Picking Out Shoes for Your Shorts

If you’re shopping at Vintage 1946, it’s safe to say that you have good taste in shorts. You pay attention to your style, and you like picking out the right shorts to suit your personality, and you know what’s in fashion.

The problem: one pair of shorts does not make an outfit.

You have to have articles of clothing that go with your shorts if you’re really going to make an impression, and the outfit starts from the bottom up. In other words, your outfit begins with your shoes. When you wear shorts, your shoes are emphasized more than ever: they’re little islands, down there, drawing the eye. The first thing to kill a good look is wearing the wrong shoes with your outfit. If you want to get noticed, then it is necessary to choose the right shoes to wear with your shorts.

Types of Shoes and When to Wear Them

It’s a harsh truth that there are shoes that go well with shorts, and shoes that don’t. In some cases, the combination of shoes and shorts might be situation-dependent. But let’s look at a few shoes-and-shorts combinations that definitely do not work:

  • Socks-and-sandals. Sandals? Yes. If you’re at the beach. But sandals with socks? No. They make you look like a tourist who’s dressing himself outside the office for the very first time. Yech. Not a great impression to make.
  • Dress shoes. Your oxfords might look great in a suit, but with shorts, the formality goes above and beyond what you can hope to achieve with shorts. Some people wear shorts with suits, true, but it takes a bold and sartorially-seasoned person to pull off that kind of unorthodox look.
  • Even the ubiquitous chukkas don’t quite go with shorts. Shorts call for a more casual shoe; certainly not a boot that’s meant for doing more heavy lifting than can be accomplished in an outfit of shorts.

Of course, there are all sorts of shoes that do go well with shorts in many situations, including:

  • Boat shoes
  • Suede Bucks
  • Loafers
  • Sneakers
  • Sandals

Choosing the Color of Your Shoes

Can you pick up just any pair of boat shoes and match them with your shorts? Most of the time, yes: that’s the advantage of boat shoes. But you’ll want to do some color pairing to make sure that your outfit looks well put-together and not hastily assembled:

  • When contrasting, don’t over-do it. Bright white sneakers and a pair of black shorts make you look like you’re going to the gym, not to a casual dinner party. However, a bold blue pair of boat shoes with a pale red pair of shorts? That’s more like it.
  • Matching can work, particularly if you have other items to offer come contrast. White shoes and white shorts are great for very hot days. The trick here is that you generally want to match a belt with your shoes, so you’ll often need to find some other way to make a matching outfit pop.

Picking shoes to correspond with your shorts isn’t rocket science; but it’s not something you should merely leave to chance and what you spot first in your closet. Give it some thought and you’ll be sure to be the most well dressed man in shorts no matter where you go.