3 Ways to "Dress Up" Casual Vintage Shorts

We love wearing them, you love wearing them. Let’s face it: we all love wearing casual vintage shorts. They’re light, they’re comfortable, and they’re stylish. The only problem? Sometimes, you have to go places with a dress code, and casual shorts can feel a bit underdressed. Fortunately, our vintage shorts are versatile enough to be dressed up when you need them to be. Just follow these three tips, and you’ll be able to spruce up your outfit and head somewhere fancy.

Get the Shoes Right


Dressing well in shorts isn’t always about what you have on top, important as that might be. You should be aware of just how much of your legs are showing—and how vital it is to get them right. Here’s what you need to know:

  • Sandals and socks are a no-no. It’s such a controversial combo that it even has its own Wikipedia page. Not only are the sandals too casual for dressing up, but exposing that much sock is going to throw off the entire balance of your outfit.
  • Dress up the shoes. Should you wear sandals without socks? Not if you’re dressing up. Wear a pair of Buckingham or “Buck” shoes without socks and you’ll be much more restaurant-appropriate than you would be with sandals.
  • Keep it simple. In art, it’s called “negative space.” Sometimes, less is more. Tasteful shorts and shoes without socks in summer is dressy enough for the vast majority of venues.

Of course, that isn’t to say that the shirt won’t matter…

Wear a Shirt with a Collar


Take a gander at our woven shirts. Notice anything they have in common? They all have buttons and collars, making them button-downs that are perfectly casual, but still dressy enough to show that you did more than pick a T-shirt out of the closet.

A good rule of thumb for dressing up shorts is to wear a shirt with a collar, even if it’s a simple polo shirt. Generally, you’ll want a button-down (the more formal “button up” has no buttons on the collar) to avoid looking overdressed on top as you wear more casual shorts. As always, make sure the fit is appropriate—not too large, not too tight. You can even tuck in the shirt to “dress up” the outfit a little more.

Accessorize Properly

If you tuck in your shirt for a dressy look, you might want to consider a belt. Even though belts are more common with trousers than shorts, you’d be surprised at how this one accessory, when paired with the color of your shoes, can visually tie an outfit together.

Otherwise, keep the accessories to a minimum. A bracelet and a necklace look much more like beachwear than restaurant-wear. But a simple belt and watch could fit in just as well with a tailored suit, which means they’ll always give you that “dressy” touch you need.

Shop Vintage 1946 Today

Use these tips to put an outfit together with the right combinations of colors and styles. To build an outfit with confidence, shop our vintage clothing collections today to find the pieces that fit your style.