2 Timberland PRO Men’s Titan Waterproof 6″ Alloy Safety Toe.1 Thorogood Men’s American Heritage 6″ Moc Toe, MAXwear Wedge Safety Toe Boot.If all the other guys are wearing thick Adidas flip flops or those Quicksilver thong slides, then the guy who’s wearing a nice leather pair will look a lot more put together. Since they’re really more of a practical shoe, going with rubber versions is a safe bet, especially since they hold up well to water. On a hot summer night, you can get away with wearing a nice pair of leather sandals to a casual dinner on a patio.īut flip flops are really only appropriate when you’re lounging by the pool or on the beach, and want something you can easily slide your feet in and out of in between dips in the water. Sandals are already the most casual type of shoe you can wear, and flip flops are the most casual subset of sandals, which means there are really only a small handful of situations in which they’re appropriate. Last but not least, flip flops are the most relaxed type of shoe you can wear with shorts, because they’re barely shoes at all. Second, if your sandals have covered toes, they’re not sandals: they’re shitty shoes.Įither commit to the toe-exposing freedom of sandals, or pick up a pair of the espadrilles listed above. If you’re old enough to read this sentence, you’re too damn old for velcro. In my opinion, the best thing to do is split the difference, and look for a pair of leather sandals with a comfortably padded foot base.Īdditionally, there are two other crucial rules of thumb for sandal-buying:įirst, never, under any circumstances, buy sandals with velcro on them. Unfortunately, many guys find themselves drawn to the latter, which are comfortable, but not much to look at. The various styles of men’s sandals on the market range from the refined, sophisticated and European-looking strappy sandals made of high-quality leather, to the thick, rubber kind that could best be described as “sports luxe.” Making sandals look sharp is notoriously tricky, partly because there are so many damn options to choose from. Of all the different styles of shoes on this list, none are as casual as sandals – and none are as difficult to get right. (Personally I’m on the fence.)īut even those who like the look would have to concede that it gives off a darker and more rugged vibe, which is more appropriate for fall than for warm weather. If you’re wearing black shorts, make sure you pair them with black shoes, never brown.Ĭombining black and brown is one of the most controversial looks in menswear – some say you should never do it, others say it’s totally doable. You can get away with a cap toe, but a full brogue or even a quarter brogue is a little too rugged for this look, as are the sort of chunky-soled shoes you’d wear in fall and winter. Second, opt for flat shoes that have sleek leather uppers, like the models listed below. In this case, the right style of shorts will have a slimmer fit and come in neutral colors, while the shirt should be either a slim-fitting dress shirt or a crisp, stylish polo that’s well fitted to your body type. ![]() ![]() There are two keys to pairing dress shoes with shorts.įirst, since dress shoes are among the most refined styles of shoes, you want to make sure that you choose the right shorts and shirt to complement them. ![]() In this post I’ll break down the types of shoes that look the sharpest, and share a few of the most affordable, stylish and all around best shoes to wear with shorts.Ī good pair of leather dress shoes allows you to push the style envelope even further than penny loafers, and achieve a more sophisticated and even elegant look. Plus, the best way to make a pair of shorts look sharp is to go sockless or wear no show socks, both of which limit the type of shoe you can get away with.īut while pairing your favorite shorts with the right pair of shoes can be tricky, it’s far from impossible. Since there’s nothing but leg hair between your knees and your feet, your shoes are a lot more noticeable, which increases their impact on your overall look. I like to say that shoes are the secret weapon of style, but when you’re wearing shorts that secret – much like your bare legs – is very much out: There’s arguably no piece of men’s clothing that’s more breathable, laid back or easy to wear than a good pair of shorts.īut while they certainly feel great, it can be surprisingly difficult to pair shorts with the right shoes. It doesn’t take a genius to understand why guys would want to find the best shoes to wear with shorts.
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