Bouquet Toss” in Stone – $10. Bold and fun, but the muted tones keep it outta clown territory.

The Shirt: Amazon Buttoned Down Brand Tailored Fit Solid Pinpoint – $35. Or, whatever your favorite and best fitting white dress shirt happens to be. Button down collar absolutely works here. It’s a southern event, and the south is more conservative. So, button down collar is just fine. Plus, it’ll keep your points in line as the bourbon flows on.

The Sunglasses: Banana Republic Ervine Sunglasses – $46.80 ($78). Often on sale but not always on sale. Currently, the former, and 40% off. A bit of retro but still contemporary.

The Belt: Braided Canvas Woven Elastic Stretch Belts – $10.99. Eleven bucks on Amazon and well reviewed. Plus, since the shoes are suede-ish, you don’t have to worry about matching your shoes and belt.

The Shoes: Goodfellow & Co Kayden Loafers – $34.99. Faux suede here, so, these could be not great. But faux-suede has come a LONG way in the last few years. Fingers crossed that they’re not terrible? And, I mean, for $35, the threshold of expectation has to be reasonably low, no? Nice shape to em’. Perfect color to wear with the suit on a warm spring day too.

The No-Shows: Smartwool No-Shows – $13.95. A favorite. Far superior to cotton or cotton blends when it comes to no-show socks.

The Watch: Orient Bambino 2nd Gen Version II – $115. All class, and the retro good looks fit in perfectly with the fact that you’ll be watching a horse race.

The Reminder: Bring cash! Singles preferably. Here’s how to set up an easy functioning, self-serve betting “window” at a derby party. Take a piece of poster board or a white board, and make a row for each horse. Here’s an example using the 1973 Derby. Guests write their own name in the horse’s row they pick to win. They can pick multiple horses, and write their name multiple times if they want to increase their stake in the horse(s). Every time they write their name they pay a dollar into the pot. Each “name” in the winning horse’s row gets a share of the entire pot. Dress your board up with odds/jockeys etc.

The 2019 Kentucky Derby is Saturday, May 4th.