The Best Men's Shoes to Wear with Shorts

A young man wearing shorts and canvas sneakers
Michael Heffernan / Getty Images

When the sun comes out, it’s often coupled with the first sighting of a man wearing shorts and dress shoes. We can’t have that. 

Deciding which men's shoes to wear with shorts is confusing to many, but it doesn’t have to be. While it’s not as easy as deciding what to wear with jeans, you can still look great whether you’re going to a company picnic, family reunion or to watch your kids play soccer.

 

One thing to keep in mind when deciding what to wear is actually where you physically live. Now, out West where I am, things are a little more casual and I can get away with wearing shorts almost anywhere, but back East things are a bit more formal. If you’re unsure about what’s appropriate, always err on the side looking a little nicer. It’s a good rule of thumb that will serve you well. 

Let’s break this down into three situations that you’ll likely find yourself in this summer. Follow these suggestions for choosing men's shoes, and you’ll look great in a pair of shorts.

With Casual Shorts

Think of “casual” as hanging around on the weekend, running errands or hitting the beach. You’re not looking to impress anyone, but you don’t want to look bad either. 

Reef Flip Flops for Men: Any flip-flops will work, but these are insanely popular, durable and never disappoint.

The Keen 'Kanyon': These are a great all-purpose combination of shoes and sandals.

You can be incredibly active and still look hip.

Converse 'Jack Purcell' Men's Canvas Sneakers: You can’t go wrong with Converse sneakers and the new “Jack Purcell” will look great with any pair of shorts.

On the Town

I define “on the town” as any situation where you need to look respectable, but not dressy.

Great examples are the annual 4th of July BBQ, a baseball game with the guys or drinks with your wife.

Sperry Top-Sider ‘Authentic Original’ Boat Shoe: It seems like guys have been wearing “Top-Siders” as long as they’ve been driving boats. These dress you up a bit from Keens or sneakers, are really versatile, and have a great sole for wet-dry traction. Great whether you’re by the pool or on the boat.

Polo Ralph Lauren Faxon Low Sneaker: This canvas sneaker is a great option for those looking for a minimalist shoe. It looks great with all types of shorts and is comfortable to wear in hot weather. 

Merrell Terracove Delta Sandal: Great, lightweight, stable leather sandals that show you care what you look like, but still allow you to be comfortable. You wouldn’t want to wear these to work, but they work great in most social situations.

For a Nice Occasion

There’s a really fine line here because shorts are very rarely (if ever) acceptable when you need to look your best. You don’t wear them to work, to church and you sure as heck don’t wear them to a wedding. This is for when you want to look good, but can still get away with wearing shorts. 

• Johnston & Murphy 'Golson' Sandals for Men:  The first thing you notice after the high-grade leather is that they have a capped toe.

When getting ready for any situation that isn’t casual, don’t show your feet. Live by this rule and you’re ahead of the curve. These are classy with just the right amount of luxury involved.

These are the only type of men's shoes that you would wear with shorts. If there’s a style of shoe you’re wondering about such as loafers, dress shoes or boots – the answer is “no.”  Shorts give a unique opportunity to look really good or grossly out of place. Choose the former, not the latter.