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The Ultimate Guide to Leather Shoes for Any Occasion

The Ultimate Guide to Leather Shoes for Any Occasion

19 Jan 2023

The Ultimate Guide to Leather Shoes for Any Occasion

By James Shackell

A good pair of men’s leather shoes can really set the tone for your entire outfit. Think of brown lace-up dress shoes under a sharp suit. Or chunky military boots with slim-fit jeans. Or leather boat shoes with navy shorts and a polo. Each of these shoes sends a certain message. You can picture them in your mind, right? They kind of go together. That’s because certain leather shoes work better for certain occasions. There’s no wrong way to wear men’s leather shoes, exactly, but there are plenty of right ones.

This is our ultimate guide to leather shoes for any occasion. Lace up, and let’s get started.

Leather Care

First things first: a few quick notes on leather care. Men’s leather shoes, even casual leather shoes, are pricey for a reason. If you look after them, and treat them gently, there’s no reason they can’t last for most of your natural life. We’ve written an entire guide to leather polishing, but here are the basics. You should polish your leather shoes every few months or so, depending on wear. Just grab a clean cloth, a 100% horsehair brush, and some good quality leather polish, and start buffing. The more often you do this, the longer your shoes will last.

Suede vs Leather

You might have read about the whole ‘leather vs suede’ debate, but this is a bit misleading. Suede is a type of leather. It’s just got a soft ‘napped’ finish—that raised, slightly fuzzy feeling. Suede is made by sanding the underside of the animal hide, which is softer and more flexible than the outer layer, but way less durable. This is why suede maintenance is so important. All you really need to know is this: polished leather is generally more fancy, and suede is generally more casual.

Dress Code: Formal

Formal is where men’s leather shoes really shine, literally. But contrary to what you may have heard, there’s a whole world of formal leather shoes out there. It’s not just patent leather Oxfords with everything. Penny loafers, Chelsea boots, suede Derbies, fancy monk straps. You should have a good selection of leather shoes in your wardrobe, so you can tailor your feet to every formal occasion.

The Wedding

Weddings and leather shoes go together like open bars and bad dance moves. There are plenty of options here, depending on your suit and the overall wedding vibe. At the top of the range, we have the DYLAN leather dress shoe, hand-made in Tuscany, which is obviously going to complement pretty much anything. But you don’t necessarily have to with go lace-ups. A smart loafer like the ASCOTT or CAVARRA would work nicely, too. Generally with weddings, you want to avoid anything that looks too corporate – whether that’s your 9–5 work suit, or your standard black Oxfords. A little extra effort, and a big scoop of personality, goes a long way. (Hello, DWAYNE monk straps…)

The Black Tie Event

Black tie is by far the most restrictive dress code, so this isn’t the time to mess around. You’ll usually be wearing a tux to these events, so you need proper formal footwear to go with it. This usually takes the form of black, high-shine, patent leather dress shoes, like the HADLEY. These guys are formal enough for greeting foreign dignitaries, so they should see you through a dinner party. If you want to branch out a little, try some patent leather loafers like the ALBERTO or the ASCOTT. The only exception to the black leather rule is velvet, which is quite rare, and incredibly delicate, but can really kick your black tie up a notch. Our black velvet ASCOTT loafers are the way to go here.

Dress Code: Smart Casual

What is ‘smart casual’ anyway? We’ve actually answered that question in detail, but the short version is: ‘smart casual’ is more a state of mind. It’s an umbrella term for (as Mr Porter famously said) “anything smarter than a tracksuit but less formal than a suit”. So you’ve got a lot of room to play here. Leather sneakers, Chelsea boots, espadrilles, Chukka boots, driving shoes, boat shoes – they’re all part of the ‘smart casual’ family tree. It all depends on your styling.

The Office

Let’s start with the easy one – leather shoes in the office. This is what most guys picture when they think of men’s leather shoes: some high-shine Oxfords underneath a three-piece suit. And this is definitely one way to go. The technical term you’re looking for here is ‘business casual’, which is like ‘smart casual’ with spreadsheets. Our BENNET brogues are no-brainers for office-wear. But don’t be afraid to get creative either. A well-heeled leather Chelsea boot, like the BRONSON, is a great alternative to traditional Brogues or dress shoes. Just make sure to keep it black, or dark brown, with a slim line and chiselled toe.

The Cocktail Party

Most cocktail invites are going to be ‘semi formal’ or ‘smart casual’ (a ‘casual’ cocktail party is basically code for ‘we have a keg, come over whenever you want’). There are a few ways to go here, depending on how formal you want to take it. Cocktail parties are a great excuse to bust out some brogues: something like the BENNET or the BRENNIN with dress chinos and a suit jacket will look fantastic. Alternatively, loafers are going to be your best friend here. Try either a tassel loafer, like the ALBERTO, or a simple penny loafer, like the FERNANDO. When styling these guys, just remember to cuff your pants and show some ankle, especially if the weather’s warm.

Dress Code: Casual

This is your most flexible dress code. It’s almost code for: wear whatever you want. But we still recommend putting some thought into your casual outfits. It’s easy to slob around in old sneakers and poorly fitting jeans, but with some small footwear adjustments, even your casual clothes can look smart and put-together. The casual shoes you’re looking for here are low-top leather sneakers, espadrilles, boat shoes, driving shoes, Chukka bots and Chelsea boots.

The Beach

For a day at the beach, you want something light, breathable and easy to slip on and off. That probably means no chukka boots, no Chelsea boots, and definitely no derby shoes. There are two ways we like to go here. You can either whack on some very comfy espadrilles, with their light woven soles, or you can wear leather boat shoes. Boat shoes, like the HATCH, are going to look slightly more formal, while espadrilles with some cuffed jeans and a linen shirt are your classic, laid-back beach look. There’s also a whole family of slip-on shoes to explore, so don’t be afraid to try something more daring, like the TREY or the COSTA.

The Roadtrip

Let’s be honest, your mates aren’t going to care what’s on your feet. But that doesn’t mean you can’t look good on a road trip. For summer drives down the coast, we recommend something light and relaxed, like leather driving shoes or moccasins. For those winter trips into the mountains, you’re going to need something more sturdy. Leather military boots, like the MASSIMO, can survive a quick jog across lava (don’t test us on that, just a figure of speech), or you can go with something slightly more snazzy, like leather Chelsea boots or suede Chukkas. Just throw on some dark denim and a big jacket, and you’re ready to roll.

The Pub

There are two schools of thought when it comes to leather pub shoes. One is substance, the other is style. It sort of depends what pub vibes you’re aiming for. Sticky floor and a cold pint of XXXX? Go with some no-nonsense DECLAN taupe chukka boots and slim-fit jeans. You’ll blend right in. Gastro pub with chargrilled octopus on the bar menu? You want a smart leather ankle boot or high-topped suede Chelsea. Outdoor beer garden with the tunes pumping? Maybe a sharp leather sneaker, like the DECO. If in doubt, check everyone else’s ankles and go from there.