Mens Guide: Dressing For a First Date


Dressing for a date, especially a first date, always requires some planning. What you wear depends upon the type of date, the time of day or night the date is taking place, and the location. The ideal outfit for a mid-afternoon coffee date is going to be drastically different from what one might choose for a romantic night out.

That said, today I’m going to be focusing on the dinner date. Most men just about have this one down to a science. If it’s a first, semi-casual dinner date they’ll press their favorite button down, usually one that matches their eyes, and pull on a pair of their nicest jeans or slacks.

Fine so far. Well done. You look good. You look so good, in fact, that you want to sabotage yourself, so you decide to throw on a pair of these:

Seriously guys, what are these? The description on the website called them “athletic-inspired.” I like to call them, “I don’t even like girls.”

It’s as though you want to say, “I like you, but I really want to keep this casual. I know enough not to wear my actual trainers, but, hey–look at these! As casual as a sneaker, but a little sleeker, and the suede accents really reflect my appreciation for the finer things in life; like yo ass.”

They are listed under the best-seller section on the website, which means there are quite a few of you out there strapping these things on, and that makes for a weird time for everyone. I’m here to break the cycle: throw them away, boys.

TAKE NOTE: Appropriate first semi-casual dinner date footwear:

Loafers–with dress socks. Black or dark brown. If you like a little flair grab a pair with a tassel or two. Not a whole lot of wiggle room when it comes to design, but the classic style also ensures that there’s not a whole lot of room to go wrong, either.

Oxfords. The good thing about this option is that you can get them in a variety of different colors with different levels of distressed leather, so you can opt for a really dressy pair, or a muted, more casual pair.

And seriously, that’s it. You have two options. Within those two options you have myriad shoes from which to choose, so get to it! She may not flat out thank you for your choice in footwear, but I guarantee she notices.

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