Warm weather and summer events make for special shoe demands, so you want to be prepared with the right summer footwear. You want shoes that are going to keep you cool and also look stylish with your summer looks. One caveat before we jump in though: while you may be tempted to wear flip flops all summer, don’t do it! Unless you’re headed to the pool or beach you should be wearing a proper shoe, so keep them in the closet unless there’s water present.
Don’t forget to check out all of our picks below!
Boat Shoes
A summer classic, these are great all around casual shoes. Stick with the classic style in leather and look for colors like brown, tan, navy, or grey. Despite what you may have seen, these aren’t meant to be dressed up though, only wear these with shorts and very casual chino outfits.
A stylish warm weather canvas shoe, espadrilles are very lightweight and breathable. These look great with everything from shorts to chinos and you can get them in solid colors or go for a fun pattern.
A great casual shoe with a little more polish, you can wear driving mocs with everything from shorts to chinos and a blazer. I recommend these in suede over leather because in the warmer months leather can just look a bit to heavy and formal. Two rules about drivers I always see guys break: never wear them with a suit (too casual), and always wear them without socks or with no-show socks.
When you’re talking about versatile, stylish footwear, there are few styles I like better than loafers. I love that they can be dressed up or dressed down, and work for pretty much every season. There are many varieties out there these days, from simple to complicated, but I’d like to focus on three primary types that deserve a place in your closet, plus a few that maybe don’t. Get ready, it’s loafer season for a reason.
Penny Loafers
A classic style that has stood the test of time, penny loafers are perhaps my favorite out of all the loafers. I love how versatile penny loafers are, they can be dressed up with a suit or dressed down with everything from jeans and a buttondown to chinos and a polo shirt. Brown and black are the two ideal colors here. For a secondary choice, a classic burgundy or oxblood color is an excellent option.
Originally designed for, you guessed it, driving, I love this style because they’re super comfortable and work well in a variety of casual situations. They come in a few variations but I prefer the versions with a nubbed rubber sole or a full rubber sole for the look and comfort. For colors, the basics like brown and tan are great of course, but I also recommend versions in grey or navy for a pop of color.
Another shoe that evolved from function – the no-slip rubber sole and lightweight design worked well on boats – boat shoes have become a classic warm-weather staple. I like them best with chinos and shorts for a relaxed alternative to sneakers. On the color front, go with blue, brown and grey for maximum wearability.
There are a few other loafer styles out there but I don’t generally recommend them because they can lean too specific in their look and style.
Tassel Loafers
This dandy look is popular with a lot of style bloggers out there, and while I don’t hate them, I just don’t think they’re ideal for most men from a style standpoint. Just like your clothes, your shoes should be streamlined, and while the tassels can give them somewhat of a “distinguished” look, I find them to be distracting, like an untucked pair of shoelaces.
Horsebit Loafers
Another type with a dandyish vibe that has become popular again (you may know them as Gucci’s iconic loafer), I am not a fan of them at all. They immediately age you up (and not in a good way), and I always expect a lawyer or Wall Street guy who is trying way, way too hard to wear these.
Venetian Loafers or Smoking Loafers
Both of these have a similar, streamlined shape and a formal look. Venetian loafers are unadorned and usually in leather while smoking loafers are typically velvet and have embroidery or embellishments on top of the shoe. I always view these as super formal, and that’s why I really only recommend wearing the patent leather or velvet versions with a tuxedo if you want to add some flair. I don’t recommend more casual versions in regular leather because it’s a style that’s quite outdated and doesn’t have the versatility I like.
In my Men’s Wardrobe Essentials Series, as well as my Summer Essentials Ebook, I touched on shoes a little bit, but the most-requested video/article for a while has been the number and type of shoes every man should own.
So here it is: These are the quintessential shoes that every man should have in his closet for year-round wear. Anything outside of these are specialty items, like snow boots, so they’re not included in this article.
There’s nothing better than a sleek pair of athletic shoes. Not only can they function as your gym shoes, but they can be worn with your casual outfits, as well.
I recommend sticking with a black/white, black/grey/white (like above), or navy/white color to ensure that your sneakers compliment all your outfits. Other crazy colors like neon green or a bright red will only draw attention away from your outfit which is why I’m not recommending those colors. You probably wouldn’t know it, but these shoes are one of my clients and almost a year old.
Since all of the shoes I’m recommending have white soles, I highly recommend Jason Markk’s Essential Shoe Cleaner Kit. Just give the soles a quick scrub with the included brush and soap every few weeks and they’ll look good-as-new for a long time.
The second pair of shoes you should own, is what I’d consider an absolute essential to any well-dressed man’s wardrobe, which is why they were also included in my Men’s Wardrobe Essentials series.
Under no circumstance should you wear these with a suit, though. That’s a trend that’s been floating around for a few years and I just think you’re not doing a suit justice by dumbing it down with sneakers.
A quick note, because it’s been brought up in the comments of my White Sneaker Video – Jordan’s and Air Force Ones are not the same as these – even if they’re white – because the shape and profile of those shoes are completely different. Notice how sleek and simple the profile of the above shoe is – THAT’S what makes all the difference. Jordan’s and Air Force Ones are chunky looking and have a very specific look that a lot of men can’t pull off.
The third pair of shoes you should own are suede driving moccasins. I’ve already covered these in my Summer Essentials Ebook, but they’re also great shoes during the other parts of the year, depending on your climate.
If you’ve never worn a pair, then you really should try them because they’re the most comfortable middle ground between a dress shoe and a sneaker and after they’ve been broken in a little bit, they’ll feel like you’re wearing a pair of socks.
I have these ones here by Tod’s that I really love. Stick with dark brown first, then you can add a tan color and then navy which will cover you for any outfit you can wear outside of a suit – which you should never wear driving mocs with. The construction is fantastic and they hug your feet nicely – which is important because a lot of cheaply made driving mocs tend to look loose around your feet which is to be avoided.
There’s three things to remember about driving moccasins:
Only wear no-show socks with them. I did a whole video about socks so check out the link in the video description. Before you wear them for the first time, make sure you Scotchguard them in order to protect the suede from dirt & liquids as much as possible. They’re going to get dirty, it’s inevitable with suede. So buy them knowing they’re going to have a shorter shelf life than the rest of your shoes, but trust me, you won’t care because they’re so damn comfortable.
The fourth pair of shoes you should own are Oxford or Derby dress shoe with a sleek profile and round toe. I’ve covered these extensively before, but every man needs at least a black and possibly brown pair of dress shoes in his wardrobe. They go well with all outfits outside of a super casual outfit (think: t-shirt and jeans). And since you should at least own one suit, these are necessary because you can’t get away with wearing any other shoes with your suit. Remember: the goal is to have you looking amazing, no matter the scenario or outfit.
I prefer plain toe, but you can also get cap toes, but I will grab a pair of plain toed Oxfords or Derbys over any other kind of dress shoe 99% of the time.
As for brogueing, burnished toes, oxblood or other unique colors, don’t get me wrong, I love them, but that’s like two levels down the road if you’re new to dressing better. They’re very specific and won’t go with a lot of your outfits, so grab them after you’ve invested in a classic black and dark brown oxford.
The final pair of shoes – in this case – boots you should own are a pair of brown leather boots. They’re utilitarian in that you can wear them in a lot of adverse weather situations as well as in more elevated casual outfits. I prefer brown because boots are usually more geared toward the cooler months, and brown is a great fall/winter color and it goes AMAZINGLY well with the dark wash jeans and wool trousers you should already own. But don’t be mistaken, you can also wear these year-round.
It’s been asked this a few times by viewers, so unless you’re going for the lumberjack or American/Japanese worker-style look, don’t wear these boots with a suit because these ARE NOT DRESS BOOTS.
I love the pebbled brown leather and goodyear welting of the Purdey boots above, which is why they’re my top choice. Trust me, I spent a lot of time finding the best boots out there and these are hands down my favorite.
If you want to know how to tie your boots properly like this so don’t have a bunch of excess laces flopping around, check out my video about how to properly tie men’s shoelaces.
Designer Options
Crockett And Jones Galway 2 Apron-Toe Boot
John Lobb Alder Boots
Frye Jones Lace Up Boots
Red Wing for Brooks Brothers 4556 Iron Ranger Boots
