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 Unstructured Ludlow Seersucker Sportcoat & Pant – $266. Otherwise good seersucker suits are often ruined by heavy structure and gobs of cheap lining. That’s not the case here. A new addition to their unstructured & unlined suit separates line. Don’t want to invest in a full seersucker suit? Understood. A lightweight sportcoat and off-white chinos would work here too.

The Shirt: Charles Tyrwhitt Extra Slim Fit Non-Iron Twill White Shirt – $69.95. Or, whatever your favorite and best fitting white dress shirt happens to be. You should be able to nab this shirt for $33 as part of their ongoing three for $99 shirts site.

The Pocket Square: TheTieBar Dotted Hitch in Classic Blue – $10. Bigger dots here because smaller dots would clash with the smaller stripes of the seersucker (contrast is key when it comes to mixing patterns). Is a seersucker suit and polka dot pocket square a little… whimsical? Yeah. But it’s the Derby. Not a job interview (or a first date). So looking a little costumey is actually encouraged.

The Sunglasses: Tom Ford Retro Sunglasses – $159.97 ($380). Mega splurge territory, but, Tom Ford ain’t gonna be cheap even when heavily discounted. Sold via Nordstrom Rack. Wanna go cheap? Try these from UNIQLO.

The Reminder: Bring cash! Singles preferably. See #5 over here for how to set up an unmanned betting window at your party. And to avoid fisticuffs, keep it to a buck a name (not $5 or $10… degenerates will ruin the fun).

The Watch: Orient Bambino 2nd Gen Version II – $144.20. All class, and the retro good looks fit in perfectly with the fact that you’ll be watching a horse race.

The Shoes: Nordstrom 1901 Merick Derby in Cigar Suede – $110. A rich suede buck for not many bucks (sorry.) Ships and returns free via Nordstrom.

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 Belt: Banana Republic Suede D-Ring Belt in Brown – $44.99 ($59.50). No, your belt and shoes don’t have to match perfectly (or, at all) if they’re suede. Or hell, even if one of them is suede. Suede is a bit of a get-out-of-sartorial-jail-free card.

The 2017 Kentucky Derby is Saturday, May 6th.