Dressy Flats To Wear With A Cocktail Dress

If you need 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. 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.

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

These flats are available at Nordstrom and Macy’s.

Sizing: 5.5-11M

Material: Textile upper, synthetic lining and sole

Jessica Rich Women’s Alea Pointed Toe Slip On Flats

These flats are available at Bloomingdale’s and Nordstrom.

Sizing: 5-12M

Material: Mesh fabric upper and lining, leather sole

Prada Loop Bouquet Pointed Toe Flat

These flats are available at Nordstrom, Saks Fifth Avenue, Bergdorf Goodman, and Neiman Marcus.

Sizing: 5-11M

Material: Leather upper, lining and sole

Rothy’s The Point in Solid Black

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.

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

These flats are available at Nordstrom, Zappos and Franco Sarto.

Sizing: 5-11M

Material: Synthetic upper and lining, rubber sole

Badgley Mischka Fergie Pointed Toe d’Orsay Flat

These flats are 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

These flats are available at Neiman Marcus, Saks Fifth Avenue, and Farfetch.

Sizing: 5-11M

Material: Leather outsole and lining

Rebecca Allen The Skim Flat

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

Sizing: 6-10M

Material: Leather upper, lining and sole

Bells & Becks Lia Pointed Toe Flat

Sizing: 6.5-10M

Material: Leather upper, lining and sole

Margaux The Mesh Pointe

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

Material: Mesh upper with Italian suede trim and leather lining

Zigi Bibiana Flat

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

Material: Leather upper, lining and sole

Nine West Blaha Half d’Orsay Pointed Toe Flat

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

Sizing: 5-12M

Material: Leather upper/synthetic lining and sole

Sam Edelman Wanda Pointed Toe Flat

These flats are available at Nordstrom, Zappos, and Amazon.

Sizing: 5-12M

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

Badgley Mischka Collection Natalia d’Orsay Flat

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

Material: Leather

Linea Paolo Diana Slingback Pointed Toe Flat

These dressy flats are available at Nordstrom, Amazon, and Linea Paolo.

Sizing: 4.5-13M

Material: Leather upper, synthetic lining, rubber sole

Rothy’s The Point in Black Shimmer

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.

Dressy Flats For Cocktail Dresses From Years Past

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.

Santoni Slingback Pointed Toe Flat

Sizing: EU35.5-41M

Material: Leather upper, lining and sole

Aeyde May Pointed Toe Flat

Sizing: 6-12M

Material: Leather upper, lining, and sole

Badgley Mischka Collection Saga Embellished Slingback Flat

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

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

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

These flats are available at Nordstrom and Amazon.

Sizing: 4-13M

Material: Leather upper, synthetic lining, rubber sole

Beverly Feldman $111

Costume National $477

Vera Wang $96

Vaneli $124

Gabriella Rocha $52.47