I used to believe that a man could never have too many shoes. It wasn’t until I got married and had a kid that I was served a hearty portion of humble pie. Though, if truth be told, I wish I’d realized sooner.

Even if you’re not fighting for wardrobe space, streamlining your shoe collection is transformative. Not only will you be better off financially, but you’re left with a selection of styles that you’re actually going to wear.

Keep reading as I round up the men’s shoes that go with everything. From sneakers and loafers to boots and Derbies, these are the essential options that every guy should invest in.

Key Takeaways

Choice is a good thing, but too much can quickly become overwhelming. As I get older, I’ve grown to realize, and begrudgingly accept, that instead of hanging onto footwear that I’ll likely never wear, it’s far better to have a smaller selection of the best men’s shoes that go with everything.

To help you face the music, too, I’ve been on a one-man mission to create a definitive list of the styles that no collection should be without. After mourning my Mihara Yasuhiros and grieving for Guccis, I’ve pored over hundreds of ratings, reviews, and Reddit forums to bring together every shoe, sneaker, and boot worthy of your consideration.

Here, you’ll find the most comfy, versatile, and low-maintenance designs on the market, including Oliver Cabell’s loafers and Myrqvist’s Derbies.

Why it’s great: Forget transient trends and fading fashions; Oliver Cabell’s loafers are for life. The ideal blend of smart and casual, these do-it-all shoes can be dressed up or down with ease; you can wear them when you’re heading into the office or grabbing a bite to eat with friends.

Inspired by the old-school Ivy style that’s as popular now as it was when your grandpa went to college, they’re made from full grain calf leather using hand stitch construction that makes them super tough.

Who is this for? I’m not joking when I say these are the best men’s shoes that go with everything. Looking just as good in the summer with shorts and a linen shirt as they do in winter with a turtleneck and suit, they’re comfortable and durable and simply refuse to go out of style. Don’t forget to pack them before your next travels.

Flaws but not deal-breakers: These are men’s shoes that go with everything. Know, though, that you may have to push through a breaking-in period if you have particularly wide feet.

Material: 100% Leather | Sole Material: 100% Leather | Sizes Available: 6–14 | Colors Available: 5 | Style: Loafers

Why it’s great: Of all the casual dress shoes, the Derby is the most resourceful. Characterized by its sturdy sole and open lacing, it’s the most stylish solution to your footwear facers, whether you need smart but comfortable shoes for work or something more refined than a tasseled loafer.

My go-to pair of Derby men’s shoes that go with everything is from Myrqvist. Boasting a beautifully textured calf leather upper with a double-layered studded rubber sole, it’s a jack of all trades that’ll tackle any weather, outfit, or occasion.

Who is this for? If you’re looking for smart, but not too smart, men’s shoes that go with everything, Derbies are a game changer. Wear them with your suit for formal events, or dress them down with jeans or chinos.

Flaws but not deal-breakers: The sturdiness of these shoes means that they can take a few wears to properly soften up.

Material: 100% Leather | Sole Material: 100% Rubber | Sizes Available: 8.5–12.5 | Colors Available: 2 | Style: Derby

Why it’s great: Every wardrobe needs a pair of white sneakers, if only for one simple reason: They can be worn with literally anything. Unfailingly versatile and uber-clean, the timeless, fuss-free design is your saving grace when you’re struggling to decide what to wear.

Need something to dress down a suit? Try white sneakers. I’m not sure if your espadrilles look quite right with linen pants. White sneakers will. And what about a replacement for your beat-up old kicks? You get the gist. And this leather pair from Aurelien couldn’t get any better.

Who is this for? A fail-safe option that can lend itself to any outfit, these Aurelien sneakers are a luxury take on a footwear Hall of Famer. Warning: You’ll need to splurge, but they’re a great investment piece that you’ll be wearing all year round.

Flaws but not deal-breakers: Yes, these are men’s shoes that go with everything. However, the price tag is hard to swallow. Fear not: I’ve compared the cost with investment return, and you’re in good hands (or should I say feet).

Material: 100% Leather | Sole Material: 100% Rubber | Sizes Available: 6–14 | Colors Available: 7 | Style: Sneakers

Why it’s great: They’re handsome (in a Tom Hardy way), tough, and easy to style, so it’s no wonder that Chelsea boots have been the footwear of choice for everyone from rock stars to royals. I guess it also helps that they’re the type of shoes that go with everything. Velasca’s pair are a work of art; made from soft suede and set on a rubber sole, they’re an excellent year-round option that scoffs at trends and nails both smart and casual dress codes.

Who is this for? Ideal for adding a rebellious edge to your favorite fits, these boots will quickly become one of your most dependable everyday options. You’ve got your pick of pants, but just make sure they’re wide enough to stretch over the top of your boots.

Flaws but not deal-breakers: Like most boots, these can take a few wears before they reach peak comfort. To help speed up the process, simply choose the right socks, ideally something thick for added protection around friction points.

Material: 100% Suede | Sole Material: 100% Rubber | Sizes Available: 5–14 | Colors Available: 2 | Style: Boots

Why it’s great: Vans’ Authentic sneakers have been my go-to budget option for as long as I can remember. Everybody’s favorite beaters, they’ll handle muddy fields, puddled pavements, and sandy shores. More importantly, they’re men’s shoes that go with everything.

Whether you’re into your streetwear, skating gear, or prefer a nautical vibe, these canvas kicks will quietly complement anything you put them with. Heck, you can even wear them to the gym or with casual tailoring.

Who is this for? If you’re on a tight budget or simply want shoes that can handle whatever life throws at them (including heavy frames), then Vans are pretty hard to beat (literally). There’s a reason they’ve been around since the 60s.

Flaws but not deal-breakers: If you’re in between sizes, then go for the larger of the two. I once made the mistake of sizing down, and it felt like my toes had spent the day clamped in a vise.

Material: 100% Canvas | Sole Material: 100% Rubber | Sizes Available: 3.5–10.5 | Colors Available: 4 | Style: Sneakers

Why it’s great: They’re among the most adaptable shoes you can own; there’s a reason brogues stay around season after season. Easy on the eye and kind to your feet, they come in many variations, from Oxford brogues to Derby, and manage to look at home with formal and casual clobber alike.

Arkbird’s pair is handmade from leather and finished with sweat-absorbing OrthoLite insoles that are a godsend when you’ve been standing all day. Amazon customers give them five stars for fit, comfort, and quality.

Who is this for? These men’s shoes that go with everything also happen to be seriously comfortable, so they’re great for guys who spend a lot of time walking around or are on their feet for long periods.

Flaws but not deal-breakers: The overall construction could be improved; but considering the price, they’re much better than they should be.

Material: 100% Leather | Sole Material: 100% Rubber | Sizes Available: 7–13 | Colors Available: 3 | Style: Brogues

Why it’s great: Rich in history and unapologetically awesome, desert boots are proper badass. They manage to perfectly tread the line between fancy and informal, and there’s not an outfit on the planet they can’t improve.

This pair from Tod’s has been on my radar for some time. Crafted from supple suede and set on thick rubber soles, they’re just like the pair that Steve McQueen wears in Bullitt. And who doesn’t want to look like the King of Cool?

Who is this for? Not as dressy as Oxford shoes but smarter than sneakers, these desert boots are the ultimate compromise. Great for everyday wear, they can be styled with everything from tweed jackets and chinos to button-down shirts and jeans.

Flaws but not deal-breakers: These are some of the best shoes that go with everything, but their price tag is enough to dent even the biggest bank balances.

Material: 100% Suede | Sole Material: 100% Rubber | Sizes Available: 8–13 | Colors Available: 1 | Style: Boots

Why it’s great: One of the most iconic shoes ever made, not to mention the most versatile, Converse’s Chuck Taylor started life on the basketball court before going on to achieve its all-star status in the sneaker world. Worn by everyone from Elvis Presley to Timothée Chalamet, they have a shape that is undefeated, a canvas that is breathable, a price that is on point, and a versatility that allows for unlimited styling opportunities. Need I say more?

Who is this for? Who isn’t it for? Chuck Taylors look good on anyone and with anything.  They’re in the stratosphere of the best men’s shoes that go with everything. Bringing a laid-back vibe to both casual and formal fits, you can dress them up with relaxed tailoring or down with sweatpants and a plain white tee. They’re available in regular and wide fit, too.

Flaws but not deal-breakers: Canvas can be harder to clean than other materials like leather, but getting Chucks a little dirty makes them even cooler, if you ask me. It’s also worth mentioning that Converse recommends ordering a half size down.

Material: 100% Canvas | Sole Material: 100% Rubber | Sizes Available: 3–16 | Colors Available: 10+ | Style: Sneakers

Buying Considerations for Men’s Shoes That Go With Everything

Color

Avoid bold patterns or fancy colors, and opt for versatile shoes in black, brown, or navy. These will forever be in favor and can be easily paired with a wide range of outfits for numerous occasions. For sneakers, white is undefeated.

Style

When looking for men’s shoes that go with everything, it’s important to stick to classic designs such as loafers, oxfords, or minimalist sneakers. Although statement styles can quickly become yesterday’s news, these types of shoes will remain stylish and adaptable for years to come.

Material

If you’re buying fewer shoes, then material quality is more important than ever. Make sure to invest in high-quality fabrics such as leather or suede, as they offer the utmost durability and comfort, as well as a timeless appearance that complements various clothing styles.

How We Chose

Having recently cleaned out my closet and updated my own footwear collection, I started my search with fresh enthusiasm and a deep understanding of the best shoes that go with everything.

After drawing up a shortlist of 40 styles, I eventually narrowed them down to eight options judged on the criteria below:

Versatility: I assessed each shoe’s ability to pair well with a wide range of outfits and occasions, from casual jeans to smart slacks. This involved selecting styles with neutral colors and classic designs that could seamlessly transition between different settings. I considered how well each shoe matched with various wardrobe staples and whether it could be dressed up or down.

Comfort: Comfort was a top priority. The best shoes that go with everything should also be suitable for all-day wear. I examined the quality of the insoles, arch support, and overall fit, ensuring that each option provided enough cushioning and support for extended use.

Durability: I prioritized shoes made from quality materials like leather or suede, known for their longevity and resistance to wear and tear; durability was crucial since they would be worn frequently. I evaluated construction, such as stitching and sole attachment, while considering how well the shoes held up over time.

Price: I compared the cost of the shoes to their quality, comfort, and versatility, ensuring that each option provided good value for money. This involved balancing budget-friendly choices with higher-end options and considering whether the durability and style justified the investment.

Why Trust Us?

Billy Webb is not only a footwear fanatic but also an experienced journalist with more than 10 years of experience writing for some of the industry’s biggest publications. His deep passion for shoes and extensive knowledge of fashion makes him a trusted authority in finding the best men’s shoes that go with everything.

Having also worked as a menswear stylist, Billy understands the importance of balancing style, comfort, and versatility, and his keen eye for detail ensures that his recommendations are both practical and timeless.

Final Verdict

Men’s shoes that go with everything are essential to any well-rounded roster, with options like Oliver Cabell’s improving your outfit options tenfold. Impeccably crafted, comfy to wear, and a stylist’s dream, the brand’s loveable loafers should be at the very top of your wish list.

Not only does their sleek design and soft lining make them ideal for all-day wear, but the rich black hue also ensures that they match virtually any color or style in your wardrobe, from gray suits to blue jeans and stolen chinos.

Billy is a content specialist and social media manager. His portfolio includes articles for publications such as British GQ, Esquire and Men’s Health. A self-confessed lover of luxury streetwear, he admits to an unhealthy obsession for baseball caps and high-end sneakers.