When it comes to building your unique footwear collection, it’s no secret you should have a variety of options to choose from

Even if you’re a die-hard sneakerhead, you need to have a few other styles in your closet to switch up your look every now and again – after all, while skate shoes or cross-trainers may be your comfortable go-to when it comes to footwear, we’re here to tell you leather shoes can be just as stylish and comfortable as your favorite kicks. 

Leather shoes are definitely an investment worth making, and thankfully, the style isn’t just limited to stuffy dress shoes anymore. From classic trainers and desert boots to boat shoes and sleek, stylish oxfords, there’s something on this list for everyone. No matter what the event, be it a wedding, a night out on the town with your boys, or a casual day in the office, we’ve got you covered with the 10 best leather shoes for all occasions. 


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1. R.M. Williams Craftsman Chelsea Boot


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If you’re looking for a pair of leather boots that’ll stand the test of time, then look no further than the R.M. Williams Craftsman Chelsea Boot. These babies feature elastic side panels for ultimate comfort and flexibility, pull tabs to help you slide them on effortlessly, a square toe for a modern look, and come in two classic colors that’ll surely match any item in your wardrobe: Chestnut Brown and Black. 

These boots also boast a 1.3” heel, come in sizes 4-12, and are made of 100% leather. The best part about the R.M. Williams Craftsman Chelsea Boots is that they’re wildly versatile: you can wear them with your finest suits to give your formal wear an updated, sleek look, or you can pair them with skinny jeans to give your everyday style a classy upgrade. 

2. Tod’s Lace-up Leather Shoes


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Every dude needs a pair of classic, lace-up oxfords in their closet, and Tod’s Lace-up Leather Shoes are a timeless wardrobe staple that belongs in every guy’s shoe arsenal. “Handcrafted from leather using superior artisan techniques,” these faded brown leather kicks are perfect if you’re going for that laid-back yet classy Italian style, and feature a leather sole, branded insole, and of course, are made from 100% leather.

These lace-up shoes also feature an almond toe, a one-inch heel, and can be worn with pretty much any outfit to give it a stylish boost. If you’re feeling really daring, roll up your pants just above your ankles to really show off these classic oxfords – and hey, the weather’s getting warmer anyway, so you might as well try it!

3. Dr. Martens 1461 Leather Derby Shoes


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Is there any shoe that’s more iconic than a pair of Dr. Martens? The brand’s 1461 Leather Derby Shoes have been a staple in the punk scene since the 70s, and nearly half a century later, they’re still in popular demand – and there’s a reason for that. Not only are they stylish and truly stand out in a sea of leather imposters, but they’re also pretty affordable, too.

Complete with a round toe, Dr. Martens’ signature yellow stitching, a stacked heel for a little bit of lift, and simple, three-eyelet lacing, the 1461 Leather Derby Shoes are a must-have for those with a refined punk or grunge style.

4. Timberland Leather Boat Shoes


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This may not be a well-known fact, but you don’t actually have to own a boat to own boat shoes. These Timberland Leather Boat Shoes are perfect for warmer weather and look best with a pair of shorts that hit right above the knee for that laid-back, vacation vibe.

Made from 100% leather, these boat shoes come in a classic medium brown color and boast a round toe, flat rubber sole, leather lining, and front lace-up details. The height of the heel is just under an inch high, so you’ll get a subtle lift while you’re rocking these bad boys on your summer getaway – or just around your local brunch spot. 

5. Birkenstock London Leather Shoes


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When you think “Birkenstock,” the company’s classic, hippie-esque sandals likely spring into mind, but we’re here to tell you Birkenstock has more to offer than just your regular old slip-ons. The Birkenstock London Leather Shoe comes in a Habana brown, features a round toe, suede lining, brass buckle detail across the front, and an outer lining made of 100% calf leather for a comfortable fit.

If you’re looking for a comfy leather shoe that can be worn day in and day out, these puppies should definitely be in your shopping cart ASAP. Wear ‘em with jeans, linen pants, chinos, whatever – they’re incredibly versatile and will add a certain flair to your wardrobe. 


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6. Clarks Desert Trek


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Desert shoes should be a no-brainer when it comes to upping your shoe game, as they’re not only comfortable, they’re super stylish and will give any aesthetic a cool upgrade. Clarks have been around since the 1970s, so if you’re looking for a tried-and-true pair of kicks that’ll last and won’t break the bank, these babies are definitely for you.

Made with Nubuck leather, these desert shoes also feature a “central butt seam and crepe sole” and have over 45 five-star reviews on Clark’s website. The Clarks Desert Trek comes in a variety of colors – light taupe, black suede, beeswax, dark brown, and blue – and is available in sizes 7-13, so you’ll definitely be able to find the right color and size to fit your personal style. 

7. Paul Smith Byron Leather Loafers


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Loafers are one of the most classic silhouettes when it comes to shoes, and the Paul Smith Byron Leather Loafers are some of the best in the game. These mahogany brown, patent-leather loafers can be dressed up or down, but we recommend pairing them with designer denim, khakis, or even wearing them sock-less with shorts in the warmer weather; you can also throw on some chinos and a button-down to class ‘em up.

Made in Italy, the Paul Smith Byron Leather Loafers feature a penny-slot top strap, leather lining, a black rubber trek sole, and come in sizes 6-11.

8. Common Projects Original Leather Trainers


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Every shoe fanatic knows that a classic pair of sneakers is a non-negotiable when it comes to building the ultimate footwear collection, and Common Projects Original Leather Trainers should absolutely be in your shoe rotation. Minimalists will love the classic and sleek all-white leather design, and the “signature gold-tone serial number across the heel” just adds to the simple luxury of these sneakers.

Made in Italy, these shoes also feature a round toe for a classic, casual look, a white rubber sole, and white leather lining. Pair with joggers and a plain white t-shirt for a laid-back but sophisticated street style look or wear them with your favorite pair of fitted jeans for a more classic style. 

9. Red Wing Boots


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If you’re looking for a sturdy leather boot that’ll also show off your cool, rugged style, Red Wing boots are undeniably one of your best options. One of the best things about Red Wings boots is that the more you wear them, the more they mold to your feet – which means over time, they’ll become some of the most comfortable boots you own.

Complete with a traction tread outsole and made from 100% leather, these boots are not only suitable for all-day wear, but they’re also built to last. It’s important to note that most people who’ve purchased these boots usually size a half size to one size down from their normal size, so keep that in mind when you’re buying them.

10. Santoni Double-buckle Leather Shoes


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The Santoni Double-buckle Leather Shoes will undoubtedly make you stand out from the crowd in the best and most luxurious way possible. Made in Italy, these bad boys will offer some serious style to any outfit; whether you’re dressing for a wedding or just a casual night out on town, you really can’t go wrong with these classy shoes.

The almond toe is one of the most flattering shapes around when it comes to leather shoes, and the silver buckle details across the top of the shoe are a minimalist’s dream. The Santoni Double-buckle Leather Shoes also feature a 1.4” heel, so you’ll get a subtle lift when you wear them. 


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