A woman wearing a sequined dress and VALENTINO GARAVANI Rockstud metallic leather ballet flats sits on a staircase, holding a white handbag adorned with a decorative logo. She gazes downward, her left foot resting on a lower step. These metallic ballet flats are among the best shoes to wear with long dresses. Ornate iron railings are visible in the background.

VALENTINO GARAVANI

The Dress Edit

From Flats To Boots, These Are The Best Shoes To Wear With Long Dresses

Fall has arrived, winter is on the way, and I’m on the lookout for all the best shoes to wear with long dresses. So, from flats to boots and sneakers to kitten heels, I’ve scrolled through thousands of pages of designer footwear to narrow it down. Below is my carefully curated edit of shoes I’ll wear with long dresses for the season ahead. Will you opt for a sleek pair of metallic sneakers and a stretch knit maxi dress on weekends? Or will it be a chic pair of flats and a structured maxi silhouette for stylish office days? Keep reading to find your new go-to shoes to style with every long dress you own…

A pair of feet wearing black CHRISTIAN LOUBOUTIN Mamastrapitina Mary Jane embellished pumps, adorned with small bows on the toes. The shoes feature large round black buckles on the straps, making them an ideal choice to pair with long dresses. The person is wearing a sheer black garment with small white polka dots.

CHRISTIAN LOUBOUTIN Mamastrapitina Ballerina Flats

A person wearing CHRISTIAN LOUBOUTIN Hibaq white leather strappy sandals—often considered the best shoes to wear with long dresses. They are seated with crossed legs, sporting light-colored, wide-legged pants. The background is dark, featuring a gradient effect.

NEOUS Ibor Leather Slingback Sandals

Kitten Heels & Flats Are The Best Shoes To Wear With Long Dresses On Off Duty Days

I’m calling it, when it comes to off-duty dressing, flats and sneakers are the best shoes to wear with long dresses. And, since I feel better and relax more when I successfully combine style and comfort, these shoe and dress pairings couldn’t be more perfect! Firstly, I highly recommend adding the Mamastrapitina ballerina flats by Christian Louboutin to your cart before they inevitably sell out. Secondly, pair them with the Nami sweater dress by Veronica Beard and the metallic woven Hollis tote by Anthropologie. The ultimate weekend brunch date outfit, I predict you’ll be wearing these pieces on repeat throughout fall and winter.

Additionally, the Ibor leather slingback sandals by Neous will elevate any ankle-length, after-dark outfits that you have planned this fall. Choose a chic maxi dress like the Manuela bow slip maxi dress by Loveshackfancy and a top handle bag to tie the look together. I highly recommend the statement embellished Loco leather bag by Valentino Garavani. Like the outfit above, these versatile pieces are perfect for a capsule closet and will remain in style for years to come.

Shop more of the best shoes to wear with long dresses selected and reviewed by our expert fashion buyers and stylists

  • CHLOÉ Eve Thigh High Boot

    $2,090
  • CHRISTIAN LOUBOUTIN Santia Pointed Toe Knee High Boot

    $2,195
  • GUCCI Pointed Toe Booties

    $1,790
  • CHRISTIAN LOUBOUTIN Mamastrapitina Ballerina Flats

    $1,195
  • AQUAZZURA So Nude Leather Sandals

    $795
  • AQUAZZURA Snake-Embossed Slingback Pumps

    $895
  • PRADA Mordore Nappa Heeled Sandals

    $1,220
  • AQUAZZURA Mayor 35 Mary Jane Pumps

    $1,250
  • VALENTINO GARAVANI Bowjane Mary Jane Flats

    $1,650
  • SAINT LAURENT Vicky 90 Ankle Boots

    $1,590
  • GOLA Badminton Court Sneakers

    $80
  • P448 Monza Sneakers

    $345
  • VAGABOND SHOEMAKERS Vagabond Flats

    $130
  • GOLDEN GOOSE Ballstar Sneakers

    $595
  • GIANVITO ROSSI Linsay Ankle Boots

    $1,895
  • NEOUS Ibor Leather Slingback Sandals

    $650
  • ROGER VIVIER Buckle-embellished Sequined Metallic Leather Slingback Pumps

    $1,125
  • VERSACE Medusa-plaque Metallic Ballerina Shoes

    $925
  • MIU MIU Buckled Leather Ballerina Shoes

    $1,050
  • GOLA Elan Sneakers

    $110
  • AMINA MUADDI Ane Crystal-embellished Leather Ballet Flats

    $1,345
  • SAM EDELMAN Miranda Mary Jane Flat

    $130
  • SAINT LAURENT 110mm Vendome Leather Buckle Boots

    $1,950
  • VALENTINO GARAVANI Rockstud metallic leather ballet flats

    $950
  • BALENCIAGA Beige 3XL Sneaker

    $1,150
  • GOLA Torpedo Sneakers

    $125
  • GIANVITO ROSSI Carla Mary Jane Ballet Flat

    $745
  • GOLDEN GOOSE Ballstar Distressed Leather Sneakers

    $565
  • AMINA MUADDI Fiona Suede Boots

    $1,375
  • MANOLO BLAHNIK Garder 45 Velvet Knee Boots

    $1,275

Flats Or Boots? Choosing The Best Smart Shoes To Wear With Long Dresses

I’m all about designer boots when it comes to the best shoes to wear with long dresses in the fall. In particular, the Linsay ankle boots by Gianvito Rossi. Boots like these will never go out of style. Plus, they’ll go with every long dress you own making them look instantly chicer. On top of this, they’ll stave off the impending chill and look amazing in the process. Add these boots to your cart before they inevitably sell out. Then, style them with Balenciaga’s ribbed knit turtleneck maxi dress and the mini La Medusa top handle bag by Versace for maximum weekend style points this fall and beyond.

As for heels? Don’t get me wrong, they can totally work with long dresses. Especially if we’re talking about gowns. However, if we’re talking about the best shoes to wear with long dresses for less dressy dress codes, I opt for embellished flats every time. This chic combination of an ankle-length or floor-sweeping silhouette and statement embellishments never fails. For example, try the gathered midi dress by Victoria Beckham with the Ane crystal-embellished ballet flats by Amina Muaddi. Add the Le City small bag by Balenciaga to complete this effortlessly stylish ensemble. It’s the perfect outfit for low-key dinner dates and any other weekend evening plans where you want to feel your most put-together self.

Shop All Of The Best Shoes To Wear With Long Dresses

A person wearing beige pants and GIANVITO ROSSI Linsay dark brown buckled ankle boots, often considered among the best shoes to wear with long dresses, sits cross-legged on a grey ledge. The boots feature a pointed toe, a side zipper, and a decorative strap around the ankle.

GIANVITO ROSSI Linsay Ankle Boots

A person wearing a black sheer dress and sitting on a concrete ledge showcases the ideal footwear for long dresses: AMINA MUADDI Ane black crystal-embellished ballet flats. These sophisticated shoes feature crisscrossing straps that elegantly wrap around the ankles. The person is also holding a black clutch adorned with matching silver studs.

AMINA MUADDI Ane Crystal-embellished Leather Ballet Flats

Upgrade Your Office Wardrobe: Learn How To Style Flats For Work