The Right Kind Of Leather Shoes For Every Occasion

When to wear brogues, hiking boots, Chelsea boots, loafers, etc.
IMAGE Unsplash/ Anton Darius @theSollers

Chances are your shoe closet consists of racks of different sneakers imaginable and a single pair of leather shoes for every occasion: work, weddings, that job-defining meeting, and all those events labeled as black-tie.

Just as you wouldn’t use the same shoes during a basketball game and a morning run, there are different kinds of leather shoes for every occasion. Here, the right pairs that suit all the events in your life. 

For The Date

Wing-tip brogues by Carmina

Whether it’s the first date or your 10th anniversary, you can’t go wrong with wing-tip brogues with chinos and a button-down shirt, especially if you’re going for dinner and drinks. Don’t let the intricate design, aka the broguing, mislead you; they actually denote a more casual style than plain oxfords. 


Chelsea boots by John Lobb

Otherwise, you can take a page from the Beatles and cop yourself a sleek, sexy pair of Chelsea boots. Worn by different generations, from the mods of ’60s to the grunge crew of the ’90s, the boot has a refined and rock n’ roll appeal at once. These go well with a sport coat and dark denim for, say, a concert or a gallery opening. 

For The Presentation

Cap-toe oxfords by Church's

If you’re closing that all-important deal, let your clothes do (half) the talking for you. Command attention with a classic pair of cap-toe oxfords, a quintessential choice with the work suit. Tip: While you may be tempted to reach out for black oxfords all the time, brown pair best with navy and gray suits. 

For The Hike 

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Work boots by Timberland

Sneakers on a hike? You will fare better in the great outdoors with a sturdy work boot, a staple in workwear. Think of heritage Red Wing boots or Timberland. You can’t go wrong with slip-resistant soles and a steel cap toe when you’re traversing unfamiliar terrain. 

For The Airport

Loafers by Tod's

When you’re about to haul yourself on a 16-hour flight, loafers can actually be your best choice while in transit. Easy to slip on and off, they save a lot of time by skipping the unraveling of shoelaces at security check. They’re also easy to pair with whatever jet-setting outfit you have on.


Desert boots by Clarks

Desert boots are another alternative. Traditionally used by soldiers walking through, well, the desert, its simple look makes it the versatile shoe to wear with all sorts of clothing. They’re also comfortable as hell to walk around in, especially when you’re exploring a new city by foot. 

For The Black-Tie Event

Wholecut oxfords by Gucci

In case the dress codes “black-tie” and “white-tie” confuse you, here’s a quick primer: Both denote a level of formality, with white tie being the most formal, and thus exceedingly rare these days, so most formal events you’ll attend will most likely be a black-tie affair. Think dinner jackets, formal dress shirts, bow ties, and whatever James Bond would wear. For a sharp look, pair your tuxedo or black suit with black wholecut oxfords

For Sundays

Leather sneakers by Greats

Sundays are casual days. Whether you’re spending a sunny day at the mall or walking around the park, the better alternative to white sneakers is a pair of... white leather sneakers. Think Greats Royale court shoes, Common Projects white sneakers, or the fan-favorite Stan Smiths.

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Sam Beltran
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