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14 Classic Dresses Every Woman Should Own

Build up your wardrobe with these timeless shapes that you'll keep in your closet for years.

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Sarin Mathews Womens Off The Shoulder Short Sleeve High Low Cocktail Skater Dressvia


There’s a reason black is the classic color for a night out: it’s slimming, hard to stain, and easy to accessorize. Add a pop of color to your little black dress with accessories and bold lipstick, or keep it simple with black flats. Here are more slimming outfit tricks.

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Lark & Ro Women's Cap Sleeve Faux Wrap Sheath Dressvia

Sheath dress

The beauty of a sheath dress is that it’s polished yet sexy, meaning it can make a smooth transition straight from work to a night out. Go for basic black, or pick a bold color and print that stands out.

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GRACE KARIN Boatneck Sleeveless Vintage Tea Dress with Beltvia

A-line dress

The classic A-line dress has stood the test of time. It flatters nearly every body type, and it works on women of any age.

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LONGYUAN Women's Summer Casual T Shirt Dresses Swimsuit Cover Ups with Pocketsvia


Nothing says summer like a cute frock. It can transition straight from the beach to a fancy dinner by swapping out flip-flops for heels and adding some sparkly accessories. When fall’s cool temperatures roll around, throw on a cardigan and tights to keep it appropriate through the seasons. Investing in a classic piece of clothing like a sundress might be one of the 51 fashion tips a personal stylist won’t tell you for free.

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PrettyGuide Women 's 1920s Black Sequin Gatsby Maxi Long Evening Prom Dressvia

Evening gown

You might rarely pull this one out, but you’ll want one on hand for any galas or black-tie weddings. Look for one with a classic cut that’s not too memorable so you can repeat it at different events, and just change up the accessories.

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AlvaQ Women's Sexy V Neck Sleeveless Lace Dressvia

Cocktail dress

For those evenings when you want something a step above your usual look, you’ll want to pull on a cocktail dress that makes you feel sultry and confident. Like your go-to gown, let the accessories do the talking with a dress that blends in so you can wear it over and over.

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Zredurn Women’s Elegant Pleated Shirt Dress with Long Sleeve Pleated Belted A-Line Dress Stylevia


Wear one with sandals for a casual weekend warrior look, or throw on a blazer and polished heels to dress it up for the office. It’s a timeless look that you’ll never want to get rid of.

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BTFBM Women’s 2019 Casual Crew Neck Ruched Stretchy Bodycon T Shirt Short Mini Dressvia

T-shirt dress

For a laidback look, slip on a breezy T-shirt dress. It’s as comfy as sweatpants, but you’ll look put-together when you run to the grocery store. Not being able to dress comfortably could be of the 15 annoying fashion problems every woman will definitely understand.

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ZESICA Women's Bohemian Floral Printed Wrap V Neck Short Sleeve Split Beach Party Maxi Dressvia


A floor-length ensemble is classy and fresh. A sleeveless option is cool and breezy in the summer, but adding a jacket or sweater makes it a comfy option all year long.

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v28 Women Cowl Neck Knit Stretchable Elasticity Long Sleeve Slim Fit Sweater Dressvia

Sweater dress

For cold days when restricting pants sound miserable, a sweater dress should be your go-to. Pair it with tights and riding boots, and you’ll stay cozy in the chilliest temperatures.

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Sidefeel Women Cute V Neck Sweet Scallop Pleated Skater Dressvia

Fit and flare dress

The fitted top and flared skirt are universally flattering, but this shape is also a master of versatility. Depending on how you accessorize it, you can wear it straight from lunch with grandma to a dinner date.

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HOMEYEE Women's Sleeveless Cocktail A-Line Embroidery Party Summer Wedding Guest Dress A079via

Go-to party dress

For a night out, you’ll want a never-fail dress that you feel confident in. Find one with a classic silhouette that can look either casual or dressy so you never have to worry about feeling under- or overdressed. Don’t miss these fashion upgrades that make you look expensive.

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Twinklady Women's 3/4 Bell Sleeve Floral Lace Elegant Cocktail Party A-Line Mini Dressvia

Lace dress

A white lace dress looks fun and flirty, while a black lace is glamorous and sexy. Either way, the frills add a little something special to an otherwise basic frock.

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GLUDEAR Women's 3D Print Short Sleeve Unique Casual Flared Midi Dressvia

Slightly out-there dress

When you don’t want to blend in, have a bold dress that makes a statement. Go ahead and splurge on that awesome dress you’ve been eyeing. A little confidence is all you need to pull it off, and you’re guaranteed to get tons of compliments. Plus, if it doesn’t fit with any particular trends, it won’t look outdated. Before you get dressed, make sure you aren’t making any of these style mistakes that make you look old.

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Every product is independently selected by our editors. If you buy something through our links, we may earn an affiliate commission.

Marissa Laliberte
Marissa Laliberte-Simonian is a London-based associate editor with the global promotions team at WebMD’s and was previously a staff writer for Reader's Digest. Her work has also appeared in Business Insider, Parents magazine, CreakyJoints, and the Baltimore Sun. You can find her on Instagram @marissasimonian.

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