Want to learn something of value about a man? Don’t ask him what he does, who he loves, or where he comes from. Just take a gander at the shoes on his feet, and the cocktail in his hand.

In the first edition of our shoes and booze series, we’ll spend some time with a sleek pair of loafers and a classic cocktail from the Golden Age of Hollywood. Let’s start with the shoes.

The Caine Bit Loafer

The bit loafer is named for the eye-catching hardware across the tongue which resembles a horse bit. A veritable staple of twentieth century Ivy League frat fashion, the bit loafer was designed for a man of leisure with an eye for detail.                                                                                                                                                                          You might only catch a fleeting glimpse of the glint of the bit loafer’s striking fleur-de-lis adorned hardware as the wearer dashes across town to catch up with his old Skull & Bones buddies. Here is a man who tossed off his reigns but kept the bit as a memento of his humble origins.

The bit loafer might not have the universal appeal of the tassel or penny loafer, but the man in the bit loafer isn’t after your praise and admiration. As far as he’s concerned, you can keep your two cents planted firmly in the tongue of your penny loafers.

The Brown Derby

Back in the 1940’s and 50’s, The Brown Derby was a popular Los Angeles restaurant chain known as a gathering place for the Hollywood elite of the day. It’s also the alleged birthplace of the Cobb salad. Safe to say the clientele was a bigger draw than the menu. The restaurants are now defunct, but their legacy lives on in their killer cocktail namesake.

The Brown Derby is a bold bourbon drink with a big personality and a short ingredient list. Like the bit loafer, it’s a deceptively simple design accented by a fortifying dash of citric glitz.

To make this Hollywood inspired hooch, all you’ll need is grapefruit, honey, water, and Kentucky bred bourbon whiskey.

• Start with 2 oz of your preferred bourbon.
• Next, combine equal parts honey and water and add ½ oz of the mixture to your cocktail shaker.
• Top it off with 1 oz of fresh squeezed grapefruit juice.
• Add ice, shake, and strain into a coupe glass.
• Finally, garnish with a twist of grapefruit.

Here, we have a simple cocktail for a man on the move - a distinctly modern drink with a knowing nod to tradition. If there’s one thing that can keep your eyes off the sheen of his Italian leather loafers, it’s the warm golden hue of the whiskey drink he sips as he daydreams absentmindedly on his two hour lunch break.

Don’t get caught drinking an old fashioned in a pair of Hushpuppies. Stop in today, and see yourself in a pair of Paul Evans’ signature Italian bit loafers.