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It’s just a fact that most of us dress very casually more often than we used to, especially when the warm weather arrives. Here are a few footwear ideas that work with your most casual attire. All of these are great without socks and work best with jeans, washed chinos and Bermuda shorts.
This has been around and is probably considered by some to be too much of a preppy icon to be taken seriously. In fact, it still looks right with khakis or Bermudas, it’s comfortable and quite durable. Timeless.
Originally introduced in 1968 as an indoor soccer shoe, the style has made a comeback as a casual, sporty shoe rather than an actual athletic shoe. It doesn’t have the support of the current sport shoes, but it looks so cool and comes in a lot of fun colors. With a pair of beige chinos and a nice tee shirt, it makes you look like you’re wearing exactly what you feel like wearing.
I had my first pair when I was ten. These are pretty retro and probably more cute than handsome, but they’re one of the honest to goodness classic canvas sneakers that will never go away. Converse, of course, also makes Chuck Taylors. They’re great, but the Jack Purcells have a bit more of a “born to it” look.
I know that Vans have a bit of a young skateboarder rep, but they also embody that southern California cool that the rest of us envy so much. My son just ruins his as fast as he can, considers them perfect for blizzard conditions and buys a replacement in the next size up. If I could only get Charlie to buy black rather than white. For the rest of us, they’re easy and casual and we can at least imagine that we look younger when we’re wearing them.
This is a nice version of a style that’s offered by a number of shoe brands. It’s basically a Stan Smith without the perforations made in a menswear color. Again, a sporty shoe, not a sports shoe, it’s not quite as casual as most of the others featured here, but it’s a neat style when you’re just a bit more dressed up. I think it’s great with pants, but, in this color, not so great with shorts.
This is a borderline sloppy beach bum shoe, but it’s got just enough style and structure to make the list. Definitely meant for kicking around and not for going out to dinner. It’s made of synthetic mesh, so it’s cozy and dries fast.
This is another timeless classic, but I like it a lot better in the sand-washed version than in plain white or navy. Sort of interchangeable with the Vans slip-on, but with a bit more yacht club cred.
These come in rubber as well as leather. A while after I bought my first pair, I was sitting on the beach and noticed a metal thing embedded in the sole. After a moment, I thought, “Wow, somebody was thinking. I have a bottle opener on the bottom of my flip flop.” A lot of companies make similar styles, but Reefs are really comfortable and then there’s that cold Modelo Especial that needs to be opened.
This is one of the last of the genuine Maine hand sewn shoe brands. This particular style combines a rugged, casual look with some contemporary refinement. This pair is in the classic dark brown, but it also comes in a nice saddle tan. They’re built like tanks and give the perfect touch to your favorite khaki pants or jeans. They can certainly be worn with Bermudas, but they’re a bit too much of a real shoe for me to wear with shorts.
This is a pretty innovative brand. This shoe is made of some kind of synthetic rubber. It has a mesh liner and slots through which water can drain. This has a ritzier looks than most of the others here, so it’s probably the only one that you’d wear with a jacket, but it’s seriously practical and the only thing you need to care for it properly is a garden hose. Cool.
I saved my favorite canvas sneaker for the last spot. The company started in Italy in 1911 and introduced this style in 1925. I didn’t discover it until sometime after that, but I never looked back. To my eye, it has the perfect look. They really hold up and they come in a bunch of colors, some of which I wouldn’t be caught dead in. I featured the yellow ones for fun, but my current pair is navy. The ivory is really nice and less stark than pure white, which is the one which probably outsells all the others.
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