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Dressy Flats To Wear With A Cocktail Dress

dressy flats you can wear with a cocktail dress, formal flats
From top to bottom: Bells & Becks $375, Prada $1,120 $672, Rebecca Allen $175, Dee Ocleppo $255 $178

If you want to wear a cocktail dress with flats, I am here for you. From foot ailments and sprained ankles to rocky terrain and a general intolerance for discomfort, many of my clients are requesting dressy flats (aka evening flats) for their party looks this season. When it comes to wearing flats with a cocktail dress, it’s all about picking the right dress length and complementary flats for the occasion. Let’s get to it…

Can You Wear Flats With A Cocktail Dress?

We all love that lean long line a high heel gives us, but you can in fact wear a cocktail dress with flats and still achieve a slim silhouette. The key to pulling off a cocktail dress with evening flats is the dress length. The dress either needs to be a maxi dress or a mini dress. A mini dress will make your legs look loooong. A maxi dress will give you that long line too as well as partially hide dressy flats and take them out of the spotlight. When wearing dressy flats with a maxi dress, you want to wear the simplest of the dressy flats below. You don’t want an embellishment catching on the hem of your dress.

Requirements For Chic Dressy Flats

Wearing flats with a cocktail dress or fancy pants can go terribly wrong if you choose the wrong flats. They really have to be an excellent pair. When picking your flats for evening wear, choose ones that have:

  1. A pointed toe, peep toe, or elongated square toe
  2. A rich color or shiny texture
  3. A smooth or seemingly smooth texture

To see these requirements in action, scroll down and behold your choices.

Bonus Tip: For extra comfort, you can even have a cobbler replace the soles of your flats with a more comfortable, non-slip option or add supportive insoles.

Evening Flats With Dress Pants

You don’t always have to wear dresses to parties and formal events. I am constantly putting my clients in dressy ankle pants or ankle-length jumpsuits for events. I say ankle length because longer pants are not flattering with flat shoes. And you generally want to have a slim pant leg rather than a wide pant leg. If you do prefer a wider pant leg, go for a cropped look with your dressy flats, and keep in mind a pointy toe flat is always more flattering than a rounder toe. If comfort requires you to wear a rounder toe, a slim ankle length pant will look best versus a wider pant leg or a dress.

Steve Madden Elina Crystal Bow Ballet Flat

dress flats you can wear with a cocktail dress
Steve Madden $89.95 $52.99

Available at Amazon.

Sizing: 5.5-11M

Material: Textile upper, synthetic lining and sole

Prada Loop Bouquet Pointed Toe Flat

dressy flats for formal occasions
Prada $1,120

Available at Nordstrom and Neiman Marcus.

Sizing: 5-11M

Material: Leather upper, lining and sole

Rothy’s The Point in Solid Black

flats you can wear with a cocktail dress
Rothy’s $149

I am a big fan of Rothy’s flats and this shoe in black is my go-to dressy flat (the other colors are usually too casual looking for a cocktail dress code). On top of having such a chic pointed toe, they’re made of recycled plastic bottles and are machine washable. I recently paired them with a lady’s tuxedo for a client and it was the perfect dressy, yet comfortable flat. Read my full Rothy’s review, here.

Available at Rothy’s.

Sizing: 5-13M, runs small; order half size up

Material: Knit with 100% recycled materials

Franco Sarto Racer Ankle Strap d’Orsay Pointed Toe Flat

evening flats
Franco Sarto $79.99

Available at Nordstrom and Zappos.

Sizing: 5-11M

Material: Synthetic upper and lining, rubber sole

Badgley Mischka Fergie Pointed Toe d’Orsay Flat

dressy flats
Badgley Mischka $198 $49.52

Available at Amazon and Zappos.

Sizing: 5-11M

Material: Textile upper, synthetic and textile lining, leather sole

Dee Ocleppo Pretty Velvet Crystal Bow Ballerina Flats

evening flats that go with formal wear
Dee Ocleppo $255 $178.50

Available at Saks Fifth Avenue and Farfetch.

Sizing: 5-11M

Material: Leather outsole and lining

Rebecca Allen The Skim Flat

Dressy Flats
Rebecca Allen $175

Available at Nordstrom, Amazon, and Macy’s.

Sizing: 6-10M

Material: Leather upper, lining and sole

Zigi Bibiana Flat

dressy flats
Zigi $179.95

Available at Nordstrom.

Sizing: 6-10M, whole sizes only; for 1/2 sizes, order the next size up

Material: Leather upper, lining and sole

Sam Edelman Wanda Pointed Toe Flat

flats you can wear with a cocktail dress
Sam Edelman $94.97

Available at Amazon and Zappos.

Sizing: 5-12M

Material: Synthetic, textile or leather upper, synthetic lining and sole

Linea Paolo Diana Slingback Pointed Toe Flat

dressy flats you can wear with a cocktail dress
Linea Paolo $119.95 $83.96

Available at Nordstrom and Amazon.

Sizing: 4.5-13M

Material: Leather upper, synthetic lining, rubber sole

Rothy’s The Point in Black Shimmer

dress flats
Rothy’s $149

Available at Rothy’s.

Sizing: 5-13M, runs small; order half size up

Material: Knit with 100% recycled materials

Here’s another pair of Rothy’s with a subtle shimmer that will go beautifully with a cocktail dress or dressy pants. Read my full Rothy’s review, plus tips on how to wash them, here.

Badgley Mischka Collection Natalia d’Orsay Flat

evening flats you can wear with a cocktail dress
Badgley Mischka $149.99 $117.49

Available at Amazon.

Sizing: 5-11M, runs small, consider ordering a size up

Material: Leather

Dressy Flats For Cocktail Dresses From Years Past

dress flats you can wear with a cocktail dress
From top to bottom: Steve Madden $89.95, Sarto by Franco Sarto $120, Santoni $695 $382.25, Linea Paolo $119.95

I originally wrote this post years ago and update it regularly due to its popularity. I’ve left these photos below for nostalgic purposes. Whenever I update older posts, I love to hold on to a collection of images as a bit of a time capsule so we can watch how our style evolves.

Jessica Rich Women’s Alea Pointed Toe Slip On Flats

evening flats you can wear with a dress
Jessica Rich $215

These flats are available at Bloomingdale’s and Nordstrom.

Sizing: 5-12M

Material: Mesh fabric upper and lining, leather sole

Bells & Becks Lia Pointed Toe Flat

evening flats
Bells & Becks $375

Sizing: 6.5-10M

Material: Leather upper, lining and sole

Margaux The Mesh Pointe

evening flats you can wear with a cocktail dress
Margaux $245

Sizing: 3-14, available in medium, narrow or wide

Material: Mesh upper with Italian suede trim and leather lining

Nine West Blaha Half d’Orsay Pointed Toe Flat

dressy flats
Nine West $89

These flats are available at Macy’s, Nine West, and Nordstrom.

Sizing: 5-12M

Material: Leather upper/synthetic lining and sole

Santoni Slingback Pointed Toe Flat

evening flats you can wear with a cocktail dress
Santoni $695 $382.25

Sizing: EU35.5-41M

Material: Leather upper, lining and sole

Aeyde May Pointed Toe Flat

flats you can wear with a cocktail dress
Aeyde $295

Sizing: 6-12M

Material: Leather upper, lining, and sole

Badgley Mischka Collection Saga Embellished Slingback Flat

dress flats you can wear with a cocktail dress
Badgley Mischka Collection $235 $140.47

These flats are available at Zappos, and Bloomingdale’s.

Sizing: 6.5-10M

Material: Satin fabric upper, manmade lining, leather sole

Sarto by Franco Sarto Tracy Flat

dress flats you can wear with a cocktail dress
Sarto by Franco Sarto $130

These flats are available at Nordstrom, Zappos, Franco Sarto, Dillard’s, and Amazon.

Sizing: 4-13M

Material: Leather upper and lining, synthetic sole

Naturalizer Kirsten Asymmetric Pointed Toe Flat

dressy flats you can wear with a cocktail dress
Naturalizer $135 $109.99

This flat is available at Naturalizer, DSW, Macy’s, and Zappos.

Sizing: 6-12, available in medium and wide

Material: Leather, metallic leather or suede upper with a pointed toe

Linea Paola Niche Pointed Toe Flat

dress flats you can wear with a cocktail dress
Linea Paola $139.95

These flats are available at Nordstrom and Amazon.

Sizing: 4-13M

Material: Leather upper, synthetic lining, rubber sole

Beverly-feldman-prosecco

Beverly Feldman $111

Costume-national

Costume National $477

Vera-wang-flat

Vera Wang $96

Vaneli

Vaneli $124

Gabriella-rocha-daisi

Gabriella Rocha $52.47

 

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