9 Comfortable Flats to Transition Your Travel Wardrobe from Summer to Fall — Starting at $24

As mid-August approaches, it’s the ideal moment to start incorporating versatile pieces into your wardrobe that facilitate the shift from summer to fall. As a travel writer based in New York City, I know all too well that this is a tricky time for footwear—especially on the East Coast, where it’s becoming too cool for sandals but not quite chilly enough for boots. The perfect shoes for this transitional season—and honestly, any season—are comfortable flats.

Whether you prefer Mary Janes, ballet flats, or loafers, the styling options are endless. Wear them with a light floral maxi dress while the weather is still warm, or switch to jeans and a cozy sweater as the crisp air sets in. Come spring, they’ll look just as stylish paired with a button-down and pleated skirt. The possibilities are truly limitless. To make your search for the perfect flats easier (and to avoid the blisters from unsupportive shoes), I’ve compiled a list of nine of the most comfortable yet fashionable flats to help you navigate the summer-to-fall transition smoothly.

Rekayla Mary Jane Flats

Affordable, comfortable, and stylish, the Rekayla Mary Jane Flats are bound to become your go-to shoes in the upcoming weeks. They can effortlessly elevate a simple jeans-and-tee outfit and are ideal for fall when you want a more polished look than sneakers provide. One Amazon reviewer shared their experience, stating, “I walk 3 miles every day in these, and they never hurt my feet. [They’re] perfect for daily wear.” With high-quality rubber soles that offer slip resistance, these flats ensure a comfortable commute to work without the need for extra Band-Aids.

Amazon Essentials Women's Pointed-Toe Ballet Flats

What I appreciate most about ballet flats is their effortless elegance. The Amazon Essentials Pointed-Toe Ballet Flats embody a classic, timeless aesthetic, perfectly balancing femininity with style. With over 6,500 five-star reviews, customers rave about their comfort as well. As one satisfied buyer remarked: “These are incredibly comfortable — they have substantial padding inside and don’t hurt my feet even after wearing them all day at work.”

Dream Pairs Women's Backless Loafers

The Dream Pairs Backless Loafers offer the elegance of a classic loafer without the irritation of your ankle rubbing against the back. The gold hardware provides a touch of luxury, especially when paired with a coordinating metallic belt. Additionally, these loafers are a budget-friendly entry into the chic workwear trend, currently priced under $25 with their available discount.

Nordstrom Mary Jane Flats

If you’re thinking about adding the Nordstrom Mary Jane Flats to your collection, you won’t regret it. Pair them with straight-leg jeans, a striped Breton top, and a chic black blazer for a classic Parisian look — or embrace a preppy style with a pleated mini skirt and sweater vest. They also look stunning with a fit-and-flare dress for more formal occasions. While classic black is a versatile choice, the vibrant red option is also tempting — especially how striking it contrasts with all-black outfits for a stylish pop.

Linea Paolo Marley Mary Jane Flats

These flats boast a delightful retro charm with their circular strap and squared toe design. The cream hue is a personal favorite, making them ideal for styling across summer, fall, and spring. Not only are they visually appealing, but customers also rave about their comfort. One Nordstrom reviewer exclaimed, “These shoes surpassed my expectations. The leather is luxuriously soft, and they’re among the most comfortable pairs I own.” They continued, “I typically need to ‘break in’ new shoes due to my wider feet, but not with these! They felt great right out of the box thanks to the supple leather.”

Madewell Vernon Bit Leather Loafers

These loafers are classic essentials that seamlessly adapt to any season. Whether styled with tailored trousers and a button-down for a sleek office look or paired with jeans and a cozy sweater for a more casual vibe, they enhance almost any outfit. The gleaming hardware provides a touch of luxury, while the brand’s MWL Cloudlift Lite padding ensures all-day comfort from morning to night.

Madewell Greta Ballet Flat Mules

The rich merlot hue of the Greta ballet flats is absolutely eye-catching; it’s a color that remains stylish throughout the year, particularly in fall and winter when deep reds are especially popular. This tone pairs wonderfully with neutrals like blue jeans and a white top, or it can serve as a vibrant accent against an all-black ensemble. Additionally, other shades are offered, including suede options that are perfect for the colder seasons.

Linea Paolo Celina Pointed-toe Slingback Flats

Whether you opt for classic black or bold red, act fast — these shoes are flying off the shelves! Perfect for the office, cocktail parties, or happy hours, these chic flats seamlessly blend into every facet of your life. It’s not just us singing their praises; a Nordstrom customer enthused, “They exude a French chic vibe and are comfortable enough for all-day wear. I have the red pair and adore them — [I'm] heading back for the black next.”

J. Crew Zoe Ballet Flats 

These flats awaken the ballerina within me, evoking sweet nostalgia. With their charming bow and flexible, comfy sole, they embody the perfect ballet flat, effortlessly adding a girlish touch to any ensemble. Simple, chic, and stylish, these beauties are on sale — so snag a pair before they’re all gone!

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