Naturalizer Crista Mary Jane Flat

Fawn prints and leopard spots are in a bit of a competition as we speak, but Naturalizer settles the score — once and for all. This Crista flat flaunts a chic square toe, not one but two buckle-clad Mary Jane straps, and the brand’s proprietary Contour+ Comfort tech for plush landings sans impact. I liked donning the shoe with dark-wash straight-leg jeans, billowing maxi skirts, and even capri pants during my rounds of testing. If you have a wider foot, like I do, you might want to think about adjusting said straps to accommodate its proportions or simply buying the style in Wide. Otherwise, the Crista fits like a second skin and goes a long way in beautifying even the most casual of ensembles. (Leopard print? Why, it’s a neutral!)

All in all: When you wish to look good without sacrificing arch support and allover cushioning, turn to the Naturalizer Crista Mary Jane Flat. It aces one of fall’s hottest designs while prioritizing what’s most important — your comfort.

Rothy’s The Almond Slingback Flat

While the eyelet-equipped iteration of this flat that I tried out is no longer available online, the pictured cap-toe darling is an in-stock close second — specializing in effortless preppiness and around-the-clock wearability. The label is known for using recycled water bottles to produce its top-rated footwear, and The Almond Slingback is no exception. It’s sustainable, it’s flexible, it’s put-together, and its slingback closure is a fit for the warmer weeks of early fall (or those 70-degree days your town experiences in the middle of November, you lucky duck).

All in all: Ideal for work meetings and brunches with the gals alike, this slingback flat is a match made in heaven for sartorial sensibilities that lean more classic rather than experimentative. Nothing, after all, could be more timeless than a cap-toe shoe. Just ask Chanel.

Aerosoles Amina Dress Flat

Grab Aerosoles’ Amina while it’s on a final sale and proceed to relish the flat’s chunky hardware, statement ruching, Ortholite foam insole, and grippy outsole for traction on all surfaces. Swathed in glossy faux leather, the shoe will complement everything from a sharp-shouldered blazer to those long-sleeve LBDs you gravitate towards each autumn.

Because the Amina’s prominent chain cannot be expanded or taken off, I found that it dug into the top of my foot ever so slightly. That being said, consider sizing up or cosigning the product’s Wide variation, similar to the above Naturalizer bestseller.

All in all: Edginess meets sophistication in this dressy flat for women that swaps stiffness for softness while staying versatile in context of your wardrobe at large. That under-$60 price, by the way, makes it all the more alluring.

Sarah Flint Stella Flat

Luxury, direct-to-consumer footwear and accessories brand Sarah Flint merges top-tier quality with mid-tier price points (and it has managed to win a seal of approval from the likes of Meghan Markle and Amal Clooney). I was fortunate enough to test Sarah Flint’s Stella model, and it immediately won me over with thoughtful details like a V-shaped vamp and a high-end, 100-percent calf leather composition.

Handcrafted in Italy, this shoe is the dictionary definition of an investment that keeps on giving: across seasons, across years, and certainly across weekly outfits. I, for one, wore the Stella to work, date nights, solo evenings spent on Broadway, and every activity in between (save for actual exercise). It never once dug into my skin, left blisters in its wake, or led to dreaded chafing. What more could a woman want?

All in all: Comfy but not at the cost of elegant looks, the Sarah Flint Stella Flat is a slingback that breaks the rules — demanding to be worn year-round. Its black patent leather exterior will appeal to the fashion set, while a shape that aligns with the contours of a woman’s foot will bless the flat’s every last wearer, regardless of personal aesthetic.

Skechers Cleo Square Flat

My lavender hue of choice for the Skechers Cleo flat is long gone from online shelves, but you can still get it in Navy, Black, or the trend-aware Mocha directly at Amazon (yes, that means free delivery for good measure).

Skechers’ famous, air-cooled memory foam takes center stage here, joined by a stretchy upper with the sensation of a sock and a wider-than-average toe box that felt consistently amazing during my longer walks. I also appreciated the shoe’s woven texture plus machine-washable makeup and envision continuing to enjoy these elements in the months to come, alongside all manner of styling equations.

All in all: I didn’t think this was the most stylish flat I tested for the article, but it was no doubt the most practical and ergonomically minded. Shop now if your feet need a break (and you don’t want to break your wallet while securing it for them).

Dr. Scholl’s Wren Mary Jane Flat

You might be familiar with Dr. Scholl’s vis-à-vis its industry-leading orthotics, but the circa-1906 brand makes shoes, too — and they’re a far cry from what now occupies your grandma’s closet. Case in point is this Wren Mary Jane: leveled up with anti-odor technology, partially plant-based foam, geometric mesh cutouts, and a solitary strap at center.

Customers regularly shout out the style’s inconsequential weight, cushioned feel, and all-day breathability, which I agree with word for word after getting properly introduced to the Wren. Pair with a suede bag and a cardi tied over the shoulders of a white dress for best results.

All in all: This modern flat is light as air, low-profile, and environmentally conscious. It’s perfect for shoppers who desire all the perks of a luxury shoe without the inaccessible price tag.

M.Gemi The Loriana Flat

Another premium, direct-to-consumer destination for shoes and handbags, M.Gemi distinguishes itself from competitors by partnering with family-owned artisanal workshops in Italy. You better believe, then, that each of its shoe releases harnesses centuries-old techniques while being guided by present-day design codes and consumer demands.

I’ve owned The Loriana for over a year now, requesting to sample it for a previous piece. She’s been with me from 10,000-step days to indulgent evenings and nine-to-five corporate obligations… and it’s safe to say this leading women’s flat didn’t falter or fail to meet my high expectations throughout it all. The Mary Jane has an exaggerated, pointy profile, barely there ruching, and flexible back that allows it to moonlight as a mule. Either way, you won’t need to carry Band-Aids around, as The Loriana’s delicate Nappa leather (made in Leather Working Group–certified tanneries) will feel less like a punishment and more like a red-hot kiss.

All in all: You won’t regret spending over $300 on this beloved M.Gemi buy, since it makes every penny count courtesy of impeccable attention to detail and the kind of appearance you’ll be dying to show off on city streets.

Larroudé Pavlova Ballet Flat

There are flats, and then there are Larroudé flats. The made-in-Brazil, It-girl-approved label was launched by a longtime fashion executive, so of course it’s a pro at ideating silhouettes and finishes that stick the landing. Larroudé’s Pavlova is testament to its keen knowledge of high-fashion aesthetics — being steeped in raffia, trimmed in grosgrain, and dotted with a bow on top. The brand positions this shoe as a savior for “warm-weather styling,” but you just might get away with sneaking it into the fall season.

A rounded toe, memory foam insides, and a touch of gleaming, branded hardware seal the deal on this being a not-to-miss purchase that’s selling out of sizes all too quick for comfort. (PSA: It’s also on offer in snakeskin, burgundy leather, and cherry-colored satin options, encouraging you to shop the flat in multiples).

All in all: Artful yet purposeful in its intention to support your feet no matter their destination, the Larroudé Pavlova Ballet Flat will result in head turns from strangers, followed by compliments and queries as to its source. Just remember — it’s pronounced la-roo-day.

Margaux The Demi Flat

Designed in NYC and handmade in Spain, Margaux’s Demi can be precisely tailored to your preferences: with its impressive range of shades, widths, and textures (not to mention adjustable dimensions, as provided by a handy-slash-cutesy cord bow). The shoe’s upper takes advantage of Nappa leather’s luster and suppleness, while that five-millimeter padding establishes the sense of walking on clouds — something you’d associate more closely with a walking sneaker than with a minimalist ballet flat. Transcending momentary obsessions and seasonal shifts, the Demi is able to become anyone’s everyday companion, from the morning coffee run to the fancy dinner outing after work.

All in all: It marvelously balances classiness and wearability with customization, to the point of acting as fashion’s great equalizer (if not in price then at least in its vast optionality).

M.Gemi The Una Flat

You’re already aware of the fact that M.Gemi lets true Italian craftsmanship shine in its footwear lineup, while keeping a finger on the pulse of modern form and function. The Una, proof of concept, has earned me multiple compliments with its understated yet outside-the-box design that I could easily transition from summer to fall (and from day to night).

The pièce de résistance is a crisscrossing strap that bestows a luxe twist upon the black flat — enough to instantly elevate any getup. Its butter-evoking, unstructured leather, meanwhile, cradles the foot snugly and is thus a godsend for your busiest days.

All in all: You’re staring at a gorgeous, ultralight, and versatile shoe that came out on top after our team’s extensive flats testing. But don’t just stare — do something about it.

Vivaia Margot 3.0 Flat

Vivaia‘s overarching mission? To prove that style and comfort can coexist peacefully in the 21st century when it comes to what you put on your feet. The Margot 3.0 is optimized for wide feet in particular and is actually the roomiest pick on our list. To make matters better, this sensible shoe boasts triple-layer cushioning, responsive arch support marked by high-rebound PU foam, and an upgraded forefoot that will benefit wearers with bunions.

The reimagined Margot’s insole is also infused with Chinese mugwort, lauded for its antimicrobial properties. When my mom tested it, she required absolutely no break-in period and reported being charmed by the flat’s distinctive weave — working hand in hand with that squared-off cap toe.

All in all: This popular, reliable-as-can-be flat is best for women with wide feet and those operating within the constraints of a budget.

Anonymous Copenhagen Rhina Flat

The Copenhagen-based brand Anonymous, previously sported by none other than Olivia Rodrigo, is vying to become your next footwear go-to. The Rodrigo-vetted Rhina turns ballet flats’ iconic bow placement on its head, literally, and is reinforced by an elastic strap in an additional allusion to dance. A lambskin leather upper contributes to the shoe’s silk-like shine, just as a non-slip sole (trust me, I checked) makes every footfall a treat, not a chore. Like other prized selections on today’s footwear market, the Rhina was manufactured in Portugal.

All in all: If you’re seeking a women’s flat with a “IYKYK” energy and are fine with incessant, curiosity-driven questions, look no further than Anonymous Copenhagen’s Rhina.

Birdies Hummingbird Flat

This is what Mary Jane would look like if she let herself have more fun. Birdies, whose philosophy is rooted in translating the feel of indoor slippers to its assortment of flats, has put out a style named Hummingbird that hits all the high notes. Here, a showstopping, cognac-and-pink color palette combines sumptuousness with playfulness, while grosgrain binding keeps things in the realm of the polished and a velvet finish turns the Hummingbird into a must-have for fall.

In my experience, the shoe’s exterior is prone to taking on an almost three-dimensional quality depending on the angle of the light that hits it. I was also pleasantly surprised by the company’s so-called Barefoot Ballerina innovation — essentially, a “satin-lined sock that bends with you as if you are barefoot but still offers full arch support and seven layers of cloud-like comfort,” per Birdies. For someone who wears a lot of basics, the Hummingbird was a welcome wake-up call.

All in all: If your autumnal style could use a statement piece, make it the Birdies Hummingbird Flat, which doesn’t sleep on utilitarian features while being unabashedly maximalist.