Comfortable Shoes Don't Have To Be Boring — These 30 Stylish Pairs Are Proof

From cloud sandals to chunky sneakers, stay cool with these shoes.

Written by Allison Bolt
Originally Published: 
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This list proves one thing: there is no reason to choose between style and comfort when it comes to your footwear. You can have comfortable, supported feet all while looking so cute and stylish — just consider the chunky sneaker that plays into the ‘90s trend happening right now.

There are pull-on styles and even a pair with ventilated insoles — and they’re all so cute. This list also has plenty of on-trend sandals with a thick platform, slide design, or large buckle straps. There’s even a cloud sandal with all three features. Whether you want sneakers, flats, sandals, or loafers, you’ll look and feel so good while rocking these shoes.


A Pair Of Hiking Sandals With Trendy Braided Straps

These durable hiking sandals have enough arch support and waterproof capabilities to make them great for outdoor treks. But, they’re still stylish enough for all of your non-hiking outfits. They have adjustable braided straps with that little toe-ring design that’s so trendy — but comfy. Even with these intricate and trendy straps, you simply pull on these lightweight sandals.

  • Available sizes: 5.5-6 — 10.5-11
  • Available colors: 5


These Chunky, Edgy Leather Oxfords With A Non-Slip Platform

These lace-up oxfords are complete with a thick rubber platform that’s actually comfy and lightweight, in addition to being totally non-slip. These high-contrast and trendy platforms have an edgy style to them, thanks to the durable leather design and classic oxford accents on top.

  • Available sizes: 5 — 10
  • Available colors: 11


A Pair Of Leather Loafers With Padded Insoles For Walking

These 100% leather loafers are actually called walking loafers. Stroll around town all day in comfort thanks to flexible and comfortable details, like the padded insoles and durable rubber circles on the soles that easily bend and massage your feet. These loafers can simply be slipped on, which makes them an easy option for everyday wear.

  • Available sizes: 5 — 12
  • Available styles: 44


These Low-Top Sneakers With Super Chic Textured Fabric

These low-top sneakers are finished off with a canvas fabric with a unique texture that makes them feel so chic. Of course, they still have that classic rubber sole and rounded-toe design that’s easy to wear, and the timeless metal grommets on the side keep them nice and breezy.

  • Available sizes: 5 — 11
  • Available styles: 24


These Lightweight Flats That Are Made From A Breathable Mesh

Not only do these pointed-toe flats have a breathable insole made from a soft, cushioned memory foam, but they also have a bunch of ventilation. The stretchy, sweat-absorbent mesh fabric on top lets plenty of air in to keep your feet feeling fresh. Best of all, these shoes are bendable enough so you fold these memory foam flats completely in half.

  • Available sizes: 5 — 11
  • Available styles: 19


These Wide-Strap Sandals That Feel So Lightweight

These wide-strap sandals are so durable, and are complete with a waterproof, single color or pattern finish that honestly looks so chic — even though they’re slides. Beyond being minimalist and so cute, they also have the comfy EVA rubber sole that is extra-lightweight sole and molds to your foot.

  • Available sizes: 6 — 11
  • Available styles: 42


These Cork Sandals With Funky Criss-Cross Straps

These chunky sandals are complete with that classic, flexible cork footbed that’s so comfy and always in style. These cute sandals even have soft soles, thanks to the 100% suede lining. Plus, these sandals are complete with funky straps made of a faux-leather material that makes these criss-cross straps super durable.

  • Available sizes: 5 — 13
  • Available styles: 21


These Memory Foam Sneakers With A Breathable Construction

The knit fabric isn’t the only breathable yet plush detail on these lightweight, bungee lace sneakers. They also have a ventilated insole that’s made of soft memory foam to reduce the pressure on your feet. These slip-on sneakers are even complete with an easy-to-adjust heel, so you can push down the back and wear them as slides to let your heels breathe.

  • Available sizes: 5.5 — 10
  • Available colors: 9


These Washable Loafers That Are Made From Breathable Cotton

Just because these breathable shoes have a classic loafer design doesn’t mean they’re uncomfortable. Actually, the upper sole is made of 100% cotton canvas that’s so flexible. This breathable canvas is finished off with elastic laces on top that are cute but make these easy to slip on. Plus, you can remove the memory foam insole if it doesn’t work with your socks — but you may want to keep it around because of the cushiony platform that reduces sweating and odors.

  • Available sizes: 4 — 12
  • Available styles: 15


A Pair Of Cushiony Cloud Slides That You’ll Want To Wear All Day

Yes — you can totally reach for foam slide-on sandals in the morning and still look chic, whether you’re WFH or heading out the door. The thick cushioning has a simple, textured design that molds to your foot and still looks minimalist with all of your outfits. This sleek design even has a small platform that’s 1.75 inches and super flexible.

  • Available sizes: 5 — 12
  • Available styles: 21


These Unique Running Sneakers That Feel Super Secure

It’s all about the unique straps with these pull-on running sneakers. They stretch across the lightweight fabric to replace the laces, which adds a snug, sock-like fit that feels super secure on your runs. Plus, they have a lightweight cloud foam sole that adds cushioning for every single step.

  • Available sizes: 5 — 12
  • Available styles
  • : 33


These Ballet Flats With A Chic Knit Texture

These ballet flats are made with a knit fabric to make them extra-stretchy and chic up top. Of course, it’s also more breathable than those patent leather flats that we’re all used to. Beyond the functional yet cute tip, these shoes have cushiony memory foam insoles made with air cooling technology.

  • Available sizes: 5 — 11
  • Available styles: 8


A Pair Of Slip-On Mules With A Woven Finish

These slip-on mules have a chic woven texture that stands out from all of your plain, smooth shoes. They’re complete with a super comfortable heel that’s not even an inch tall, giving you the chic look without any of the pain. These flexible mules also have a classic pointed toe and padded insoles with a curved design that’s not constricting around your foot.

  • Available sizes: 6 — 11
  • Available colors: 35


These Vegan Mules With A Golden Touch

These are the pointed-toe mules to grab to elevate your look. Each faux leather shoe a shiny chain that works well with slacks, jeans, skirts, and dresses alike. Beyond being so chic with a teeny heel, these mules are a practical option thanks to the comfy and soft padded insole and loafer-like stitching.

  • Available sizes: 6 — 10
  • Available colors: 13


This Pair Of Unique Leather Loafers That Feel So Soft

These leather loafers are super unique with their polka dot rubber soles. It’s a super flexible design that provide plenty of traction. The soft leather on top will bend with you as you walk and is complete with a chic, gold-tone accent. You can also adjust the breathable leather to wear these lightweight loafers like slides.

  • Available size: 4.5 — 12
  • Available colors: 8


These Mesh Sneakers That You Can Pull On Quickly

These lightweight sneakers with memory foam insoles will absorb the shock on your jogs. They are so easy to pull on, thanks to the breathable mesh fabric on top that’s so stretchy, you’ll barely need to use the pull tabs on the front and back. This fabric also has a rib-knit finish that makes them look even trendier than your usual go-to sneakers.

  • Available sizes: 5 — 13
  • Available colors: 19


These Grippy Slip-On Sneakers With Over 10,000 Ventilation Holes

These slip-resistant sneakers look like a classic sneaker — but the one-piece knit upper has over 10,000 holes that make these extra breathable. These sneakers are also complete with a striped texture on the lightweight soles that don’t just look cool but also help with shock absorption and grip.

  • Available sizes: 6 — 10
  • Available colors: 11


A Pair Of Low Top Canvas Sneakers That’ll Never Go Out Of Style

These low-top sneakers are a classic for a reason. These round-toe shoes are made from a breathable yet cute canvas fabric, and the two ventilation holes on the side add to the airflow. These non-slip sneakers also have stitching on the side that adds a chic, contrasting detail.

  • Available sizes: 5 — 11
  • Available styles: 22


These Pull-On Shoes That Are So Plush

These unique pull-on shoes are perfect for taking your pup out in the morning. They’re complete with quilted fabric on top that’s so plush but also happens to be windproof. Plus, the soft terry lining makes them feel just as warm and cozy as slippers. Meanwhile, the waterproof sole and sneaker shape (that you can fold over to wear as slides) make these shoes look super put together.

  • Available sizes: 6 — 15
  • Available colors: 18


A Pair Of On-Trend Mary Janes With Comfy Insoles

This pair of Mary Jane shoes are complete with that leather finish and single strap that’s an iconic look. These adjustable, buckle-closure flats are also secretly comfy, because the insoles have a bunch of plush padding that actually reduces pressure on your feet. These shoes are practical from top to bottom, thanks to the slip-resistant rubber soles.

  • Available sizes: 5 — 11
  • Available colors: 8


These Booties That Keep Your Feet Cool

These booties are made with faux-leather, but they’ll keep your feet cool with the sandal-like design that’s open at the front and the heel. There are also handy ventilation holes on top that add a trendy polka dot texture. Meanwhile, the block heel and zipper still make them look and feel like a classic bootie, while making them easier to put on than other boots.

  • Available sizes: 5.5 — 11
  • Available colors: 6


This Pair Of Structured Combat Boots That Are Secretly So Soft

You can totally get the structured combat boot look with these rubber-sole boots. Only you’ll know that the faux-leather on these edgy boots is super soft. These shoes may look hard, but there are memory foam padded insoles tucked inside, and you’ll still get a chunky sole to finish off the look.

  • Available sizes: 5 — 13
  • Available colors: 4


These Mesh Sneakers With The Most Unique Tread

The zig-zag tread on these sneakers is unique, but it also looks minimalist enough to go with patterned leggings or any other bottom of your choice. The simple white sole is lined with a strip of grippy rubber that adds a non-slip yet stylish element. The low-profile top with mesh fabric balances out the bold bottom, and inside is a cushiony memory foam insole.

  • Available sizes: 6 — 11
  • Available colors: 2


These Cloud Slides With Extra-Trendy Buckles

These cloud slides pack on another trendy detail with those buckle accents. So, you get that 1.75-inch foam sole that’s waterproof and molds to your foot and oversized adjustable buckles, combining two trendy shoes into one. These soft rubber shoes are easy go-tos for around the house or around town.

  • Available sizes: 5 — 12
  • Available colors: 17


These Cork-Sole Sandals That Are Super Durable

These platform sandals are complete with a contrasting white tread on the bottom that’s super cute and helpful. It makes the chic cork sole a little more durable because it’s lightweight yet wear-resistant, plus it looks trendy. On top, these cushioned sandals have a leather insole and thick elastic straps that feel so secure.

  • Available sizes: 5 — 11
  • Available colors: 19


These Sneakers With A Comfy Add-On In The Sole

The non-slip soles of these sneakers are chunky for a reason (other than the trendy factor). There’s actually a shock-proof air cushion built right into the sole. It also has a lightweight mesh top that’s free of uncomfortable metal hardware or laces. Plus, the wide design at the front gives your toes and socks plenty of room.

  • Available sizes: 5.5 — 10.5
  • Available colors: 14


These Chunky-Sole Sneakers With Trendy Tread Accents

The non-slip tread is possibly the best part of these low-top canvas sneakers, which adds a unique accent to the trendy and chunky 2-inch sole. Plus, it makes the bottom of these canvas sneakers super padded and flexible. Beyond the bottom of these edgy low tops, you have a memory foam insole that one reviewer described as “so squishy.”

  • Available sizes: 6 — 11
  • Available colors: 5


These Open Toe Sandals That Have That Trendy Crocs Comfort & Style

If you feel like you’re seeing Crocs everywhere, you’re not imagining things. These sandals take the brand’s iconic comfort grip and waterproof EVA material and turns them into sandals. Available in dozens of colors and styles, these open toe sandals have soft, flexible straps that make them easy to slip right on.

  • Available sizes: 4 — 17
  • Available styles: 52


These Fuzzy House Shoes With Plenty Of Arch Support

These plush house shoes are made with a rubber sole that has a foam-like texture that’s surprisingly comfortable and full of arch support. These slippers have a trendy, faux rabbit fur strap that looks and feels so plush, but the bottoms are still sturdy and anti-skid.

  • Available sizes: 5 — 11
  • Available colors: 29


These Faux Leather Flats With Functional Floral Cutouts

These faux leather ballet flats are still super breathable, because the stylish floral eyelets double as ventilation holes. Beyond keeping your feet cool, these shoes have a soft memory sole insole and an extremely flexible build, which means they have with you as you walk all around time.

  • Available sizes: 5 — 11
  • Available colors: 13

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