As much as I love boots, denim, and heavy sweaters, I still emerge from every Chicago winter longing for spring.
During the winter, I have to spend five minutes tying boots and getting dressed in battle gear just to walk to the corner store.
So the ease of being able to slip on my summer shoes and walk out the door becomes a greatly missed luxury.
How to wear summer shoes
Dressing for the season and weather is one of the hallmarks of well dressed men.
While you don’t have to strive for the full on country club look, it doesn’t hurt to have some lighter weight trousers, colorful patterned shirts, and a few pairs of summer shoes reserved specifically for the season.
More often than not, I wear all of my summer shoes sockless (read this article to beat foot odor while doing so).
And in modern times at least, going sockless is perfectly acceptable even in a formal city like Chicago. The summer heat just demands a more relaxed dress code.
For shoes, this typically means lighter colors, woven fabrics, suede, and slimmer profiles.
The shoes on this list are what I consider the essential summer shoes for men, roughly ordered from most to least formal.
1. Dress shoes
While not specifically a “summer shoe,” some dress shoes that lean a little more to the casual end of the formality spectrum can pair well with dedicated summer clothes.
They work best if you have more colorful socks or skip them all together.
I would avoid shoes that are made of black leather or those that are highly polished, as they’re just too hard to dress down.
Bluchers are much easier than balmorals (I explain the difference in my free eBook) to pull off in a casual manner.
- Lighter colors are going to be easier to wear casually
- Suede is a good option for warmer weather
- Look for earth tones and contrasting rubber soles
- Pointy or chiseled toes are more formal – instead look for something with a more rounded profile
- Choose bluchers over oxfords
- Broguing adds a casual element (also explained in my free ebook)
Recommended dress shoes
The second most formal summer shoe option is the leather loafer.
Their slip on construction makes them the perfect addition to a dressy look while still having the ease, comfort, and coolness you need for the hot days ahead.
You can wear these with a short sleeve button up and chambray pants, with a summer suit, or even with shorts.
- You may have to size down half a size to prevent slippage
- Unlined loafers will be cooler due to one less layer of leather
- Look for softer construction for a more casual look
- Rubber soles enhance comfort and traction in the rain
These summer shoes just make me think of an Italian Riviera vacation in the 1960s.
Sean Connery actually wore a pair similar to the ones above in his role as James Bond in Thunderball.
Sounds like a solid endorsement to me!
Espadrilles are perfect for transitioning from beach to boardwalk or just slipping on to run errands.
They look great with cuffed jeans, shorts, or even as part of a destination summer wedding outfit.
- Breathable mesh will help keep your feet cool
- Higher end espadrilles will have a coiled rope insole (very interesting detail)
- Rubber soles will help tremendously by the pool
- If you’re wearing them casually, try some bold colors
- Although they may not fit the technical definition, leather espadrilles are awesome
4. Boat shoes
I’ve already written a full review here on these jack-of-all-trades summer shoes.
Guys frequently view them as more dressy than they actually are due to the popularity with the wealthy East Coast crowd.
But don’t make the mistake of thinking these should be worn with a suit.
In my experience, they look best in casual summer settings and always improve with a little patina.
- Functional, 360-degree laces
- Siped soles
- Leather insoles to help prevent foot odor
- Since these are casual shoes, go for whatever color speaks to you (and there are plenty of options)
Recommended boat shoes
5. Classic sneakers
Sneakers are a great combination of classic good looks and functionality.
They aren’t nearly as fancy as dress shoes or loafers, but they provide a lot more cushion and probably won’t give you blisters if your day involves more walking than intended.
In general, unless you’re a master of your own personal style, I don’t think you should attempt to wear these with a suit or even a sport coat.
That look works perfectly for J.Crew models, but most guys should wear these in a strictly casual arena.
- If they look like they could’ve been worn in The Sandlot, you’re golden
- Look for canvas over leather to cut down on foot sweat, you’ll also be able to wash them if need be
- Some newer models are made of mesh making them the perfect summer shoe
- No need to go designer, the classic models are perfect
While you definitely don’t need to buy a pair of summer shoes from every category, having two or three wouldn’t hurt.
It’s also a good idea to give your summer shoes a day or two to breathe between wears.
A good starting rotation would be:
- Classic sneakers
- Boat shoes
This’ll ensure that you have options to change things up based on where the day will potentially take you and get you through events that vary in their level of formality.
All the best,