4 Versatile Leather Shoes Every Man Should Own

Shoes are the foundation of any outfit. The right shoe has the power to enhance your outfit or completely kill it. And seeing as you spend most of your waking life wearing shoes, it’s important to shop for well-made ones that will last a long time. Your best bet at a long-lasting pair is purchasing ones made of leather. These four pairs might cost some cash up front, but you’ll save money in the long run because they last forever. As an added bonus, you’ll likely be able to downsize your shoe wardrobe because these shoes will look great with everything.

1. Brown (mid-brown to dark brown) brogues

brogues from John Lewis

Classic brogues | John Lewis

Leather brogues were first worn by Irish and Scottish farmers to tromp through bogs in. The word “brogue” is Gaelic for “shoe,” and the perforations on the shoe were originally intended to let muddy water out while you were working outdoors. Today, brogues can work anywhere and go with everything. They are an invaluable smart-casual piece to add to your wardrobe. Consider your ideal brogue-style shoes to be a pair that isn’t too beefy or the toe too round because they won’t be sleek enough to be paired with your standard business suit.

On the other end of the brogue style spectrum, ones that are too slender and pointy won’t work with your more casual attire like jeans. The ideal brogue will have an almond-shaped toe that fits within the smart-casual box perfectly. Just make sure that you also opt for a semi brogue (one with a perforated toe cap but no wings) if you’re looking for the perfect brogue that matches any occasion. And be sure to stick within the brown spectrum — black is too severe for smart-casual.

Get the look: John Lewis Rockport Essential Details 2 Apron Toe Brogues

2. Black Chelsea boots

Chelsea boots

Chelsea boots | All Saints

What can you say about Chelsea boots that hasn’t already been said about them? They’re the perfect boots, and they just happen to match almost every outfit. The slip-on nature of the Chelsea boot makes it much more casual than your usual leather lace-ups. It might be the Beatles association with them as well other rock gods like the Rolling Stones of the 1960s, but there is something that is eternally rock ‘n’ roll about the plain black leather Chelsea boots.

Smack in the middle of casual and formalwear, the black leather fabric will make them dressy enough to pair with a suit as well as your favorite pair of slim-fitting jeans. Leather Chelsea boots, as opposed to suede, will stand up to the elements and are easier to remain intact. To maintain a look that is both casual and formal, choose ones that are not too heavy and not too pointy. Wearing them with your jeans stacked like Kanye’s is a perfect casual look, but don’t try to wear your suit pants in that manner. Although you can pair them with a suit (one that might be slightly less formal), do not wear them with a four-button suit.

Get the look: Trist Chelsea Boot by All Saints

3. Minimal white trainers

white trainers

Sneakers | Mr Porter

As of late, sneakers seem to match with almost any outfit, but it’s that perfect pair of minimal white trainers that truly match almost anything, just as long as you keep them clean. The cleaner the sneaker, the better it pairs with a suit — as long as the pants are tailored a little shorter, hitting right below the ankle. The texture of the white trainer is very important in where it falls on the casual-formal spectrum: The rougher the texture, generally speaking, the more informal, while smooth fabrics make the sneaker a dressier option.

Leather trainers are also chunkier, which help to balance out the top-heaviness of tailored clothing or bulkier jackets like an on-trend shearling bomber or even a hefty parka for the cold season. All of this lends itself to sheer versatility.

Get the look: Original Achilles Leather Sneakers by Common Projects

4. Dark loafers

dark loafers

Penny loafers | Cole Haan

Loafers are a smart-casual lifesaver. The loafer style is a descendant of a moccasin-style shoe worn by Norwegian fisherman. The shoes became a mainstay of Ivy League students because of their appeal of falling perfectly between being smart and casual. When looking for that perfect pair of loafers, a rounder toe loafer skews more casual, while one with a sharper silhouette works well with more formal attire.

Make sure to also keep in mind the vamp, which is the top bit of leather that goes from your toe up to your foot — if it’s too short or low then you’ll be showing way too much sock to keep it to formalwear.

Get the look: Cole Haan Men’s Pinch Grand Penny Loafer