Custom Made To Measure Suits & Menswear | Boston & Newton

Sid Says


A Day at the Races

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Most of the time, sporting event ‘dress codes’ involve team colors and face paint. Don’t get us wrong, we love a good tailgate as much as the next fan. It’s just that the Kentucky Derby is a special weekend for us because it combines spectator sports and sartorial flexing.

Whether you’re down in KY or watching on the big screen, Derby & Oaks festivities are a great chance to flaunt your favorite springtime looks.

Racetrack Runway

Guys, even though you won’t be wearing the extravagant headwear favored by lady attendees, this is no time to slack in the hat department. A simple straw or Panama hat will shield you from the sun, and a colored band that coordinates with the rest of your outfit will have you looking like a real gent.

A seersucker suit is a smart, traditional option that will keep you cool. Pair with a patterned bowtie to complete the classic Southern look. If you’re ‘mixing and matching,’ pair the airy jacket with a bright pair of trousers.

If you’re aiming for a more modern presentation, consider a bold Italian sports jacket or shirt. There’s plenty of room at the Derby for bold plaids, prints and pastels, so throw a statement piece into the mix or have at it with fun accessories.

Playing Host

Our most important advice for your Derby party? Assess the guest list and stock mint julep supplies accordingly. Okay, there are plenty of other priorities for hosting, but this classic cocktail is a must. Use fresh mint and true Kentucky bourbon, lest you jinx your horse’s chances. New-school mixologists might toss in some rosemary or ginger for extra flavor.

Let your guests get creative with a sandwich bar featuring warm biscuits and salty country ham. An array of spreads, from Dijon mustard to raspberry jam, will give plenty of flavor options for this brunchy treat.

For sweet-toothed partygoers or a treat for the winners, serve up one of our favorite bon-bons, the bourbon ball. Try to score some of the originals from Rebecca Ruth, all rich chocolate and crunchy pecan.

The most important part? Picking a horse, of course. Whether your choice is based on sire or silk colors, this is a chance to cheer on an American pastime and celebrate in style. If your pick wins, then you just might have found a lucky outfit.