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16 Classic Dresses Every Woman Should Own

Updated: May 29, 2024

These classic dresses are just what you need for every occasion—and you’ll wear them for years to come.

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classic dresses collagerd.com, via tobi.com, via target.com

Dresses that never go out of style

Whether or not you think of yourself as a “dress person,” you might like to have a few classic dresses in your life. They’ll be the ones you pull out of your closet time and again when you need a surefire hit for work, play, a special occasion, or just everyday casual wearing. And while they don’t need to cost a fortune (or even close to it), they are among the best investments you can make in your personal style because they provide an instant wardrobe upgrade.

“It’s important to have at least three dresses you can wear to life events,” explains Astar Davidson, a fashion merchandising and style expert. “The best classic dresses are trend-resistant and remain in style for years at a time, and they can be transformed with accessories to suit every major event life might throw at you.”

How we chose the best classic dresses

From LBDs and evening wear to T-shirt dresses and casual work dresses, each of these styles will make you look and feel like the timeless beauty you are. To find the best of the best, we consulted style experts, scoured online user reviews, and also found brand-new pieces with design features we absolutely adore. Just make sure to grab the right shapewear, your best bra, and your favorite sandals, boots, or pumps to complete each look.

Joanna Black Dress
Via Mmlafleur.com Via Mmlafleur.com

Best little black dress

M.M. LaFleur The Joanna Dress

“A classic black dress will serve you endlessly and be your go-to for parties, dinners out, and both happy and somber events,” says Davidson. “If you can only choose one item to add to your closet right now, make it a little black dress.”

This curve-hugging M.M. LaFleur dress is an excellent choice for pear-shaped bodies, offers a modest long sleeve and square neckline, and hits just around the knee. You’ll love wearing this flattering number everywhere that requires a little pizzazz. Pro tip: The right handbag can help you adjust the look of this LBD depending on where you’re going.


  • Flatters a variety of body shapes
  • Modest design that enhances and honors feminine curves
  • Machine washable and wrinkle resistant
  • Available in sizes 0 through 16
Tartan Ruffle Tiered Dress
Via Vineyardvines.com Via Vineyardvines.com

Best holiday dress

Vineyard Vines Tartan Ruffle Tiered Dress

Whether you have dozens of holiday parties to head to each year or you just like to get a little extra festive come fall and winter, Davidson suggests having one versatile little red dress in your arsenal. “You’ll wear this throughout the cold-weather months,” she says. “It’s appropriate for Thanksgiving, the entire Christmas season, and the holiday parties that surround that time of year, and then you’ll break it out again around Valentine’s Day. A classic style that is less focused on trends and more focused on quality will last you for years to come.”

This preppy Vineyard Vines frock is just the ticket. Its super soft, silky fabric flatters thanks to an included lining, and the ruffled sleeves will add a flirty flair to your holiday look. Plus, it works on a variety of sizes and body types. If you want to feel fancy at home, try these house dresses that are stylish and comfy.


  • Fun, preppy style that’s ideal for the holiday season
  • Available in sizes 00 to 24
  • Feminine ruffled detailing
Sundown Dress
Via Greybandit.com Via Greybandit.com

Best slip dress

Grey Bandit Sundown Dress

A slip-style dress is a classic that you’ll definitely keep in rotation. It layers like a dream, is lightweight, and won’t add bulk to your body or your closet. You can wear it on its own for a glammed-up night out or layered over a fitted white baby tee for a vintage 1990s throwback look that still holds up today. Or throw one of your best sweaters over it for an updated look that hits current trend notes.

This Grey Bandit Sundown dress comes in a versatile midi length and is offered in a neutral-toned print that will stand the test of time.


  • Midi length
  • Easy to layer
  • Transitions from day to night
Floral Smock Waist Dress
via whitehouseblackmarket.com via whitehouseblackmarket.com

Best maxi dress

White House Black Market Smocked Maxi Dress

You’ll wear this flirty, figure-flattering floral maxi from day to night and through at least three seasons of the year, thanks to its breezy, flowy material that offers just a hint of skin without showing too much. The smocked waist offers a belted effect that cinches, narrows, and tucks so you present an hourglass shape every time. It’s available in sizes 00 through 20 and regular and petite silhouettes to serve several body types, too. Choose from this list of affordable jewelry to complete the look.


  • Versatile wearing
  • Available in regular and petite sizes 00 through 20
  • Smocked waist that offers comfortable cinching
Smock Waist Pleated Midi Dress
Via Whitehouseblackmarket.com Via Whitehouseblackmarket.com

Best summer dress

White House Black Market Smocked Waist Pleated Midi Dress

There’s nothing more summery than a crisp white dress with a neatly cinched waistline. This one from White House Black Market features a flattering mock neck that offers the illusion of a halter style (but with far more support), smocking at the waist that offers an hourglass silhouette, elegant pleating, and an airy sleeveless cut. Even better, this classic dress gives you timeless Hollywood-bombshell vibes when you wear it. Summer also calls for sun hats, so while you’re shopping, make sure to pick up a few that are specially suited for your various seasonal styles and activities.


  • Affordable
  • Fully lined
  • Available in regular and petite sizes
Skater Dress
Via Torrid.com Via Torrid.com

Best casual dress for curvy bodies

Torrid Skater Dress

This affordable dress offers a flattering shape that instantly creates an hourglass silhouette on frames up to size 6X. Its magic-producing features? A ruched V-neck, a subtly defined high waist, and a flowy bottom that doesn’t create extra bulk. It’s an affordable, washable frock that can be worn over leggings, tights, or on its own, and it can be easily dressed up or down with accessories and makeup. It’s also a great choice for business casual days.


  • Inclusive sizing, from regular size medium through plus size 6X
  • Affordable price point
  • Easy maintenance
For All Occasions In Silk Cami Dress
Via Lilysilk.com Via Lilysilk.com

Best A-shape dress

Lilysilk For All Occasions in Silk Cami Dress

Of all the classic dresses out there, the A-shape style might be the most timeless of them all. This silk take on that always-popular silhouette is one you’ll wear over and over again because of its figure-flattering drape that hits just below the knee on most body types. The all-natural, premium materials make the ordinary shape feel ultra-luxe and like a kiss from the clouds against the skin. It really is that soft, and it’s the ideal piece for those who can’t stand the idea of itchy materials.

“If you want a casual warm-weather look, wear this cami dress over a plain white baby tee and pair it with some tennis shoes,” says Davidson. “Or dress it up with sparkly jewelry, sophisticated heels, and a wrap or coat for a holiday party in the winter.”


  • Comes in seven rich neutral shades
  • Modest price point
  • Available in sizes XS through XXL
Embroidered Linen Dress
Via Bodenusa.com Via Bodenusa.com

Best vacation dress

Boden Embroidered Linen Dress

The comfort of this slightly-above-the-knee dress will make it your go-to vacation piece. You can even pop it over your favorite swimsuit when heading out to lunch. It’s a fuss-free embroidered linen beauty that is surprisingly machine washable, offers a relaxed fit that lets you truly enjoy life, and gathers slightly at the front to give the skirt movement. The concealed side zipper and seam pockets offer practicality and high-end detailing that are hard to find at such an affordable price point.


  • High-end details like a side zipper and seam pockets
  • Machine washable
  • Available in sizes 0 through 22
  • 3/4 sleeves
Maxi denim Shirt Dress
Via Belladahl.com Via Belladahl.com

Best denim dress

Bella Dahl Maxi Shirt Dress

Take chambray to the next level with this denim-feeling maxi shirt dress you can wear in all seasons. “Chambray is a lighter material with a denim look that offers timeless casual wearing,” Davidson explains. As for how to pull off this look? “Don’t go overboard with the denim-on-denim looks like an early-2000s pop star,” she says. “Think about wearing a look like this one with summery wedge sandals, tennis shoes, or booties, depending on the weather.”

You can machine wash it, layer it with other pieces, and make the most of buttoned chest pockets. More pockets equal more fun, right? You’ll also love the high-end details and marks of excellent craftsmanship on this dress, including roll-tab buttoned sleeves and a sassy side-slit detail with frayed hemming. Plus, it’s even comfier than your favorite pair of jeans.


  • Easy maintenance and washing
  • 100 percent TENCEL fabric
  • High-end detailing
  • Year-round wear
American Giant Hoodie Dress
Via American-Giant.com Via American-Giant.com

Best sweatshirt-style dress

American Giant Hoodie Dress

Add this hoodie dress to your wardrobe immediately if you love soft snuggles and casual frocks. You’ll wear it on its own at home or layered over your favorite fleece-lined leggings when you’re running errands. It’s a sporty, athletic-inspired take on classic dresses that will quickly become your go-to piece. Chances are, you’ll love it so much, you’ll want it in each of the four available neutral colors.


  • Comfortable, cozy sweatshirt material
  • Hooded
  • Easy machine washing
  • Available in sizes XS to XL
2 In 1 Nursing Maternity midi dress
Via Kindredbravely.com Via Kindredbravely.com

Best maternity dress

Kindred Bravely 2-in-1 Nursing & Maternity Knit Midi Dress

It’s hard to find stylish maternity dresses that transition to nursing wear (and give you the time and space to make that transition). But this Kindred Bravely dress does both in style, and it’s offered at an affordable price point under $90. It’s a two-piece dress that can be worn year-round and features detachable elements that make growing and nursing a breeze. The ribbed fabric feels like a lightweight sweater, and it comes in two neutral shades, camel and black, so you’re set for several years (or babies) to come.


  • Available in sizes S through XXL
  • Fits growing (and shrinking) bumps and offers easy nursing access
  • Neutral colors
  • Modest price point
Ruched Side Sleeveless Dress
Via Nordstrom.com Via Nordstrom.com

Best sleeveless dress

Treasure & Bond Ruched Side Sleeveless Dress

Did you know that this casual dress is one of Nordstrom’s best-selling items? Well, it is, and it’s not hard to see why: It’s under $50, and it comes in a dozen colors ranging from neutral to seasonal. Plus, the flattering side ruching makes it a go-to classic dress for women who love to layer their looks. You can wear it solo with a pair of platform heels if you’re going out, or Davidson recommends pairing it with solid-colored trainers and a cropped denim jacket for a daytime look. It’s up to you, but with so many positive reviews and such an affordable price point, you may want to scoop it up a few colors. Before you check out, you might also want to nab Nordstrom’s best shapewear for this dress and every other.


  • Under $50
  • Easy to dress up or down for most occasions
  • Flattering ruching
Come Around Off Shoulder Sweater Dress
Via Tobi.com Via Tobi.com

Best modern sweater dress

Tobi Come Around Off-the-Shoulder Midi Dress

If your take on classic dresses has to have a slightly modern, up-to-date spin, this oatmeal-colored Tobi dress is for you. It’s a holiday dress when you want it to be, a dinner-out-with-friends frock when the mood strikes, or a sophisticated date dress, thanks to its off-the-shoulder bardot neckline and sassy side slit. Pair it with booties, belt it if you feel inclined, or add colorful accessories to give it your own spin. Just make sure you have a comfortable and supportive strapless bra to go under it.


  • Exposed shoulders without showing too much skin
  • Modern midi length
  • Cozy sweater material
  • Neutral, on-trend color that won’t go out of style
Rogue gown
Via Azazie.com Via Azazie.com

Best floor-length dress

Azazie Rogue Gown

You’re going to reach for this floor-length dress time and time again. It’s a trend-resistant gown you’ll wear to black-tie affairs, weddings, galas, and more. The best part? It is super affordable for a piece like this (around $100), comes in an extended size range, and is offered in literally dozens of shades ranging from classic black to soft, summery peach. It also makes a smart bridesmaid choice since it’s so adaptable, flattering, and within most budgets.


  • Narrow bodice
  • Available in dozens of colors
  • Extended size range
  • Budget-friendly
Elegant Split Flare Formal Evening Gown
Via Amazon.com Via Amazon.com

Best statement dress

MAYFASEY Split-Sleeve Dress

“It’s important to have at least a few modest picks in your wardrobe,” says Davidson. “Modest doesn’t have to mean frumpy, though—you can use added fabrics and longer hemlines as an excuse to play with silhouettes and unusual draping. Add sex appeal with a strappy heel or boot instead.” This classic cape-style dress borrows trends from the 1980s and ’90s and comes in nine exciting colors that are sure to please even the pickiest shoppers. It’s a flattering, non-revealing piece offered at an affordable price that has garnered thousands of Amazon reviews.

“The fabric is much nicer than I’d thought it would be and has lots of give and stretch,” writes one verified Amazon purchaser. “This makes me feel elegant and has all the coverage I want. I love it so much, I plan to order it in other colors.”


  • Under $50
  • Multiple color offerings
  • A sexy, updated take on modest dressing
Summer Plus Size Flare Dress
Via Amazon.com Via Amazon.com

Best fit-and-flare dress

Nemidor Plus Flare Dress

Every now and then, a plus-size dress comes along that is so universally flattering and easy to care for that it sells out. And then it sells out again. That’s exactly the case with this Nemidor fit-and-flare midi dress, and reviewers are saying they’re buying it in as many colors as possible because it’s a “must-have.” This cult favorite comes in nearly 40 colors and prints, as well as in sizes 14 to 26, and it’s so budget-friendly at under $30 that you’ll want to add a few to your cart.

“Very cute dress! It is very soft and has pockets, so that alone makes it great,” writes verified Amazon reviewer Lindsay. “It is a perfect length for work, and the neckline is modest as well. It does not cling too badly, so it is flattering.”


  • Under $30
  • Available in sizes 14 through 26
  • Dozens of colors and prints
  • Pockets