Unless otherwise stated, all sizes mentioned here are women's sizes.
1. New Balance 327s could be the ideal sneakers for you? Drawing inspiration from New Balance's classic '70s running shoes, they feature a timeless blend of retro and contemporary design that's stylish today and won't look out of place in the future. These versatile sneakers pair perfectly with athleisure, suits, dresses, and beyond — and, most importantly, they're incredibly comfortable.

I own these sneakers in two colors (the black and white shown above and another pair with blue accents that's currently out of stock), and I wear them *constantly*. They're the ideal mix of being slightly chunky without being too heavy, and I adore the vintage-inspired look. And naturally, they're SUPER comfortable. I wear them every day while exploring New York, and I even took a pair with me on a recent trip to Paris, where I walked 81 miles in 8.5 days (I wore the New Balances for 7 out of those 8.5 days!) and felt great every step. I noticed quite a few others wearing them there as well! I’m probably going to buy a third pair (I know, I know...) in the sea salt with sandstone colorway, which is the ideal neutral.
Review highlight: "Absolutely amazing! I need them in every color! If you’re unsure, just get them. I get compliments all the time, and I’m on my feet all day. My favorite New Balances yet!" —Amber B TX
Grab them from New Balance for $99.99 (available in sizes 5–12 and eight color options, plus a version designed for golf).
2. Sam Edelman loafers featuring an elegant double-bit accent; these slip-ons are destined to become your go-to footwear; they're a classic for a reason! And reviewers rave that the leather feels "buttery soft," ensuring comfort right out of the box. Why spend more on Gucci when you can have these?


3. A pair of Aerosoles platform sandals if you're seeking a little extra height but still want ultimate comfort all night long. The platform front helps balance out the three-inch heel, while the ~diamond flex sole~ is crafted to minimize friction. Here's a hint: they might just become your go-to shoes for special occasions.

Review that stands out: "These are incredibly cute and hands down the most comfortable heels I've ever worn. My feet are wide and flat, so high heels usually aren't my friends. For example, I wore them to a baby shower and then walked around Whole Foods without any discomfort. I’ll definitely be picking them up in silver next." —Adriana L.
Find them at Aerosoles or Nordstrom for $135 (available in sizes 5–12, wide, and 14 colors and patterns).
4. Columbia hiking shoes because it's the perfect season for leaf-peeping, and you deserve to enjoy that hike in full comfort. The soles? Made from high-traction rubber, perfect for avoiding those risky falls. The uppers? Waterproof leather and suede, designed to endure countless miles. And those red laces? Just a cute touch to complete the look.


5. A pair of Alohas ankle boots featuring a just-under-3-inch heel to give your look a stylish boost with that '70s-inspired vibe that's all the rage — yet still timeless enough to wear year after year. Heads up: you may find yourself returning for a second pair.

Highly recommended review: "This is my second time purchasing these boots. I got the brown ones a few seasons ago, and they’re still in amazing condition after plenty of wear. I just bought them in black, and they’ve become my new favorite pair! They’re comfortable enough for casual days, and stylish enough to dress up. I wear a size 7.5 in women's US, and ordered a 38. They fit perfectly. I highly recommend these boots to anyone looking for a solid wardrobe staple." —Gabraelle Hanus
Get them from Alohas for $290 (available in sizes 35–44 and four color options).
6. Alternatively, consider a pair of Franco Sarto mid-calf boots that offer great price-per-wear this fall and winter. They pair effortlessly with almost any outfit, adding a subtle stylish touch (thanks to the unique stitching and chunky stacked heel) without overshadowing your carefully chosen look.

7. Rothy's flats crafted from an innovative (and machine-washable!) recycled plastic knit that won’t lose its charm (or hurt your feet). They’re breathable, flexible, and designed to avoid the painful rubbing that some flats with harsh seams cause. Plus, with over 27,000 glowing reviews, they’re definitely worth considering.

Highly recommended review: "These are, without a doubt, the best shoes ever. They're my go-to pair. I’ve been wearing them for 7 years now, and I love them as much now as I did when I first got them." —DEBRA S.
Find them at Rothy's for $149 (available in sizes 5–13 and in 34 colors and patterns).
8. Top-rated Adidas Cloudfoam sneakers that truly live up to their name (no small feat!) — not only do they boast ultra-soft, cushioned soles, but the breathable mesh tops stretch to accommodate your feet. That means no more sweaty feet or painful rubbing, just pure comfort for miles.


9. Cutout mules if you’re not on board with the ballet flat trend but still want a comfy, versatile shoe that complements everything you wear. These shoes are a perfect combination of timeless style, sophistication, and comfort — the ideal trio.

Zou Xou Shoes is a Black woman-owned brand that collaborates with Argentinian artisans to craft handmade footwear since 2015. Their designs are timeless and versatile, perfect for long-term wear. These custom-made mules are available in European sizes, so it's advised to order one size larger. For instance, if your US size is 8, opt for a 39.
Customer testimonial: "These shoes are fantastic! The leather is buttery soft, and they’re incredibly comfortable — no need to break them in." —Eileen Chao
Find them on Zou Xou Shoes on Etsy for $254 (sizes EU 36–42).
10. Thursday Boot Company Chelsea boots feature shock-absorbing insoles, rugged studded leather outsoles, and luxurious glove leather lining, ensuring comfort throughout the day — making these classic boots a staple you'll repeatedly reach for. Customers rave about their durability, with many revisiting their reviews to emphasize how well the boots withstand wear and tear.

11. Doc Martens combat boots — no need to explain why, right? These iconic boots are beloved for a reason and only get better with time. They not only break in beautifully but develop a perfectly worn-in patina on the leather. Featuring air-cushioned soles that are also slip-resistant, these boots are heat-bonded to ensure they last for many years. To maintain their condition, use Dr. Martens Wonder Balsam to nourish and protect the leather as needed!

12. Sorel Kinetic Impact Lace Sneakers are crafted with side vents for added breathability (say goodbye to sweaty feet!) and a special "Livelyfoam" midsole that cushions each step. And let’s talk about those bold, futuristic chunky soles—these sneakers are perfect for anyone who wants to make a statement with their footwear.

13. Birdies velvet flats offer a chic way to try the timeless smoking slipper style without being confined to your ~library~ or ~billiards room~ — if only! These flats feature an impressive seven layers of cushioning in the footbed, paired with a durable rubber sole, allowing you to wear them out on the streets while enjoying the comfort of your favorite cozy slippers.

Customer review: "I’m totally in love with Birdies! As a kindergarten teacher who spends all day on my feet and also as a runner, finding comfortable shoes is a must. These flats are the first ones I can wear all day without my feet aching when I get home. I adore them!" —MARISSA S.
Get them from Birdies for $98 (available in sizes 5–13, wide, and in 21 colors and patterns).
14. Madewell Court sneakers — if you want the perfect pair of plain, low-key sneakers without logos, these are your match. Not to mention, they’re incredibly comfortable with their cushy, supportive "Cloudlift" insoles. No wonder so many reviewers come back for a second pair (or more)!


Customer review: "I’ve been wearing these shoes for a couple of years, and I absolutely love them. They’re incredibly comfortable and go with everything. I’ve walked miles in them, and they still look great and perform well." —CME663
Get them from Madewell for $98 (available in sizes 5–12).
15. Naturalizer slingbacks featuring a petite (but not too flat) 1.25-inch heel and a classic pointed toe for that subtle ~how sophisticated am I~ vibe — all without the risk of twisting your ankle or suffering from cramped toes.


16. Everlane flats crafted from *buttery* soft leather that adapts to your feet over time, making them feel like they were custom-made just for you! Additionally, they feature upgraded insole cushioning, so you can walk in comfort all day while looking chic — it’s like walking on clouds.

Customer review: "This is my third pair of Everlane Day Glove shoes, and I’ll likely buy more. As someone with foot issues, I was hooked after the first pair! I could slip them on and go without any discomfort. The soft leather truly molds to my feet." —TN Mimi
Get them from Everlane for $104+ (originally $138; available in sizes 5–11, and in 11 colors).
17. High-top platform Converse sneakers elevate the iconic Chucks to ~new heights~. And it’s not just for the style (although they certainly look amazing) — reviewers note that the thicker sole also provides extra cushioning for added comfort!


18. Hoka Bondi 8 sneakers come with ultra-cushiony foam that’s surprisingly lightweight — just look at how chunky they are! You’ll feel supported from the moment your heel hits the ground to when your toes lift off. No wonder they’re Hoka’s bestsellers!

Customer review: "I've been dealing with a heel spur and plantar fasciitis pain for around 10 weeks. These shoes have been a GAME CHANGER. Best purchase I've made for my feet." —Ariel
Customer review: "This is my first pair of Hoka shoes, but certainly not my last. They’ve quickly become my favorite sneakers. The toe box gives plenty of room. They’re true to size and incredibly comfortable. Love them." —Gizzys mom
Get them from Hoka for $165 (available in sizes 5–12 and in 21 colors).
Find out why Hoka Sneakers are worth the hype here.
19. Knee-high suede boots come in *eight* different calf widths, allowing you to find a pair that fits perfectly without being too tight or too loose. Whether you wear them over jeans or pair them with dresses and skirts, the memory foam insole and slightly stretchy inner panel ensure comfort all day long.


Customer review: "I absolutely love these boots. They fit perfectly. After two weeks of wear, they've become incredibly comfortable. I have lupus and multiple foot issues, including plantar fasciitis and arthritis, and these boots are so comfortable." —Karen
Get them from DuoBoots for $340 (available in sizes 5–12, eight calf widths, and black leather).
20. Sorel winter boots are highly recommended by reviewers from cold, snowy places like Minnesota — they’re 100% waterproof, feature a tough sole for excellent traction, and will keep you warm. These boots even come with a removable 9mm thick felt liner with a fleece cuff that you can wash. Let! It! Snow!


21. Lucky Brand ankle boots come in a variety of colors and materials, a testament to their popularity over the years. These boots sit low enough to show off your stylish ankle (perfect for those fun socks) or rest just beneath pants without creating any bunching at the calf.


22. Vintage-inspired Reebok sneakers featuring foam-padded sock liners and shock-absorbing midsoles for added comfort, offering a timeless retro look that pairs effortlessly with nearly anything in your wardrobe.


23. Suede boots that at first glance appear to be classic black ankle booties with a chic, slightly pointed toe. But take a closer look, and you'll spot the stylish dark green embossed croc heels — if you're looking to get compliments on your footwear, these are the ones to choose.

Ma’am Shoes is a woman-owned small business known for creating stylish, comfortable shoes that are built to last for years. If you're between sizes, the brand suggests sizing up.
Promising review: "Breaking in new shoes can be tough, especially when you're on your feet all day. But I'm happy to say that these were an exception — they felt like they were already broken in after the first day of wear! They were that comfortable! I sized half a size up and I’m so glad I did. I’ll definitely be buying more soon." —Ashley Cornett
Purchase them from Ma'am Shoes for $300 (originally $350; available in sizes 5–11).
The reviews in this post have been condensed for brevity and clarity.