Flattering Dresses to Wear No Matter Your Age or Taste (2024)

Table of Contents
Cult Favorite Most Flattering co*cktail Dress Fit & Flare Best for Work Sultry Lace OG Wrap Dress Versatile Knit Pop of Purple One-Shoulder Better Than Basic The Somerset Collection by Anthropologie The Somerset Maxi Dress The Somerset Collection by Anthropologie The Somerset Maxi Dress Dress the Population Catalina Fit & Flare Dress Dress the Population Catalina Fit & Flare Dress Mac Duggal Long Sleeve Fit & Flare Velvet Embellished co*cktail Dress Mac Duggal Long Sleeve Fit & Flare Velvet Embellished co*cktail Dress Black Halo Women's 3/4 Sleeve Jackie O Dress Black Halo Women's 3/4 Sleeve Jackie O Dress MEROKEETY Sleeveless Lace Floral co*cktail Dress MEROKEETY Sleeveless Lace Floral co*cktail Dress Diane von Furstenberg Jeanne Silk Jersey Wrap Dress Diane von Furstenberg Jeanne Silk Jersey Wrap Dress Everlane The Ribbed Wrap Midi Dress Everlane The Ribbed Wrap Midi Dress Ralph Lauren Surplice Jersey Dress Ralph Lauren Surplice Jersey Dress Norma Kamali Diana Gown Norma Kamali Diana Gown Spanx The Perfect A-line 3/4 Sleeve Dress Spanx The Perfect A-line 3/4 Sleeve Dress Tuckernuck Faven Dress Tuckernuck Faven Dress Vince Camuto Animal Print Long Sleeve Midi Dress Vince Camuto Animal Print Long Sleeve Midi Dress Brochu Walker The Havana Dress Brochu Walker The Havana Dress La Femme Off the Shoulder Beaded Satin Trumpet Gown La Femme Off the Shoulder Beaded Satin Trumpet Gown Lafayette 148 New York Harpson Finesse Crepe Sheath Dress Lafayette 148 New York Harpson Finesse Crepe Sheath Dress Banana Republic Cece Knit Wrap Dress Banana Republic Cece Knit Wrap Dress Roksanda Demetria Caped Midi Dress Roksanda Demetria Caped Midi Dress Billy Reid Turtleneck Sweater Dress Billy Reid Turtleneck Sweater Dress Tuckernuck Navy Tweed Jackie Dress Tuckernuck Navy Tweed Jackie Dress Frank & Eileen Distressed Vintage Wash Frank & Eileen Distressed Vintage Wash References
Flattering Dresses to Wear No Matter Your Age or Taste (1)

Every item on this page was chosen by a Town & Country editor. We may earn commission on some of the items you choose to buy.

PSA: Just because you've reached a certain age doesn't mean you have to limit your wardrobe choices. Women over 50 can and should be able to flaunt their frames in body-skimming styles, and one of the best ways to do so is in a dress. Whether you've been invited to a wedding this winter or you're looking for something to wear to work, there's a silhouette for every age, style, and body shape. From figure-hugging wrap dresses to fit-and-flare co*cktail dresses, here are the most flattering dresses to wear this season and beyond.

Cult Favorite

The Somerset Collection by Anthropologie The Somerset Maxi Dress

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Cult Favorite

The Somerset Collection by Anthropologie The Somerset Maxi Dress

Strategic shirring at the waist brings out the hourglass in any figure, while a blue geometric print proves that dresses with coverage need not be boring. The maxi is also available in velvet, which just so happens to be .

Size Range: XS-3X

Colors: 7+

Material: Cotton

Most Flattering co*cktail Dress

Dress the Population Catalina Fit & Flare Dress

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Most Flattering co*cktail Dress

Dress the Population Catalina Fit & Flare Dress

The fitted top of this breezy dress highlights your arms and shows off your waist without constricting your movement: ideal for a night of drinks and dancing.

Size Range: XXS-XXL

Colors: 15

Materials: 95% Polyester, 5% Spandex

Fit & Flare

Mac Duggal Long Sleeve Fit & Flare Velvet Embellished co*cktail Dress

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Fit & Flare

Mac Duggal Long Sleeve Fit & Flare Velvet Embellished co*cktail Dress

The maximalist's version of the modest co*cktail dress. Need we say more?

Size Range: 0-12

Colors: Black

Material: 100% Polyester

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Best for Work

Black Halo Women's 3/4 Sleeve Jackie O Dress

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Best for Work

Black Halo Women's 3/4 Sleeve Jackie O Dress

A folded neckline add visual interest and a hint of allure to an otherwise classic sheath style.

Size Range: 0-14

Colors: 5

Materials: 95% Polyester, 5% Spandex

More: The Best Work Dresses for Women

Sultry Lace

MEROKEETY Sleeveless Lace Floral co*cktail Dress

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Flattering Dresses to Wear No Matter Your Age or Taste (18)

Sultry Lace

MEROKEETY Sleeveless Lace Floral co*cktail Dress

Now 24% Off

Lace adds instant sex appeal, proving a knee-length dress can be just as sultry as a mini.

Size Range: S-XL

Colors: 15+

Materials: 65% Rayon, 35% Polyester

OG Wrap Dress

Diane von Furstenberg Jeanne Silk Jersey Wrap Dress

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OG Wrap Dress

Diane von Furstenberg Jeanne Silk Jersey Wrap Dress

Diane von Furstenberg made her name on her signature wrap dress, and for good reason—it's timelessly stylish and looks great on practically everybody.

Size Range: 00-16

Color: Black & White

Material: 100% Silk

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Versatile Knit

Everlane The Ribbed Wrap Midi Dress

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Versatile Knit

Everlane The Ribbed Wrap Midi Dress

A wrap-style sweater dress is a great anytime option—style it with pair of slouchy boots or loafers for a casual look that's still stylish, or pair it with heels for a night out.

Size Range: XXS-XL

Colors: Black, Green

Materials: 65% Viscose, 35% Recycled Nylon

Pop of Purple

Ralph Lauren Surplice Jersey Dress

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Pop of Purple

Ralph Lauren Surplice Jersey Dress

Ralph Lauren calls this "the perfect everyday dress," and they're not wrong. A V-neckline shows a bit of skin while a self-tie sash accentuates the waist for a polished fit.

Size Range: 00-18

Colors: 4

Materials: Polyester, Elastane

One-Shoulder

Norma Kamali Diana Gown

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One-Shoulder

Norma Kamali Diana Gown

Ruching all the way down the sides of this one-shoulder dress allows it to hug your curves perfectly while also disguising any areas you'd rather not highlight.

Size Range: XXS-XL

Colors: 25+

Materials: 95% Polyester, 5% Spandex

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Better Than Basic

Spanx The Perfect A-line 3/4 Sleeve Dress

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Better Than Basic

Spanx The Perfect A-line 3/4 Sleeve Dress

The perfect knee-length dress doesn't exi... Oh wait, it actually does. Featuring 3/4 sleeves and an A-line fit that nips at the waist, Spanx's dress is made of a smoothing fabric that looks beyond flattering on all body shapes and can transition effortlessy from work to play.

Size Range: XS-3X

Colors: Black, Navy

Material: Ponte Fabric

Polka-Dot Fun

Tuckernuck Faven Dress

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Polka-Dot Fun

Tuckernuck Faven Dress

When in doubt, go for polka-dots. While you're at it, throw on a pair of spectator shoes. Very Kate Middleton of you.

Size Range: XXS-XXXL

Colors: Black & White

Materials: 100% Polyester (outer), 97% Polyester, 3% Spandex (lining)

Fierce Spots

Vince Camuto Animal Print Long Sleeve Midi Dress

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Fierce Spots

Vince Camuto Animal Print Long Sleeve Midi Dress

A leopard print is a fun fashion "do" at any age.

More: Stylish Leopard Print Coats to Be Spotted in This Season

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T&C Approved

Brochu Walker The Havana Dress

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T&C Approved

Brochu Walker The Havana Dress

Add some dimension to your look with Brochu Walker's puff-sleeved maxi shirt dress. It comes in a rainbow of colors for all seasons, like this burnt siena, and a great year-round layering piece. T&C Associate Shopping Editor Sophie Dweck calls it "the most versatile wardrobe staple you'll ever own." Wear it with a belt for a figure-flattering look or loose to keep things easy breezy—you'll look chic either way.

Size Range: XS-L

Colors: 15+

Materials: 65% Polyester, 35% Cotton

For Formal Affairs

La Femme Off the Shoulder Beaded Satin Trumpet Gown

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For Formal Affairs

La Femme Off the Shoulder Beaded Satin Trumpet Gown

For formal affairs, the portrait neckline is uber sophisticated. Also, notice the beaded details on the sleeves and at the back! A show-stopping dress if we do say so ourselves.

Size Range: 0-18

Colors: Navy

Material: 100% Polyester

Staple Sheath Dress

Lafayette 148 New York Harpson Finesse Crepe Sheath Dress

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Staple Sheath Dress

Lafayette 148 New York Harpson Finesse Crepe Sheath Dress

Work, weekend, wedding invites—whatever you schedule throws at you, this figure-friendly sheath dress has your back.

Size Range: 2-18

Colors: Black, Purple

Material: Acetate/Polyester

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Neutral Upgrade

Banana Republic Cece Knit Wrap Dress

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Neutral Upgrade

Banana Republic Cece Knit Wrap Dress

The mossy hue on this mid-length asymmetrical dress makes for a nice change from the usual black and navy.

Size Range: XXS-XXL

Colors: 3

Material: 86% Viscose Rayon, 14% Polyester.

Bring the Drama

Roksanda Demetria Caped Midi Dress

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Bring the Drama

Roksanda Demetria Caped Midi Dress

A bold color and femme cape team up for a dress that positively screams "drama."

Size Range: 2-14

Colors: 1

Material: 34% Silk, 66% Viscose

Elegant Sweater Dress

Billy Reid Turtleneck Sweater Dress

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Elegant Sweater Dress

Billy Reid Turtleneck Sweater Dress

Now 50% Off

This merino wool dress will not only keep you warm in these cold temps, but its neckline and fit-and-flare shape will have you looking elegant as can be.

Size Range: XXS-XXL

Colors: Brown

Materials: 100% Merino Wool

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Timeless Tweed

Tuckernuck Navy Tweed Jackie Dress

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Timeless Tweed

Tuckernuck Navy Tweed Jackie Dress

Take the tweed trend for a spin this season with a timeless Jackie O-inspired mini.

Size Range: XXS-XXXL

Colors: 10+

Material: 100% Polyester

Denim Dress

Frank & Eileen Distressed Vintage Wash

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Denim Dress

Frank & Eileen Distressed Vintage Wash

An easy, breezy denim shirt dress is guaranteed to be something you reach for all the time once the weather starts heating up.

Size Range: XXS-XL

Washes: 6

Material: 100% Italian Cotton

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Lauren Hubbard

Writer

Lauren Hubbard is a freelance writer and Town & Country contributor who covers beauty, shopping, entertainment, travel, home decor, wine, and co*cktails.

Flattering Dresses to Wear No Matter Your Age or Taste (2024)

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