The best men’s shoes for every occasion and every style

Shoes are the conduit between us and the ground we walk on. They keep us connected with the earth and also have the ability to make or break any outfit. From rugged boots to sleek drivers and stylish sneakers to beach-appropriate flip-flops. The right shoes are one of the most essential items in your wardrobe.

While the shoe industry has a wide variety of options to choose from, each one of those options has an overwhelming number of selections. Of course, you can always count on us to compile a list of the best of the best. Here are the best men’s shoes for every occasion.

Tecovas Chance Chelsea Boots

Trying to embody the style and coolness of 60s-era London with the manliness of John Wayne by blending both old-school Western appeal and sleek, modern style, these Chelsea boots are a perfectly rugged hybrid, ready for the open road or a city speakeasy.

Tecovas Chance Chelsea Boots

Thursday Boots Cavalier Boots

Don’t be afraid of the lighter suede. These feature a “WeatherSafe” suede upper that will actually get better and look ruggedly seasoned with age. Thursday Boots are known for high quality and style without looking too stuffy.

Thursday Boots Cavalier Boots

R.M. Williams Classic RM Leather Chelsea Boots

As the brand’s most timeless design, these deep brown leather boots are any city dweller’s dream. The deep brown goes with almost anything, and the soft leather will keep your comfort levels high.

R.M. Williams Classic RM Leather Chelsea Boots

LEMS Trailhead Sneakers

While some hiking boots can be clunky, LEMS has taken the feel of hiking boots and incorporated that technology into low-profile sneakers that you can even wear off the trail. Engineered to give you spring in your step with added traction, we also love the retro-style color options available right now.

Danner Mountain 600 Hiking Boots

Leave it to Danner to take hiking to the next level with these comfortable boots that feature Vibram technology and construction that have more in common with your favorite sneakers than with the clunky hiking boots of days gone.

Danner Mountain 600 Hiking Boots

Beckett Simonon Geller Trainers

Low Top Sneakers to Dress Up

With the elegance of formal dress shoes and the comfort of everyday sneakers, the Geller Trainers from Beckett Simonon are buttery soft leather sneakers that look just as good with jeans as they do with a sport coat and chinos.

Beckett Simonon Geller Trainers

Low Top Sneakers to Dress Up

Veja Esplar Shoes

Veja makes the perfect white sneaker, subtly showing its logo. Feel proud to rock the “V” because this positive impact brand is completely transparent on what goes on in the shoe industry. By spotlighting this, the brand is encouraging the use of sustainable materials, ethical factories, and fairer wages. Veja means “look” in Portuguese, as the brand aims for their consumer to look beyond just footwear.

Greats Royale Sneakers

A minimalist favorite, these versatile sneakers are made with ultra-soft cowhide leather. The more you wear, the better they get. You can wear these with anything in your closet and get away with it. Just remember to wear no-show socks!

La Canadienne Louis

With all the looks you can pull together with the many different sneakers on the market, the one thing you start to lose is individuality. They all start to feel the same. That is where the Louis from La Canadienne comes in. The sleek look of these sneakers with the elegant suede upgrades your sneaker wardrobe immediately.

Mobs Design Tread Low

For the guy afraid to wear all-white sneakers but still seeking a dress-up comfort option, opt for the same vibe in color. Mobs Design makes sneakers that naturally become your go-to because of their comfort and breathability while keeping that cool guy aesthetic. If you’re not into the cognac, don’t worry; they carry many colors.

Vans Old Skool

The Dress Down Sneaker

For the days you’re afraid you might scuff up your “dress-up sneaker,” you’ll need a pair you are more comfortable getting down and dirty with. A dress-down shoe should be hip yet comfortable enough to skate and walk around. Take a look at some of the best sneaker brands should you want more options for your next pair of sneaks.

Your pants-to-shoe ratio will always be acceptable when rocking the Old Skool skater shoe from Vans. Pro-tip: You don’t actually have to be a skater to wear these. The Vans lifestyle encompasses a laid-back and casual California attitude.

Vans Old Skool

The Dress Down Sneaker

PF Flyers Center Hi

If you want something classic, something that never goes out of style, and something that was integral to our generation, the PF Flyer are the shoes for you. Simple canvas with a vintage look, these are the same shoes that Benny “The Jet” Rodriguez used to best the beast. Can’t get any more iconic than The Sandlot

Nike Killshot 2

Nike’s Killshot 2 sneakers mix leather and suede for a play on texture and sheen. They are inspired by the brand’s original tennis shoe, with the classic Nike logo and typeface on the back as an ode to sporty nostalgia.

York Athletics MFG The Frank Half & Half

Between the leather and the mesh, these sneakers are the perfect marriage between an athletic and a lifestyle sneaker. They are made to work out but look great for hanging out. This small brand out of Boston is onto something. Consider yourself warned; these sneakers will attract compliments from strangers.

York Athletics MFG The Frank Half & Half

AllBirds Men’s Tree Dashers

The latest release from AllBirds is the Tree Dasher style, partially made from eucalyptus pulp to ensure a cooling effect with each wear. Made to run, sprint, walk, and hop, the Dasher is super technical, sustainably produced, and beautifully designed.

AllBirds Men’s Tree Dashers

Allen Edmonds Randolph Penny Loafer

The Loafer

Loafers give off a calm, cool, collected, understated elegance. Many guys are intimidated by the tassels or the shine of a loafer, but you shouldn’t be! The second you put on a pair of great loafers, you will feel (and look) like a million bucks. If you’re not quite ready to channel Lord Disick and take the leap to the tassels, there are plenty of other options to achieve the same style mood more subtly.

The good folks at Allen Edmonds go the extra mile with super-sharp dress shoes of all sorts, including these classic penny loafers. They’re ideal for wearing with a suit or tailored chinos.

Allen Edmonds Randolph Penny Loafer

The Loafer

M.Gemi The Filare Loafers

The classic penny loafer got an upgrade with this (literally) modern twist. The twisted band where you usually find a buckle or tassels is subtle and sleek. It’s an all-in-the-details type of shoe, unique enough to make you one. All M.Gemi shoes are handmade in Campania, Italy, and you can smell and feel the quality with each wear.

M.Gemi The Filare Loafers

Astorflex Patnoflex Loafers

Astorflex shows us that loafers don’t have to be as fancy as we thought. If you were intimidated by the above two pairs, opt for a more casual pair like the brand’s Italian-crafted Patnoflex Loafers to match your jeans and button-down.

Astorflex Patnoflex Loafers

Johnston & Murphy Melton Cap Toe Shoes

The Dress Shoe

Whether you like it or not, preparing yourself for special occasions is essential. From oxfords to brogues and Derbys to monk straps, dress shoes come in many shapes and styles. When you’re building a closet of essentials, we recommend staying close to home. Once you create the foundation of your wardrobe with these classics, you can venture out into more.

It’s hard to beat a pair of crisp, sharp brown leather dress shoes, especially when available for under $200. Plus, just because they’re budget-friendly doesn’t mean they’re flimsy or feel cheap. Johnston & Murphy is one of the best in the business.

Johnston & Murphy Melton Cap Toe Shoes

The Dress Shoe

Jack Erwin Clarkson

If you can only afford one pair of dress shoes, you can’t go wrong with Jack Erwin’s all-black cap-toe oxford: The Clarkson. The footwear’s sleek leather finish makes it a go-to pair for formal wear to help you achieve unparalleled sophistication during special occasions. Trust us, that’s one way to put your best foot forward.

Cole Haan Original Grand Short Wingtip Oxfords

Every guy should own a pair of Wingtip Oxfords. In this category, we suggest staying between black and brown leather. Cole Haan should be your go-to for affordable yet high-quality dressy footwear.

Cole Haan Original Grand Short Wingtip Oxfords

Rainbow Sandals

The Sandal

Located in San Clemente, California, somewhere in between Los Angeles and San Diego, Rainbow Sandals encapsulates everything about being a SoCal beachgoer. Of course, they won’t help you stand on a surfboard as the totally awesome waves hit the sand, but the memory foam soles will form to your feet and make you extremely comfortable while you watch others try.

Rainbow Sandals

The Sandal

Birkenstock Arizona Birko-Flor

Once known to be the stereotypical footwear of choice for granola-eating, tree-hugging hippies (hey, we’re here for it!), this sandal has now evolved to become a closet essential for the most fashion-forward of men. We’re happy to live in the middle and advocate for the Arizona Birkenstocks as a stylish upgrade to the pool slide, offering a better-for-you arched footbed and a more durable lifespan. They might feel a bit off at first, but the more you wear them, the more accustomed they become to your own two feet.

Birkenstock Arizona Birko-Flor

Apl Men’s Big Logo TechLoom Slide

One of the most effortless sandals to slip on, these Apl slides are perfect for the pool, beach, and beyond. The best part isn’t how lightweight and packable they are but the fact that they’re made with a flexible strap and molded footbed with every step. They mirror the comfort of the infamous Apl running shoe but are a much breezier option.

Apl Men’s Big Logo TechLoom Slide

To Boot New York Palo Alto Driving Shoes

Trust us when we say that if you’re going to get a driving shoe, you’ve got to go for Italian-made leather… because, well, history! These driving shoes will make you want to buy a vintage Italian car and drive along the coast.

To Boot New York Palo Alto Driving Shoes

Aurelien Light Blue Suede Driving Shoes

Made for leisure and luxury, these ultramarine driving shoes are thoughtfully designed for comfort every step of the way. As the perfect Mediterranean vacation shoes, we recommend pairing Aurelian’s driving shoes with a breathable pair of trousers.

Aurelien Light Blue Suede Driving Shoes

Dr. Martens Black Mono 1460 Boots

The iconic 1460 Leather Lace Up Boots carry great history. Initially made for more comfortable boots during World War II and then made famous for factory workers in the 1960s, these shoes have become a fashion week staple today. Over six decades old, the original Dr. Martens boots remain an ever-popular marriage of fashion and function.

Dr. Martens Black Mono 1460 Boots

Thursday Boots Captain

Every guy needs rugged boots for those moments when they are ready to tackle any of the most arduous manly tasks. From trekking through the wilderness to drinks with the guys, these are the boots that will become a part of your adventure.

Taft Jack Boot in Green Plaid

When you want to stand out, letting your shoes be the loudspeaker for your outfit’s message is a great way to do it. Taft is known for some of the most striking and unique patterns in tis shoes, and its boots are some of the best you will ever wear.

Taft Jack Boot in Green Plaid

Bruno Magli Angiolini

Made by one of the best luxury Italian shoe brands around, these dress boots will bridge the gap between the formal and the casual. They look just as good with a suit as they do with your dress denims. Making these a surefire fit for as go-to boots.

Caring for your shoes

While having a nice shoe collection is ideal, there is a crucial aspect to ensuring that these shoes will last for a long time. Your leather shoes need a good leather protector, and learning how to polish your dress shoes and dress boots will go a long way to making them look great for a long time. The worst possible scenario is spending a good amount of money for a shoe collection, only to watch them go downhill fast.

Do you need 30 pairs of shoes? No. But one from each category is the perfect way to start building a killer shoe wardrobe. With this collection, there won’t be an occasion where you can’t be prepared with the best kicks in the group.

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