The Men's Guide to Casual Weekend Footwear

The Men's Guide to Casual Weekend Footwear

The workweek is done! You are finally out of the office and ready to relax into the weekend. You have a couple of get-togethers planned, but they will be laid-back and promise to be a good time. You know you don't have to get dressed up, but you still want to look good. In terms of shoes, the oxfords are clearly out of the picture. But what is appropriately casual footwear (especially during the heat of summer)?

You don't want to dress formally, but you still want to be stylish. What to do? Here are different kinds of casual footwear and outfits to pair them with so that men can go into their weekend with both taste and chill.


Let's start with the ones everyone knows. Flip-flops function best when you are going to a place where you will probably be surreptitiously slipping them off at some point. Easy examples are beach barbecues and beach bonfires. You don't go to these events barefoot, but there's still the possibility of a quick beach volleyball game in the sunset or an evening walk on the sandy shore. Having the freedom to be quickly shod or shoeless gives you the flexibility to engage with whatever the evening brings. Plus, if your SAND-als get a little sandy, it's no big deal.

Great outfits for flip-flops include most any shorts combo. Flip-flops pair well with several outfits, from swim trunks, a t-shirt, and sunglasses to a white collared shirt rolled to the elbow, khaki shorts, and a Panama hat. But remember: flip-flops are very informal. So unless you are in Southern California or Hawaii, keep them to waterside events. And probably choose brown or black for the color.


The shoe everyone knows but doesn't know the name of, the most well-known espadrilles are Toms. They have a flat sole with a single piece of material around the heel and another piece wrapped perpendicular to the first around the toe. They almost look like slippers. Able to be easily slipped on and comfortable, espadrilles, like flip-flops, are good options for beach footwear. However, these shoes are a step up from flip-flops and are a bit more flexible in terms of occasion and outfit.

Espadrilles can be paired with pretty much any flip-flop outfit. T-shirts and lounge pants or Hawaiian shirts and shorts could be good with espadrilles. If everything fits well and the colors tie together, it will keep these outfits from looking too relaxed. These shoes can also work with slightly more formal ensembles. Cuffed white chinos with a navy polo or jeans with a white t-shirt and navy blazer look sharp yet casual with a pair of navy espadrilles.

They also complete an outfit of shorts and a long-sleeved collared shirt with aviator sunglasses. Sticking to neutral-colored espadrilles gives you flexibility in your outfit combinations, but these do come in all colors, and if you have enough closet space, a brighter color might be a fun way to spice things up.


Another shoe every man probably has in his closet but normally reserves for either working out or walking the amusement park. Those who walk a lot for their jobs may also rely on sneakers to help their feet survive the workday. But we are talking about casual wear, and sneakers work well for this category. Sneakers, depending on color and material, may even be able to go beyond functional and be a fashion asset. White leather sneakers are the perfect match for all kinds of jeans. Combine them with a white t-shirt and leather jacket, and you have a perfect outfit for an outdoor concert on a cool summer night. Switch to a cream polo on top, and you get a nice party look. This is another shoe you can wear with the t-shirt and blazer combo for a laid-back, suave style. Combining khaki chinos with a navy short-sleeved collared shirt takes things up a notch if you are looking for something a little more sophisticated.

If white is not your thing (the color does need a bit of upkeep and cleaning), something in brown could be a good move. A navy top with a brown blazer could be a good match there. Canvas sneakers are a little more casual than the leather but function about the same in terms of outfits. Since they tend to be a bit cheaper, especially if you find a good deal, you may feel freer to play hard. Just don't forget your socks!

These are the basic casual shoes for guys, though driving moccasins and boat shoes are also worth exploring. Even loafers are considered the gentleman's casual shoe if your wardrobe runs a little more classic and high-end. Ultimately, it depends on you, your style, and what you find comfortable. That's the point of "casual" in the first place, right?


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