What To Wear On a First Date

A first date is one of the only occasions when you definitely do not want to be overdressed

Here’s a question for you: in general, is it better to be overdressed or underdressed? We actually took the temperature on this a couple of years ago and everyone thought, overwhelmingly, that it is always better to be overdressed rather than underdressed.

The reasons for this ranged from the ease with which you could pare down the dressiness of an outfit more adding something to an outfit that would be considered underdressed to the very real concern of looking like a slob in a room full of well-dressed individuals.

While I too subscribe to the notion that wearing a tie to an event that nobody else chose to is better than being the only guy without one, there are certain times when being overdressed isn’t the best idea. And a first date is one of those occasions.

When it comes to dating, obviously looks aren’t everything. But it can never hurt to put your best foot forward. You want to demonstrate that you care about looking nice (hopefully on the daily and not just for the date) but without going overboard or seeming like you’re trying too hard to impress. A three-piece tweed suit might not be the best first date attire unless you run in some very fancy social circles.

A first date is also not a time to experiment. You want to wear what you’re comfortable in because people certainly act different when they’re wearing things that don’t feel like them. I think we’ve all been in that situation before. So what’s the best formula and how do you walk that fine line? Here are a few tips.

| WEARING | Billy Reid jacket, Lardini waistcoat, J.Crew shirt, Levi’s jeans, Cartier watch, Jack Erwin boots | PHOTOGRAPHY | by Rob McIver Photo

Keep it simple. Stick to the basics here. Keep the colors muted and classic – blue, brown, black. Seriously. A bright red shirt to you might seem like you’re putting some effort in, but it’s just going appear like you’re trying too hard.

Wear dark jeans. It’s likely your first date is going to be a mildly casual affair – drinks or small plates perhaps? – so forgo tailored trousers for a pair of dark blue or black denim.

Add style in subtly. True style is all about subtly and there are plenty of ways to achieve this. First, instead of an OCBD, why not try a chambray shirt? It’s got some texture, is a little rugged, and is a simple way to go above and beyond without going too far.

Next, add in something tailored like a waistcoat. Only try this if you’ve made a habit of incorporating a waistcoat into your regular style. If it’s not something you normally do, it’s going to be distracting for you and, by osmosis, for your date as well.

Boot it up. Women pay attention to a man’s shoes. Every guy wears shoes, but not every guy has a nice pair of chelsea boots. If you don’t already have a pair, get some and see if it gets noticed.

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style