Flip-Flops to Boat Shoes: Summer Footwear

by Michael on June 30, 2010 · 6 comments

Shep here is willing to help you find a better use for these. (Photo by pink_fish13)

When the temperature rises, so does the temptation: “man, my feet would feel so much cooler in flip-flops. I’m just going to the bar/store/park/library…c’mon, comfort is important!”

It’s hard to know where to begin, but let’s start here: would you also wear moon boots in the winter?

I didn’t think so. So now that we understand that comfort isn’t the only thing to look for in your footwear, let’s consider your options for staying cool and stylish as the mercury rises:


They were good enough for the natives—plus the natives never created them in as many colors and styles as you have at your disposal.

Minnetonka Men's Moosehide Classic Moccasin

A moccasin has a stitched leather upper, and a sole that can vary from thin leather to fully cushioned with arch support. They’re a more rough-and-rugged version of the loafer. (Or to be accurate, the loafer is a swankier version of the moccasin.)

Wear them in the city, or when driving long distances (“driving moccasins” are great for road trips, but don’t try walking far in them). Moccasins don’t do well in wet places, so they’re not for pool parties or wet grass.

A decent non-designer moccasin will run you $50-$75.

Sperry Top-Sider 2-Eye Boat Shoe

Boat Shoes

A popular choice right now is the boat shoe: similar to a moccasin but with laces and a rubber sole, boat shoes are a great choice for a pool party, sports-bar night with friends, or even boat rides. A boat shoe is normally made to be water-resistant and will always have a non-slip sole, so wet weather isn’t a problem.

Boat shoes also come in a wide variety of colors and patterns, making them slightly more dressy than the utilitarian moccasin. If you’re going with casual pants or jeans and a polo or Hawaiian shirt, go with the boat shoes.

A pair of Sperry Topsiders, the most popular boat shoes, goes for $60-100.

Birkenstock Arizona Sandal


Sandals are your choice if you’re going to be in the dirt or sand or grass—anywhere wet or gritty. The primary purpose of sandals is not to look good (just ask anyone wearing Tevas, or any woman who knows someone who wears Tevas), it’s to basically give your foot support and sole protection, while enabling quick ejection of grit and fast drying.

That said, there are some classy sandal styles out there, and some women who love a guy who exposes his feet. I once dated such a woman, and bought some nice leather slip-on sandals so that she could get her toe fix. When we broke up, I also broke up with those sandals. I now have a pair of functional closed-toe Keen Newport H2 sandals that I bought for walking the beaches in Kauai.

The range of sandals out there is broad: velcro Tevas, neoprene slip-ons, leather, thong…even dress sandals that look suspiciously like regular shoes, only with a few cut-outs. Dressy sandals are hard to wear if you don’t have great fashion sense, so beware. If you’re just looking for comfort, find the most comfortable pair you can—don’t worry about looks, because you won’t be wearing them away from the beach, garden or park, right?

Flip-flops and Crocs

Note that I put these two together. They’re both cheap and worn by guys who just don’t care. Don’t be one of those guys.

Flip-flops are perfect for the changing room at the gym, going to and from the pool or hot tub, and for cheap, disposable beach shoes. They’re not for walking any kind of distance or for going out anywhere with a door or cash register. You can slip on sandals or moccasins almost as easily and you’ll look better.

And Crocs are never right. Plus they get stuck in escalators.

Florsheim Men's Belton Loafer


Finally we look at the dressiest summer shoe, the loafer. Perfect for a casual date or casual work attire, you can wear loafers with or without socks, depending on the occasion, the dress code, and whether you’re willing to funk up your shoes. (Tip: get some extra-low cut socks and no one will be the wiser.)

For evening wear anywhere with a floor, loafers would be the way to go.

To wrap up, try and balance comfort with a little style in your summer footwear. There are plenty of comfortable, cool options that will go with your warm-weather wardrobe.

6 comments… read them below or add one

Cristen July 8, 2010 at 7:16 pm

well why not try the vibram five fingers for that natural foot-look! 🙂


Michael July 8, 2011 at 2:59 pm

I’m saving my pennies for a pair to run in – I wouldn’t call them stylish but they’re very functional for walking in nature, on the beach, or working out.

Zeke July 5, 2011 at 10:54 am

Hey Michael –

In case you don’t live in Southern California, flip-flops are universal footwear here in MOST casual settings (e.g. restaurants, movies, out on the town, beach, etc.). To categorically blacklist them from anyplace but the beach is a fashion faux-pas.

There are flip-flops made of leather & other materials which look great, some can be rather expensive. Most guys I know here have several pairs of flip-flops, some for locker room & beach/pool wear, others for hanging with friends, others for casual dates. Most women here like guys in flip-flops & some have told me flip-flops sometimes serve to make an otherwise intense situation like a first date seem a bit less intense.


Michael July 8, 2011 at 3:54 pm

Yes, Zeke, flip-flops are pretty universal in hot climates. That doesn’t make them stylish, though. (If that were true, Birkenstocks with socks would be Seattle’s similar fashion statement.)

And just to be clear, sandals can be a great addition to the footwear shelf, and I’ve got a great pair of leather sandals that yes, I’ve worn on dates. A good sandal provides support as well. But flip-flops…ubiquitous yes, but stylish…

Nicholas March 13, 2013 at 6:40 am

I agree with Zeke, you’re pretty far off on the flip-flops. Down here in the southern states (I’m from New Orleans, LA, but in Alabama now), flip-flops are stylish and pretty common. Most girls actually like guys wearing flip-flops. Also, sandals get laughed at. Usually called “Jesus shoes”. I’ve thought about getting some boat shoes. Loafers, lol.. This all holds true to today and when this article was written.


Michael March 13, 2013 at 11:40 pm

Hi Nicholas, I understand that many guys feel comfortable in flip-flops and that many guys wear them (and have for decades). And “knowing your audience” is important: you wouldn’t walk into a metal bar with a white sports coat and alligator shoes, or into a swank dance club in a Pantera t-shirt and ripped jeans. There are always going to be subsets of women who like a certain kind of man or clothing. If it takes flip-flops to fit in with a specific crowd, and fitting in is what you want to do, feel free. But that doesn’t make them stylish.

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