As mid-August rolls around, now is the perfect time to start considering adding versatile pieces in your wardrobe that can ease the transition from summer to fall. After all, I’m a New York City-based travel writer, and I know too well that this is one of the trickiest times for footwear, especially on the East Coast, where it’s starting to be too cool for sandals but not quite chilly enough for boots. The ideal shoes for this in-between season — and really, for any season — are comfortable flats. 

Whether you’re into Mary Janes, ballet flats, or loafers, the styling possibilities are endless. Pair them with a breezy floral maxi dress while it’s still warm, or switch to jeans and a cozy sweater when the crisp air starts to set in. Come spring, they’ll look just as chic with a button-down and pleated skirt. Truly, the options are limitless. To speed up your search for the perfect flats (and spare you from the blisters that come with an unsupportive pair), I’ve rounded up nine of the most comfortable yet stylish flats to help you glide through the summer-to-fall transition with ease.

Rekayla Mary Jane Flats

Affordable, comfortable, and stylish, the Rekayla Mary Jane Flats are sure to be your most-worn shoes in the coming weeks. They can instantly elevate a simple jeans-and-tee combo and are perfect for fall when you want to look more polished than with sneakers. One Amazon reviewer detailed how comfortable they are, saying, “I walk 3 miles every day in these, and they never hurt my feet. [They’re] perfect for everyday use.” With premium rubber soles that are slip-resistant, these flats keep the walk to work comfy so there’s no need to pack extra Band-Aids.

Amazon Essentials Women’s Pointed-toe Ballet Flats

What I love most about ballet flats is their effortless simplicity. The Amazon Essentials Pointed-toe Ballet Flats exude an old-money, classic vibe, striking the perfect balance between feminine and fashionable. With over 6,500 five-star ratings, reviewers can’t stop praising their comfort as well. As one happy customer put it: “These are so comfortable — they actually have a lot of padding inside and don’t kill my feet after wearing them all day at work.”

Dream Pairs Women’s Backless Loafers

The Dream Pairs Backless Loafers give you the sophistication of a traditional loafer without the discomfort of your ankle rubbing against the back. The gold hardware adds a luxe touch, especially when paired with a matching metallic belt. What’s more, these loafers are also an affordable gateway to the chic wearable workwear trend, coming in at under $25 with their current discount. 

Nordstrom Mary Jane Flats

If you’re considering investing in the Nordstrom Mary Jane Flats, you won’t be disappointed. Style them with straight-leg jeans, a striped Breton top, and a black blazer for that classic Parisian chic vibe — or go all-out preppy with a pleated mini skirt and sweater vest. They’d also pair beautifully with a fit-and-flare dress if you’re feeling fancy. While classic black is always a safe and versatile bet, the red option is also calling my name — especially with how striking all-black outfits look with a pop of red accessories.

Linea Paolo Marley Mary Jane Flats

These flats have a charming retro flair with their circular strap design and squared-off toe. The cream color is a personal favorite as it’s perfect for styling in summer, fall, and spring. Not only do they look fabulous, but reviewers also rave about their comfort. One Nordstrom customer gushed, “These shoes exceeded my expectations. The leather is buttery soft, and they’re among the most comfortable shoes I own.” They added, “I usually have to ‘break in’ new shoes because of my wider feet, but not these! They were comfortable right out of the box thanks to the soft leather.”

Madewell Vernon Bit Leather Loafers

These loafers are timeless staples that never go out of style, easily transitioning your wardrobe through the seasons. Whether you’re pairing them with trousers and a button-down for a polished office look or with jeans and a sweater to elevate a casual outfit, they’ll complement nearly anything in your wardrobe. The shiny hardware adds a luxe touch, while the brand’s MWL Cloudlift Lite padding ensures you can wear them comfortably from morning to night.

Madewell Greta Ballet Flat Mules

The deep merlot shade of the Greta ballet flats is simply stunning; it’s a color that stays on-trend year-round, especially in fall and winter when rich reds are in high demand. This shade pairs beautifully with neutrals like blue jeans and a white blouse, or it can be the perfect pop of color against an all-black outfit. There are also other shades available, including suede options that are even more ideal for the chillier months.

Linea Paolo Celina Pointed-toe Slingback Flats

Classic black or fiery red — whichever you choose, you’ll want to decide quickly because these shoes are already flying off the shelves. If you’re heading to the office, a cocktail party, or happy hour, these versatile flats will effortlessly fit into every aspect of your life with their on-trend elegance. And it’s not just us who are obsessed; a Nordstrom customer raved, “They have a French chic vibe and are comfy enough to wear all day. I have the red pair and love them — [I’m] going back for the black next.”

J. Crew Zoe Ballet Flats 

The inner ballerina in me can’t get enough of these flats; they bring back all the nostalgia. The delicate bow paired with the flexible, comfortable sole creates the perfect ballet flat, adding a touch of girlish charm to any outfit. They’re simple, chic, and effortlessly stylish. Even better, they’re on sale, so grab a pair before they’re gone!

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