It doesn’t take a genius to understand why guys would want to find the best shoes to wear with shorts.
There’s arguably no piece of men’s clothing that’s more breathable, laid back or easy to wear than a good pair of shorts.
But while they certainly feel great, it can be surprisingly difficult to pair shorts with the right shoes.
I like to say that shoes are the secret weapon of style, but when you’re wearing shorts that secret – much like your bare legs – is very much out:
Since there’s nothing but leg hair between your knees and your feet, your shoes are a lot more noticeable, which increases their impact on your overall look.
Plus, the best way to make a pair of shorts look sharp is to go sockless or wear no show socks, both of which limit the type of shoe you can get away with.
But while pairing your favorite shorts with the right pair of shoes can be tricky, it’s far from impossible.
In this post I’ll break down the types of shoes that look the sharpest, and share a few of the most affordable, stylish and all around best shoes to wear with shorts.
look sharp when you’re rocking shorts:
These are the Best Men’s Shoes to Wear with Shorts
Table Of Contents
- White Sneakers
- Boat Shoes
- Driving Shoes
- Penny Loafers
- Dress Shoes
- Canvas Sneakers
- Espadrilles
- Sandals
- Flip Flops (aka Slides)
White Sneakers
Work Best With:
- Khaki Shorts
- Denim Shorts
- Athletic Shorts
- Jersey Shorts
- Cargo Shorts
Why They’re Great:
Arguably the most versatile shoes of the summer season, a good pair of white sneakers is a warm-weather staple that can work with just about any type of shorts, and be worn on most casual occasions.
Sneaks have traditionally been considered some of the most casual men’s footwear, but it’s not hard to dress them up if you opt for a pair of minimalist trainers.
A clean, white pair of minimalist sneakers like the ones below can easily be paired with a good pair of chino shorts and a well tailored shirt to form a fashionable look that’s casual, but also sharp and well put together.
A Few to Try:
Boat Shoes
Work Best With:
- Chino Shorts
- Swim Shorts
- Linen Shorts
Why They’re Great:
Arguably one of the most iconic styles of casual shoes, boat shoes are among the best options any time you’re going to be around water.
Boat shoes always remind me of the classic casual look rocked by John F. Kennedy when he summered in Nantucket:
They convey a sort of timeless, cool and effortlessly stylish look, much like the casual shorts they tend to pair best with.
A Few to Try:
Driving Shoes
Work Best With:
- Chino Shorts
- Linen Shorts
Why They’re Great:
I like to think of driving shoes as kind of like the land-locked version of boat shoes.
They’re the perfect shoe to wear with casual outfits in the city because they give you a classic and smart look that’s a bit dressier than wearing sneakers, but they don’t have the same nautical vibes that boat shoes obviously have.
(Nor are they associated with a stereotypically preppy look, which is the one knock against boat shoes.)
Pretty much all the different shoe styles on this list fall under the heading of comfortable shoes.
But drivers are a particularly great option for all day wear because the rubber sole, which was originally intended to provide a good grip on car pedals, also makes them quite comfortable.
A Few to Try:
Penny Loafers
Work Best With:
- Chino Shorts
- Polo Shirts
- Button Down Shirts
Why They’re Great:
Penny loafers are the best choice if you want to achieve a “summer sophisticated” vibe, but don’t want to go all the way to dress shoes.
They’re dressy enough to wear to semi formal events like garden parties – which require dressing up a bit, but still allow you to wear shorts – but still give off a more relaxed look than a proper dress shoe.
But for my money, the main advantage of penny loafers is that they help you execute what I like to call The 10% Rule:
If you want to look sharp and stand out from the crowd, aim to dress 10% better than the average guy in any given situation.
So if you’re going to a party where you expect most guys to wear super casual styles, like sneakers, tee shirts and Bermuda shorts, you’ll look a lot more put together if you show up wearing a well fitted polo shirt, smart shorts and penny loafers.
A Few to Try:
Dress Shoes
Work Best With:
- Chino Shorts
- Button Down Shirts
- Polo Shirts
Why They’re Great:
A good pair of leather dress shoes allows you to push the style envelope even further than penny loafers, and achieve a more sophisticated and even elegant look.
There are two keys to pairing dress shoes with shorts.
First, since dress shoes are among the most refined styles of shoes, you want to make sure that you choose the right shorts and shirt to complement them.
In this case, the right style of shorts will have a slimmer fit and come in neutral colors, while the shirt should be either a slim-fitting dress shirt or a crisp, stylish polo that’s well fitted to your body type.
Second, opt for flat shoes that have sleek leather uppers, like the models listed below.
You can get away with a cap toe, but a full brogue or even a quarter brogue is a little too rugged for this look, as are the sort of chunky-soled shoes you’d wear in fall and winter.
Oh, and one more thing:
If you’re wearing black shorts, make sure you pair them with black shoes, never brown.
Combining black and brown is one of the most controversial looks in menswear – some say you should never do it, others say it’s totally doable. (Personally I’m on the fence.)
But even those who like the look would have to concede that it gives off a darker and more rugged vibe, which is more appropriate for fall than for warm weather.
A Few to Try:
Canvas Sneakers
Work Best With:
- Khaki Shorts
- Denim Shorts
- Athletic Shorts
- Jersey Shorts
- Cargo Shorts
- Long Shorts
Why They’re Great:
Canvas trainers get their own place on this list because they give off a distinctly different vibe than the minimalist white sneakers recommended above.
They’re an inherently more casual shoe choice, so you can’t really dress them up the way you can with crisp white sneaks.
But if the right footwear for you puts comfort first and men’s fashion second, then a smart pair of canvas sneakers can be your best friend.
While they’re obviously more casual than the different styles of shoes listed above, they’re still a much more stylish and elevated shoe choice than actual running shoes.
A Few to Try:
Espadrilles
Work Best With:
- Chino Shorts
- Swim Shorts
- Linen Shorts
Why They’re Great:
No kind of shoes are more laid back and relaxed than a pair of espadrilles.
As their international-sounding name implies, these slip ons hail from the Basque region of Spain, a place where afternoon siestas last for hours, pretty much everyone takes the entire month of August off, and casual footwear abounds.
Espadrilles make for a slightly more stylish and intercontinental alternative to the type of sandals that are easy to slide your bare feet into.
A Few to Try:
Sandals
Work Best With:
- Swim Shorts
- Linen Shorts
Why They’re Great:
Of all the different styles of shoes on this list, none are as casual as sandals – and none are as difficult to get right.
Making sandals look sharp is notoriously tricky, partly because there are so many damn options to choose from.
The various styles of men’s sandals on the market range from the refined, sophisticated and European-looking strappy sandals made of high-quality leather, to the thick, rubber kind that could best be described as “sports luxe.”
Unfortunately, many guys find themselves drawn to the latter, which are comfortable, but not much to look at.
In my opinion, the best thing to do is split the difference, and look for a pair of leather sandals with a comfortably padded foot base.
Additionally, there are two other crucial rules of thumb for sandal-buying:
First, never, under any circ*mstances, buy sandals with velcro on them. If you’re old enough to read this sentence, you’re too damn old for velcro.
Second, if your sandals have covered toes, they’re not sandals: they’re sh*tty shoes.
Either commit to the toe-exposing freedom of sandals, or pick up a pair of the espadrilles listed above.
A Few to Try:
Flip Flops (aka Slides)
Work Best With:
- Swim Shorts
Why They’re Great:
Last but not least, flip flops are the most relaxed type of shoe you can wear with shorts, because they’re barely shoes at all.
Sandals are already the most casual type of shoe you can wear, and flip flops are the most casual subset of sandals, which means there are really only a small handful of situations in which they’re appropriate.
On a hot summer night, you can get away with wearing a nice pair of leather sandals to a casual dinner on a patio.
But flip flops are really only appropriate when you’re lounging by the pool or on the beach, and want something you can easily slide your feet in and out of in between dips in the water.
Since they’re really more of a practical shoe, going with rubber versions is a safe bet, especially since they hold up well to water.
But remember The 10% Rule:
If all the other guys are wearing thick Adidas flip flops or those Quicksilver thong slides, then the guy who’s wearing a nice leather pair will look a lot more put together.
A Few to Try:
More Resources ↓
More Advice on Men’s Shoes fromIrreverent Gent:
- Release the Ankles! – The Very Best Shoes to Wear Without Socks
- The Best Men’s Summer Shoes
- These are the Most Stylish Types of Men’s Shoes
- The (Absolute) Best Casual Shoes for Men
- The Best Italian Shoe Brands for Men
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