Most Comfortable Ballet Flats & Mary Janes to Wear This Fall 2025
I tend to wear either super comfy slippers or high heels, lol. But sometimes, you need an elevated shoe, but stilettos just won’t do. (Ask my sister. I watched her navigate through the yard in 3-inch heels recently, and it was a scary sight!) Today, I’m sharing shoes that give our feet a break without giving up style. That’s where ballet flats and Mary Janes shine. These time-honored classics are making a comeback with fresh details, such as square toes, adjustable straps, and cushy insoles, which mean no more blisters after just ten minutes of wear. Yes, please!
Comfortable Ballet Flats & Mary Janes For Fall
Italian Leather Pointed Bow Flats
These Italian Leather Pointed Bow Flats are super cute! I’ve worn them non-stop since I bought them. I wore them to my mother’s, and we were leaving to run some errands. As I walked down her concrete steps, I remembered that I had forgotten something in the house. I turned around too quickly and stubbed my toe on the concrete. It scuffed the leather, and it almost made me sick.
I ordered another pair because I loved them so much, and I also purchased them in almond.
Mary Jane Flats
Square-toed shoes have a unique, modern look with their sharp, squared-off toe, which sets them apart from the usual rounded or pointed styles. Wearing red shoes might be out of your comfort zone, but don’t fret, these are also available in twenty other colors! This is a great way to incorporate the Mary Jane shoe trend into your wardrobe and keep it looking modern and fresh.
Talbots Vera Leather Mary Jane Ballet Flats – Metallic Crackle
Well, hello sparkle! These metallic Mary Jane Flats are like jewelry for your feet. The crackled leather upper adds just enough shine to dress up jeans or a simple black dress. Plus, that classic Mary Jane strap keeps them secure, so you can wear them from brunch to a date night without worrying about slipping.
- Metallic leather adds a little glam
- Secure strap for extra support
- Cushioned insole for all-day wear
- Fun statement shoes for fall outfits
Talbots Blaine Soft-Sole Loopy Woven Ballet Flats
If you love texture, these Woven Ballet Flats are for you. They have that classic ballerina vibe but with a modern twist. The soft sole and cushioned insole make them so easy to wear, even if you’re on your feet a lot. These will be a staple with trousers, skirts, or your favorite jeans.
- Woven leather adds interest
- Flexible sole that moves with your foot
- Cushioned insole for optimum comfort
- Perfect everyday shoe
Quince Italian Leather Mary Jane Ballet Flat – Cognac
This Mary Jane Ballet Flat is so chic. The adjustable strap makes them feel secure, and the warm cognac shade is just right for fall. These Mary Janes have a little nostalgia, but the sleek design makes them completely modern.
- Adjustable strap for secure fit
- Luxe Italian leather upper
- Cushioned footbed for comfort
- Versatile fall color pairs with neutrals and denim
Quince Italian Leather On-the-Go Ballet Flats
These Ballet Flats are the ones you keep by the door. The zero break-in time is a lifesaver, and the simple square toe design makes them modern and polished. If you need an everyday go-to, this is the best pair for you.
- No break-in time, wear them right away
- Square toe adds a stylish edge
- Cushioned insole for comfort and arch support
- Goes with literally everything
Quince Italian Leather Mary Jane Flat – Merlot
Oh, this color! The merlot shade feels rich and luxe for fall. The Mary Jane strap and jewel-encrusted mesh make these flats feminine without being overly fussy. These are a pair you’ll want to wear all day long.
- Gorgeous fall-ready merlot shade
- Classic Mary Jane strap
- Jewel-Encrusted Mesh
- Works for casual or dressy outfits
Quince Italian Leather Handwoven Ballet Flat
These Handwoven Ballet Flats feel elevated and special, like something straight off the runways. The flexible leather molds to your foot’s shape, while the cushioned insole keeps you comfy. These are a chic swap for heels when you still want polish.
- Handwoven leather detail
- Flexible fit adapts to your foot
- Cushioned insole reduces blisters
- Chic alternative to heels
Franco Sarto Marylee Round Toe Mary Jane Flats
I’m a big Franco Sarto fan! If you need a little extra room, these Mary Janes have a round toe and a wide toe box that’s friendly for bunions or extra-wide feet. The strap keeps them snug without squeezing, and they’ve got enough cushion for hours of wear.
- Round toe design with roomy fit
- Strap adds security and style
- Cushioned insole for support
- Classic Mary Jane silhouette
Franco Sarto Oakes Square Toe Ballerina Flats
These Ballerina Flats bring a little runway style to real life. The square toe feels modern, while the cushioned insole makes them practical. Also available in black and maroon.
- On-trend square toe design
- Cushioned insole with extra support
- Polished look for work or dinner
- Versatile neutral color
Style & Co Baileyy Woven Snip Toe Ballet Flats
It’s a reverse mullet, lol. Business in the back and party in the front! All jokes aside, these Ballet Flats are playful and lightweight, with a woven design that gives them a dainty shoe feel. Perfect for casual days when you still want something cuter than sneakers.
- Woven upper adds texture
- Snip toe silhouette is feminine and fun
- Cushioned insole prevents blisters
- Lightweight for all-day wear
FAQs About Ballet Flats & Mary Janes
Are ballet flats comfortable for all-day wear?
They can be! Comfort depends on the brand, the cushioning, and the support built into the shoe. Look for styles with padded insoles, flexible soles, and a little arch support. I’ve found that the newer versions of ballet flats are much kinder to our feet than the old-school, paper-thin ones we may remember.
Can women over 50 still wear ballet flats and Mary Janes?
Absolutely! Ballet flats and Mary Janes are timeless, and they work beautifully for any age. The key is choosing updated styles that look modern, think sleek shapes, pointed or almond toes, or elevated details like buckles and textured fabrics.
What’s the difference between ballet flats and Mary Janes?
Ballet flats are simple, slip-on shoes with a low profile, while Mary Janes have that signature strap across the top of the foot. Both are feminine and versatile, but Mary Janes often feel a little more polished because of the strap detail.
How can I style ballet flats and Mary Janes for fall?
Pair them with ankle pants, jeans, or even midi skirts. For fall, I love them with darker washes of denim, tailored trousers, or cozy knits. A structured jacket or cardigan helps balance out the softness of the shoe.
Do ballet flats need to be broken in?
Some do, but it depends on the material. Leather usually softens with wear, while fabric or knit styles tend to feel comfortable right out of the box. If you’re worried about rubbing, a little moleskin or cushioned insert can help during the break-in stage.
Can I wear ballet flats and Mary Janes with dresses?
Yes! They look darling with dresses of all lengths, especially midi and knee-length styles. If you’re not a fan of heels, they’re the perfect way to look polished without sacrificing comfort.
No matter if you like metallics or simple leather, the right pair of shoes can take your fall outfit from basic to polished in a heartbeat. The best part? These styles focus on comfort, with cushioned insoles, arch support, and soft materials so you can actually wear them without a second thought. Please let me know in the comments which pair you like best!
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😊Can’t get over the great prices on Quince flats. I will be trying them!!!
😊I like how flats can give a more polished look rather than sneakers.
🙂 Pretty ballet flats. I have feet problems. I can’t wear them.
😊 I’ve always put my flats in the “spring” category. I like these and the darker tones are real nice for fall.
Do you like Tieks? I wear them all the time and they hold up so well. Last for years. They are pricey but you definitely get your moneys worth.
I’ve not tired them.
Found it 🙂 All the flats are super cute.
😀my 72-yr-old feet love flats!
😊 Cute shoes! I really like the green Franco Sarto flats.
Ohhh, those Talbot’s green flats and Style & Co brown flats are calling my name! 😁
🙂 Love the gold Talbot’s Mary Janes.