What to wear on a date without looking like you’re trying

By 06.26.13

If some guy on the Internet tried to tell me how to dress for a date I’d tell him to go to hell. And rightfully so. But that doesn’t mean I haven’t been in a situation where I’m going out with a girl I met the week before and wondered, “what the fuck am I going to wear?” So with that sentiment in mind, here are seven outfits to give you some ideas. And if you don’t have a date, feeling and looking good just might help you pick up a free-agent.

1. Jeans and a t-shirt


Triumph T-shirt, Rogue Territory denim, Nike for J.Crew sneakers

There’s nothing simpler than jeans and a t-shirt so when it’s appropriate take advantage. A day date in the park, a festival of any kind, or breakfast at a nearby cafe. Here’s a pair of kicks that are classic and a t-shirt with a motorcycle on it. What more is there to say. Oh, make sure they’re clean.

2. Shorts and a button-down oxford



Polo RL blue chino shorts, J.Crew shirt, Clarks dessert boots, Moscot sunglasses

Wearing shorts can be awkward for some guys. If many of us had the choice we would avoid leg exposure outside of the beach or pool. But sometimes the heat makes the decision easy for us. A faded short gives a beach vibe and throwing it on with a crisp white oxford adds a little sophistication. the dessert boots give you a little more substance than a boat shoe or sandal. Throw on some shades and you’re done.

3. The jean jacket



Levi’s denim jacket, Club Monaco henley, Red Wings boots,
Carhartt chinos, Moscot glasses

Ladies love jean jackets. Why? Nobody knows. I guess it’s just one of those mysteries that will continue to puzzle scientists. It might be all of the iconic figures from the 60’s and 70’s who made them famous (Brando, Martin Sheen, The Boss). So go ahead and get a piece of their mojo, just don’t wear the same color denim jeans with it. If you do you’re just wearing a Canadien tuxedo.

4. Navy and khaki



The combination of Khaki, navy, and white or light blue is a staple for the europeans. French guys lean on this look a lot and there is something to be said for it. It’s country elegance, what they would call provincial and it’s not at all related to what southern hill-billys call country. Take a page out of the euro playbook and you’ll look like a playwright, or at least someone who’s been to a museum, once.

5. Jeans and a blazer



H&M blazer, J.Crew shirt, Clarks dessert boots, A.P.C. jeans

If there’s something a bit classier on the docket you can’t go wrong with the blazer and jean combo. It’s training wheels for a suit and it strikes a balance between being dressed up and a “I still don’t give a fuck” casualness. If you wear this out to a more formal establishment you’ll be considered “dress appropriate” and look cooler than the banker d-bags wearing suits and ties(apologies to any bankers).

6. The grey sweater



New Balance sneakers, Gap sweatshirt, Levi’s 511’s

The grey pullover sweatshirt is just a classic. It looks good and nothing feels better. You can have the same one for years (granted you don’t get too many stains) and it will only get better with age. Perfect for a movie, she can nuzzle into it and you’ll stay warm in the freeze locker they call a theater.

7. The full suit



Suit Supply suit

In the movie Tropic Thunder, Robert Downey Jr. famously said that an actor should “never go full retard.” While that might be true for thespians, when a guy puts on a suit he should go “full suit.” Don’t be one of those wanna be suit wearers with the untucked shirt, no tie, and sneakers. Wtf is the point? Save the suit for when it’s appropriate and wear it the way it was meant to be worn. If you take a girl somewhere where she gets to dress up and you look like James Bond, your work is done.

TAGSDating adviceDating tipsfashion advice for menmens fashion adviceThe Library

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