Travel in Style With Our Picks for the Best Dressy Flats (2024)

It’s not hard to see why The Demi scored a perfect rating across every category in our testing of the very best dressy flats money can buy. Available in 14 varieties from matte and metallic to patterned and hand-woven, these versatile flats with a touch of foam make staying chic and comfortable on the road a breeze. In testing, we wore them everywhere with complete comfort and ease multiple times a week for up to eight hours at a time, from shopping to the office and everything in between. We owe that in part to the luxurious, flexible leather sole that adds not just a stylish look, but a supportive and durable feel while walking on cement, concrete, and varying terrain.

While any pair of fresh ballet flats can inspire a sense of blister-induced dread, these instantly quelled our fears. That cute bow contributing to their dainty nature? More than just a pretty face: they serve to personalize the fit of the shoe so you can loosen or tighten them as you see fit, thus helping prevent blisters, rubbing, or that uncomfortable sensation of your feet drowning in the footbed with each step. Given their unmatched quality, versatility, fit, timeless design, and comfort, we don’t hesitate to recommend these stunning flats for (nearly) any occasion.

The Details: 3 to 14 | Leather, foam

The ever-versatile Aerosoles Big Bet Ballet Flats simply make for a great bet with gold-toned chain-link hardware that allows you to rock them on dressier occasions, 17 unique colorways, and availability in wide sizing to accommodate swelling and feet of all shapes and sizes. Cushioning is one of the top features we prioritize in a ballet flat (after all, it helps offset some of the rigidness we commonly associate with flats while lending them a sneaker-like feel), and these flats really topped the charts in the comfort department thanks to a solid amount of cushioning at the insole.

One of our team members who requires footwear cushioning due to a previous foot surgery tried these out and found the comfort levels off the charts. We also thought the cushioning helped minimize stickiness and sweat that tends to accumulate with traveling or walking around for long periods. While wearing them for a few hours at a time on various types of terrain (walking and standing on both concrete and grass), we found these flats boast a softness that doesn’t contribute to blisters, stays put on the foot, and feels flexible with each step. Contributing to their supportive qualities is a textured rubber outsole that’ll allow you to feel secure on all types of flooring.

The Details: 5 to 12 | Leather, rubber

If you’re going to be spending a pretty penny on a pair of flats (say that 10 times fast), they should absolutely live up to the task of keeping you comfortable. Luckily, that’s exactly what these handmade beauties proved to do in testing. Thanks to their wide rubber band, they boast an on-trend look while keeping your foot fully secured, whether you’re walking around town or driving.

After a few wears, their leather outsole and lining became even more buttery soft, which made the entire wearing experience pain-free without any rubbing, blisters, or sliding around. While they’re not the most breathable flats (what else can you expect from Italian leather?), they kept our foot sweat at bay when we wore them for hours. Textured rubber at the outsole and a padded heel give these flats plenty of support and stability, which is why during testing, we compared them to a rock climbing shoe (in the best way possible) that you can totally wear with a skirt or dress. Unlike flimsier pairs, these chic flats prevent you from feeling any hard or uncomfortable flooring textures against the soles of your feet.

The Details: 35 to 42 | Leather, rubber

Packing for a business trip is a delicate art and science — after all, you want to put your best foot forward without ruining your best threads or shoes in your luggage. With these travel-friendly and oh-so-luxe dressy flats, you can literally have it all. In testing, we loved how the arch support completely supported the foot: walking around town, work, and even moving furniture felt like a total breeze. An elastic topline keeps the shoes secure whether you’re walking up or down stairs. They’re surprisingly breathable, too: we wore them on a hot day and never felt overheated, sweaty, or as if the flats were contributing to foot odor.

If your business trip is bound to include commuting from numerous places to another, you’ll love that these flats look dressy on the outside while feeling like sneakers from within. Vertical flexibility allows them to conform seamlessly to your foot with each step, while a rubber sole offers plenty of traction — even on stubborn slippery tile. The toebox is a cross between an almond and a pointed toe, offering the same flattering properties of a pointed toe with all the breathing room and comfort of a wider almond toe.

The Details: 5 to 12 | Leather, foam

There’s nothing like a sophisticated pair of flat sandals to take you from the beach to the boardwalk and even the boardroom. While lace-up sandals are notoriously tricky to wear (either the laces are too short or they tend to slide down), we found these to be the perfect flat pair. Not only does the Italian nappa leather feel luxe enough to prevent blisters, but these sandals also come with enough material to lace up several times over — complete with your choice of a bow, a knot, or a double knot — while resting firmly against the calf. Not to mention, they boast a gorgeous Greek goddess vibe that instantly upgrades any summer or travel outfit.

While several hours of walking on a flat sandal often yields foot pain, the addition of five millimeters of foam at the heel made them as comfortable to wear as sneakers during short walking distances. They mold to your foot with each step, and while they might not be your first choice for a day of power walking, they transition seamlessly from day to night — making them well worth the spend.

The Details: 3 to 14 | Leather, foam

Not sure what’ll be on the itinerary for the remainder of your trip, your workday, or your day off? Our top pick for the best versatile dressy flats will serve you well regardless of your plans. Boasting orthopedic-friendly elements like padding at the ball of the foot for cushioning and comfort, as well as an elastic band below the big toe for added range of motion and swelling accommodation, we appreciated how these pointed toe flats marry comfort and style. In testing, we found the flats fit snugly so as to keep your foot in place without making you feel suffocated or overly sweaty (we have the synthetic breathable lining to thank for that). Cut-outs and stretchy mesh at the sides of the foot further help promote ventilation to keep your feet dry while also lending them a dressy look. So dressy, in fact, that you can wear them for almost any occasion from a laid-back wedding to a day of running errands.

The Details: 6 to 12 | Leather, rubber

It’s not hard to see why these classic ballet flats have withstood the test of time, trends, and travels. Between their 15 cool colorways from muted lavender to trendy tan, their cinched ankle band for added support and stability, and their bendable construction and included dust bag ideal for packing in your carry-on, they truly offer so much to love. Chief among their stand-out properties is their lightweight, barely there feel. Whether running around completing errands or chasing after a toddler, these flats proved to be comfortable straight out of the box in testing — no break-in period required. Despite their weightlessness and midfoot flexibility, they boast a sturdiness conducive to all-day wear (but feel free to wear a thin sock or stocking to prevent sweat build-up). Adding to their versatility is the logo medallion at the toe box that gives it a touch of glamor without leaning too heavily on branding. So, while they’d totally work for a day at the office, you can easily wear them rushing out the door for a full day out on the town.

The Details: 4 to 12 | Leather, foam, rubber

Frequently Asked Questions

• How can you make flats more comfortable?

  First, ensure you grab the right size. While sizing up could technically accommodate for swelling, it’ll also increase the chance of rubbing against the lining. To prevent blisters associated with sweat, wear a thin sock or stocking to absorb moisture.

  We spoke with Dr. Daniel Geller, a board-certified podiatrist and Kane Footwear advisor, who says that "arch support isn’t only important in your running or athletic shoes. It’s also important in your flats.” He explains it’s widely known that arch support can help prevent several conditions like plantar fasciitis, Achilles tendinitis, Morton’s neuroma, and stress reactions, which can all compromise your gait, posture, and overall well-being.

  Other elements to look for include soft materials, cushioning, wide toe boxes to prevent crowding of the toes, and other orthopedic-friendly features suited to your unique needs.

• How do you pack flats?

  The best way to pack flats is to first ensure the cleanliness of the rest of your travel wardrobe. Do this by placing your flats into a separate packing cube, drawstring-lined bag, or tied plastic bag. The soles of your flats should be pressed up against one another so as not to further sully the interior of the bag. While there’s no avoiding having your shoes compressed within the weight of your luggage, they’ll usually return to their original shape within a couple hours once you take them out of the bag.

• How do you style flats?

  Looking stylish in flat shoes all depends on how you style them. Pair them with of-the-moment pieces like wide-leg trousers, tweed blazers, tailored high-waisted shorts, and “cottagecore” attire like ruffled babydoll dresses. Of course, the flats you select should also be understated enough to look effortless.

  “When dressy flats are simple and elegant, it’s much easier to wear them with everything, especially with your purses and jewelry as well,” says Bibeau.
  

The 9 Most Comfortable Flats of 2024, Tested and Reviewed