What I Wear on a First Date?

My style in three words is classic, comfortable, and simple. I lean toward a classic, masculine style, but I incorporate contemporary accents—like an oversized fit—for comfort and subtle visual interest.

I don’t have a big wardrobe, nor do I have any intention of having one. I like to have a small wardrobe of well worn, well loved pieces, that are suited for work, travel, or a night out in New York City.

Lately, I’m really starting to hone in on my personal uniform. Here’s the formula:

• Leather footwear
• Wide or straight-leg pants
• Oversized button-up

Dates are all about first impressions and what you wear is a big part of that. I like to say that your outfit is a biography. Dressing well for me is about respecting your date, but more than anything, respecting yourself.

For dates, I’ll wear my style uniform of a black leather footwear, wide or straight fit pants, and a button up. I’ll choose my more elevated pieces to make it special.

A freshly dry cleaned dark pleated trousers.

I’ll polish my black leather shoes.

I’ll steam my shirt so that it’s looking nice and crispy.

I finish it off with three sprays of my go-to weekend scent—one on each wrist, one on my neck.

And just like that, I’m ready to go.

First Date Fit