The Best Summer Shoes That Are Actually Longlasting (2026)

Just because it’s summer does not mean your footwear has to be sloppy and disposable. Yes, even flip flops.

But flip flops aren’t your only resort! There’s a wide world of shoes outside of (bad) sneakers and sandals, and they won’t just make your casual summer clothes look more put together.

These are shoes that look better and get more comfortable as you wear them, and they’ll last you for many, many summers. (That means they save you money in the long run, too.)

I’ve worn dozens of boots and shoes, visited factories around the world, and interviewed countless experts in fashion and footwear to help you buy casual, durable footwear that will stay in style year after year. Our philosophy: just because you’re not dressed up doesn’t mean you can’t dress well.

My Favorite Summer Shoes

• The Boot-Shoe: Red Wing Moc Oxford
• Boot-Leather Sneakers: Thursday Heritage Premier Sneakers
• Loafers: Grant Stone
• Sandals: Chamula Cancun Huarache
• Espadrilles: Koio Ostuni
• Turkish Leather Slippers: Sabah Slippers
• Leather Slides: Mohinders City Slipper
• Leather Mules: Luca Drift
• Leather Flip Flops: Southern Polished

The Boot Shoe: Red Wing Moc Oxford

Red Wing Heritage’s Moc Oxford, or “moxford” as I call it, is simply a shoe version of what many have called the most iconic American boot of all time: their Classic Moc.

Far and away the toughest shoe I’ve ever owned, the casual-yet-handsome moxford is the closest I can get to finally, finally being able to wear boots with shorts.

What I liked:

• Durability: This is one of the only shoes you’ll ever find that is exactly as durable and resoleable as a work boot.
• Versatility: Looks great with shorts or with trousers, I’ve personally worn them with everything from fatigues to board shorts to linen chinos. Feel free to keep wearing these all the way through winter.
• Materials: You can choose from four leathers; I like the summer straw colored Abilene, but they also come in the brand’s most famous boot leathers.
• Made in USA: And the leather’s tanned in Minnesota as well.
• Style: Red Wing’s Classic Moc is likely the most influential American boot of all time and has serious crossover appeal for any style. It’s so dope that I can wear it in summer now.

Downsides, but not deal breakers:

• They Feel Like Boots: You might be surprised at how heavy and stiff these “summer shoes” are.
• Break In: Bring spare shoes to change into when these are new; your feet will get sore before the leather softens.
• Price: They’re as durable as Red Wing’s boots, but priced like it; $310 might be tough to swallow.

The Thicc Leather Sneaker: Thursday Premier Sneaker

Thursday Boot Company’s Premier Sneaker combines boot-quality leather with a sneaker’s build — except the sneaker, being both stitched and sewn to the sole, is more durable but just as comfortable as your standard sneak.

I’m not saying that because of the marketing, I’ve worn these myself and they’ve proven far more durable than my Converse All Stars, which start separating at the toe break within a year of purchase.

But the leathers deserve the spotlight because they all come from the world of boots. My own pair are made from the same waterproof waxed flesh that I wore on my Hero boots from Thursday, and there are seven others to choose from.

The Heritage lineup includes Thursday’s two bestselling leathers (Tobacco and Arizona Adobe), several vachettas (a famously soft vegetable tanned number) and the literal most popular boot leather on Earth, Chromexcel.

Another bonus is fit: the Premier comes in wide widths and half sizes, both surprisingly rare options for casual leather sneakers.

What I liked:

• Quality: Not just the boot-ready leathers, these sneakers also stand out for being both stitched and glued to the sole. (Practically every sneaker is just glued, delaminating easily.)
• Durability: The Heritage line has hard-wearing leathers that are known for not just protecting you from the elements, but for looking and feeling better with every wear.
• Variety: There are over twenty leathers available for these sneakers and eight “heritage” boot leathers like Chromexcel, vachetta, and (my) waxed roughout.
• Fit options: Comes in wide widths and half sizes, allowing for a better fit than most leather sneakers.
• Aesthetics: Develops a nice patina over time, especially with leathers like waxed flesh. The use of boot-like eyelets is another way they evoke boots; it’s a cool riff.

Downsides but not deal breakers:

• Break-in period: Boot leather uppers with leather lining and leather insoles means serious long term comfort and durability — but they need time to break in, too. Avoid no show socks until they do.
• Nickel eyelets: This is a reference the sneaker’s boot origins, but you might prefer a more minimalist look.

Durable Loafers: Grant Stone

If you like shoes that are casual, durable, resoleable, and versatile, you need to stop overlooking loafers. A good loafer hits all those notes, but if you prize durability and versatility over, say, dressiness, look no further than Grant Stone.

Well known for their impressive longevity, the Goodyear welted Traveler loafer has become a cult favorite among boot nerds for its excellent quality control versatile design. With its rounded toe and high side walls, the Traveler can just as easily be worn with a suit as it can with shorts.

The loafer has become so popular that Grant Stone put real investment into the lineup: it’s now not only available in three widths, you can get it in about a dozen leathers at any time. Bourbon Suede and Dune Chromexcel are the most popular, but if you’re feeling like pink suede or green kangaroo, they’ve got you covered.

What I liked:

• Versatility: Can be worn casually with t-shirts and shorts, or dressed up to business casual.
• Craftsmanship: These are world renowned for the kind of consistency and quality control that used to be confined to $700+ loafers.
• Great Customer Service: They work with you to nail your size and ship you replacements lightning fast.
• Variety: Brands like Grant Stone offer a huge range of leather options that include pink suede and green kangaroo.

Downsides, not dealbreakers:

• Breaking in: If the loafer’s Goodyear welted, avoid going sockless for the first few wears.
• Price: No one makes them like these for less, but the $400 price point makes some guys squeamish.
• Limited breathability: If the loafer is lined or has a midsole, like Grant Stone’s, it doesn’t breathe as well as unlined Blake stitched loafers.

Superior Sandals: Chamula’s Cancun Huarache

Huaraches are traditional Mexican sandals, typically made with woven leather strands forming the upper part of the shoe. They have a long history dating back to pre-Columbian times.

These Huaraches, made by LUCA (one of Huckberry’s in-house brands), have a braided leather construction that makes for an impressive balance of durable, breathable, and flexible, plus it’ll mold to the shape of your foot over time. The fact that they have a heel means they’re the most breathable summer shoe that’s easy to walk around town in.

What I liked:

• Comfort: Surprisingly comfortable for sockless wear, easy to walk around in for extended periods.
• Versatility: Can be worn with various casual summer outfits.
• Practicality: Includes a heel, improving walkability compared to heel-less slip-ons.
• Breathability: Woven design allows for excellent air circulation, ideal for hot weather.

Downsides, not dealbreakers:

• Old Fashioned Look: The braided leather design might evoke dated “dad” aesthetics.
• Limited style versatility: The distinctive look is probably best for smart casual.
• Potential durability concerns: Woven leather might be more prone to wear than solid leather construction.

The braided leather design might evoke memories of 1980s fashion trends, but the comfort and breathability quickly converted me to a fan. Now I call them “retro” instead of dated.

Espadrilles: Koio Ostuni

Espadrilles offer a middle ground between loafers and slides, providing a low key yet put-together look that’s great for making the most casual outfits level up.

Koio, known for their sneakers, produces a notable espadrille model called the Ostuni. These shoes feature a moc stitch detail that elevates their appearance compared to plain toe slipper-style espadrilles.

Made from suede and unlined, they offer excellent breathability, making them ideal for summer wear. Koio also makes theirs in Catalonia, Spain — the very place the espadrille was invented.

What I liked:

• Comfort: Like a low tech loafer with less structure and a softer sole.
• Convertibility: Wear them as slip ons or stamp on the heel and wear them as slides.
• Versatility: Strikes a balance between the casualness of flip flops and the put-together look of loafers.
• Breathability: Combining suede with an unlined construction allows for good breathability.
• Authenticity: Made in Catalonia, Spain, where espadrilles were invented.

Downsides, not dealbreakers:

• Sizing limitations: A lot of brands don’t offer half sizes, which can be an issue for a perfect fit in laceless shoes.
• Potential durability concerns: Not resoleable and made with natural materials, espadrilles have a reputation for not lasting as long as other entries on this list.

Koio doesn’t offer half sizes for the Ostuni, which is a downside. It’s eco friendly in its emphasis on natural materials, but it’s not resoleable and not the most durable on this list.

Turkish Slippers: Sabah Shoes

Turkish slippers, like those from Sabah, offer an underrated alternative to other slip-on summer shoes. These versatile shoes can be paired with casual outfits like t-shirts or more dressed-up looks with linen button-ups.

What sets Sabah apart is their wide range of leather options, with over two dozen colorways available, including leopard print and roughout leather. I know guys who exclusively wear Sabah in summer, racking up a big collection to bring with any outfit or occasion.

What I liked:

• Practicality: They’re easier to slip on and off than loafers, easier to walk in than slides.
• Versatility: The kind of minimalist that can dress up or down, depending on the leather you choose.
• Quality: These last for years and develop a nice patina as well.
• Color: Sabah offers over two dozen colorways.

Downsides, not dealbreakers:

• Price: There are cheaper Turkish slippers on Etsy.
• Arch Support: There’s better arch support with loafers and even some sneakers.

Leather Slides: Mohinder Woven City Slipper

Leather slides and mules offer easy-to-wear summer options. Mohinders, available on Huckberry, creates hand-woven leather uppers using natural, undyed water buffalo leather.

They’re as traditional and sustainable as a slide can get: the footbed is lined with goat leather, and the sole is natural crepe rubber with a stacked leather midsole for extra comfort. A small color accent on the instep modernizes the design, boosting style points. Mohinders offers a sophisticated alternative to flip flops.

Lucas offers simpler options: the Terra Mule (a full slide) and the Drift (a half slipper with slight heel coverage).

While the Drift isn’t super secure, it’s more so than the Terra Mule. Both feature stitched construction and crepe soles, providing a thoughtfully made alternative to flip flops, balancing style, comfort, and durability in a more affordable package.

What I liked:

• Quality: Hand-woven leather slides made from natural, undyed water buffalo leather using traditional bag tanning methods.
• Comfort: Easy to slip on, with a footbed lined with soft goat leather and a natural crepe rubber sole.
• Aesthetics: Modern design with a splash of color, elevating the traditional woven leather look.
• Eco-friendly: Uses traditional, environmentally friendly, vegetable tanning processes specific to India.

Downsides, not dealbreakers:

• Limited heel support: No heel coverage, you can’t walk far in these.
• Color limitations: Just tan or brown options available.

Leather Flip Flops: Southern Polished

Flip flops, the kings of summertime casual wear, are probably the most uncomplicated option out there and most folks do not think there’s any point trying to elevate them.

But you can. YouTube cobblers, Trenton and Heath (watch me resole Red Wings with them) created leather flip flops (which they call sandals) under their brand Southern Polished in Tennessee.

These handmade American flip flops use high-quality materials like nubuck leather from Milwaukee, with a midsole of closed-cell rubber and grippy polyurethane outsoles. They provide more support than typical flip flops, with multiple materials and added arch support.

What I liked:

• Quality: Handmade in America by skilled cobblers, using high-quality materials like gray nubuck leather from Milwaukee.
• Comfort: Features a midsole made of closed-cell rubber and extra arch support inside the foot, feeling far more supportive than typical flip flops.
• Durability: Grippy polyurethane outsoles and multiple types of materials used contribute to longevity.
• Aesthetics: Available in a variety of leather options, elevating the basic flip flop design.

Downsides, not dealbreakers:

• Water resistance: You often wear flip flops around water, and leather flip flops feel a little gummy when it’s wet.
• Price: Likely more expensive than standard flip flops, which might deter budget-conscious buyers.
• Limited support: While more supportive than regular flip flops, they still can’t match the ergonomics of closed shoes.

Another option is Hari Mari’s Fields Sandal,. These feature memory foam in the toe strap to reduce friction, an ergonomic footbed with extra arch support, and a contoured heel for stability. The sole is more functional and durable than standard flip flops.

In terms of comfort, both options offer significant improvements over basic flip flops, with better support and cushioning. While not as supportive as closed toe shoes, they provide a noticeable upgrade in comfort compared with normal flip flops. And to be honest, it’s easier to walk in them than in slides.

The leather not only means they’ll last much longer than your rubber Havaianas, they also conform to the shape of your foot with wear.

Can You Wear Boots With Shorts… Ever?

I’m sorry to report that in almost all cases, pulling off boots with shorts is very difficult, if not borderline impossible. Yes, this is a bummer — personally, I have 50 times more boots than any other style of shoes. 

The only boot that I think can look cool with shorts is Red Wing’s Classic Moc Toe Boots. I’ve seen guys wear those boots with shorts and look pretty good, but you have to really be confident and style the rest of the outfit perfectly. There are examples of it working, like Albert of @upstateguystyle in the picture above.

Some guys are comfortable sporting desert boots or chukkas with shorts as well. If you’re trying that out, I suggest sticking to suede.

Wrapping Up

If you’re someone who relishes the opportunity to wear well made shoes, I think you’ve seen some options on this list that made you smile. From chunky, Goodyear welted Moc Oxfords that’ll keep you stable while tromping through the woods to the elevated leather flip flops for beach time shenanigans, don’t leave your feet wanting quality just because it’s hot out!