When you throw on a pair of shorts, it always seems as though your shoe options are fairly limited. I think a lot of men either go with their go-to sneakers or a pair of flip-flops.
While I can always get behind a well-worn pair of sneakers, flip-flops I can’t abide. They’re lazy, and ugly, and I think only appropriate at the beach or in the shower. Which, ostensibly, leaves you with only the one option. I’m hear to tell you that there are other options out there, you just need to put a little more thought into how to build around them. In fact, I believe you can wear almost any piece of footwear with shorts if you dress appropriately to that shoe.
Summer means shorts and tees to most, so this will take getting out of your comfort zone a little bit. What I’m saying is, in certain situations it’s completely okay to wear dress shoes with shorts. What I’m also saying is you don’t merely get to sub in your dress shoes with for your worn-in sneakers and have that be acceptable. It’s not a terribly difficult concept to grasp, and I think we can figure things out with a few tips and tricks, like we usually do. So here’s what we think are the best shoes to wear with shorts, and why, because like in grade 9 math, we need to show our work.
Sneakers are pretty obvious. They work with everything you own, including shorts. When wearing sneakers with shorts I think they become even more versatile than they usually are.
Sneakers obviously work with shorts and a tee, but I think they can be worn with a dressier short and shirt as well. If you have a dinner out that requires something more than a ratty old tee, throw on a button-down oxford and tuck it in to a nicer short (read: not jorts or anything you cut at home) and wear it with your favourite sneakers. This fella here has it down to a science:
The fit of his shirt and shorts are on point, and works in a sneaker with that. The idea here is to play with the idea of dressy and casual. I think any variation on his look works too. If you want to add in more colour or pattern that works as well.
The key to wearing any sneaker in my mind is the proportions of your shorts. We all like shorts to be comfortable, but that doesn’t mean wearing baggy cargo shorts. Find something that sits above the knee and is relatively slim around the thigh. If you wear a baggy pair of shorts that sit below the knee it will throw off the balance of your look. If you have a tough time deciding on a good catch-all sneaker, go with classic canvas Vans or try something different, like these from Ami
This is an option I think many men do not, and would not ever consider. I get it though: the thought of it seems a bit ridiculous and tacky. I’m here to tell you, though, that when done right it’s quite a handsome look (as your mother would say. I actually say that all the time. Weird). Anyway, dress shoes are perfectly acceptable shoes to wear with shorts, but like I said, you need to be sure to pair it with the right shorts and the right shirt.
When I was speaking about wearing sneakers with an oxford or a dress shirt and shorts, this is a situation where you could sub in dress shoes. Or, in some cases, let’s say a garden party, wearing shorts, dress shoes, and a shirt/tie combo with a sport jacket is an excellent look. Here’s everyone’s favourite Nick Wooster showing us how it’s done
What it requires, like most things we talk about, is having the fit be spot on. A pair of shorts should fit like a pair of pants should: trim throughout. Pretty much any dress shoe will work too. Wooster chose to go with a heavy black monk strap, and the gentleman here chose to go with a caramel coloured lace-up. Slip-ons work quite well too, as they have a summery, casual air about them.
A classic option that will work with almost everything is a pair of Bucks, like these from Mark McNairy
They’re a great summer shoe and look good with a little bit of a patina to them. They can usually be found in a range of colours as well, so surely there is something there that will suit you.
To simplify, take a casual look you have in mind, one that requires a blazer and dress shoes, and substitute in a pair of shorts instead of the pants you would have chosen. It’s fairly simple and looks quite nice when the proportions and fit are done properly.
There are a few other options you may be thinking about, so we’ll cover those as well:
The point of today’s article is to equip you guys with the knowledge to try new looks. A dressy look with shorts shouldn’t be intimidating so long as you know what you’re doing. A lot of these looks are open to interpretation and can be easily put together from things you own or be found for not that much money.
Have the confidence to throw on shorts with a blazer and dress shoes, and embrace your inner Colonel Sanders. Any man who wears an all white suit and one of those weird black ties is someone we should all look up to. The chicken’s delicious too.