There are times I feel trapped by men's clothing. It feels sometimes like my options are, 1.) an imitation of the Brawny paper towel man 2.) a skater pining for the good-ole-days of 2004, or 3.) a retiree who wears primarily golf shorts and pleated khakis. Of course, there are other options than these, but if you are on a budget and don't want to commit a ton of time to meticulously curating your wardrobe, its easy to feel like you are working against your clothes choices rather than embracing them.
Nothing is as scary as men's clothing in the summertime. In the summer, everything is more brash, more colorful, more dramatically what it is. Skater shorts now come with embroidered dragons, and the golf shirts are somehow incandescently shiny and metallic.
And shoes. Ooph. Shoes are the worst. Because when it is hot and humid, having feet that are sweaty and uncomfortable is particular kind of awful. And if you are looking to be comfortable without completely foregoing a sense of style and taste, shoes can be a minefield. So, with that in mind, here's my take on how to navigate summertime footwear.
1. The appropriateness of flipflops is entirely dependent on two factors: foot condition and venue.
I grew up in South Florida where flipflop couture reigns supreme. In Florida you can wear flipflops to the grocery store, and to the beach, and to the mall and even to church. Reefs like these are the classic "go to" for flipflop formal wear in the Sunshine State. I think flipflops are a phenomenon of mob rule: once enough people are okay wearing them to a certain place, its okay. But what is NEVER okay with flipflops is wearing them with nasty, ungroomed, unkempt feet. Its a veritable social obligation––if you are going to let your feet into the world, they need to be clean, odor-free, with trimmed nails and nothing gross or out of place.
2. Wearing shorts? Only go sock-less in shoes that go with socks when you're in pants.
I think going sock-less* with shoes is an intentional variation on a pair of shoes. Think of a classic shoe/sock pairing, like a pair of low-top Chuck Taylor's with stripped ankle socks. Its a look that belongs underneath jeans (outside of gym class in 1988.) But those same shoes can be switched up with a sock-less look when you're wearing shorts. Same thing with a pair of Vans you might normally wear under pants with an ankle sock. Shoes that are shoes, but which you are not supposed to wear with socks (see #3 below; also Crocs) are, in my opinion, best avoided.
*If your feet sweat more than average, going sock-less might not be an option. You don't have to miss out on the look - pair your footwear with no-show socks, like these.
3. Just say no to boat shoes.
Maybe this is a personal hangup, but I don't think the semi-popular, flat and very low shoe works for anyone stylistically. At the very BEST you are going to manage to look like a high-octane rich kid. And its possible to fall into lazy, alcoholic retiree if you aren't careful. They are the golf shirt of shoes.
4. Only wear boots with shorts if you're going on a hike.
If you are specifically trying to channel an early 90's aesthetic with the flannels and the slashed jeans and chain wallet, boots with shorts makes sense. But if you aren't specifically going for that, I think there's no venue for boots with shorts unless the trees there outnumber the people. In fact, anything high-top with shorts is playing with fire.
5. Allow your footwear to lighten up with the rest of your clothes!
On the more intentional side of things, Summer is a perfect time to allow your shoes to break out of standard earth tones or dark, muted colors. So, if that's you, now is a time to maybe go with something creative and colorful, or at least experiment with something lighter in tone. Consider a saddle shoe or a low-top chukka to go with a lightweight pant (Wearing these with shorts is an advanced move that goes along with a fairly ironic aesthetic––not something to try unless you are committed to a whole tongue-in-cheek wardrobe).
6. If you are going to wear full-footed sandals, you better embrace the whole look.
Sometimes a shoe pairing isn't wrong, it just entails a whole look that you can't pick and choose from. And in the Summertime, there are a few styles of full-footed sandals that have become pretty popular. These skirt the boundary between shoes and sandals, but also are most at home in a style that fits with the Eddie Bauer Summer collection. And I note that because these are shoes that can go with that look, but will look just plain weird when not paired with a canvas belt and a windbreaker vest. So, you can go with these, but they come with a whole set of wardrobe assumptions.
7. Own the right kind of socks.
Not all heat should be beaten by disrobing. Sometimes it's a matter of having the right socks. Specifically, athletic, moisture-wicking socks, like these ASICS, can just become an everyday garment rather than being reserved for running. Some of these design features are now showing up in dress socks and other kinds of foot wear that can help you manage the heat without going au natural.