These classic dresses will become your go-to for every occasion. They’re timeless, fashionable, and you’ll be able to wear them for years to come. Every editorial product is independently selected, though we may be compensated or receive an affiliate commission if you buy something through our links. Ratings and prices are accurate and items are in stock as of time of publication.
Dresses that never go out of style
Having a few classic dresses in your closet is always a good idea, even if you don’t consider yourself a “dress person.” They’ll be the ones you reach for time and again when you need a foolproof outfit for work, play, a special occasion, or just everyday casual wear. And while they don’t need to be expensive (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 versatile dresses you can wear to various life events,” explains Astar Davidson, a fashion merchandising and style expert. “The best classic dresses are trend-resistant and remain in style for years, so you won’t have to keep up with the latest fashion trends. They can also be transformed with accessories to suit every major event life might throw at you.”
How we chose the best classic dresses
Looking for a versatile, timeless dress that will make you look and feel beautiful? We’ve got you covered. We consulted style experts and scoured online user reviews to find the best of the best in LBDs, evening wear, T-shirt dresses, and casual work dresses. We 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.
Best little black dress: M.M. LaFleur The Joanna Dress
“A little black dress is a timeless piece that will 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. It 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.
Our flattering and modest designs enhance and honor feminine curves, while being machine washable and wrinkle resistant. Our sizes range from 0 through 16, making it easy to find the perfect fit for any body type.
Best holiday dress: Vineyard Vines Tartan Ruffle Tiered Dress
If you celebrate several holidays throughout the year or you just enjoy getting dressed up for the fall and winter months, Davidson recommends having a versatile little red dress in your wardrobe. “You can wear this dress for Thanksgiving, all throughout the Christmas season, and for any holiday parties you might attend,” she says. “And then you can 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.”
Get that holiday party look with this preppy frock from Vineyard Vines! The super soft, silky fabric is flattering and the ruffled sleeves add a touch of flirtiness. The dress works for a variety of sizes and body types. And if you want to feel fancy at home, try one of these stylish and comfortable house dresses.
This dress is the perfect holiday piece with its feminine ruffled detailing and preppy style. It’s available in sizes 00 to 24, so no matter your size, you can rock this look for all your holiday parties!
Best casual dress: Maurices 24/7 Pocket Boyfriend Midi Dress
You’ll want to live in this boyfriend midi dress from Maurices 24/7 – it’s that comfortable! The easy-to-wear knit fabric and functional pockets make it a great choice for lazy days at home, running errands, or even dressing up with leggings, a cardigan, and boots. Plus, the affordable price means you can buy more than one!
This garment is under $35, has functional pockets, and is machine washable. It is available in sizes XS through XXL.
Best everyday dress: Athleta Balance Dress
The Athleta Balance dress is one of Davidson’s favorites for a reason – it’s available in two neutral colors, has long sleeves, and comes in sizes XXS through 3X. Plus, it’s offered in petite and tall sizes, meaning it’s designed to flatter almost every body type. And if that wasn’t enough, this “everything dress” also has two side pockets and a hidden arm pocket for mini essentials. No wonder it has hundreds of positive reviews from happy customers!
Looking for a light and airy fabric to keep you cool in the summer heat? Our French terry material is perfect for hot days! Plus, it’s machine washable for easy care. This fabric is also a great choice for plus-size and curvy body types.
Best slip dress: Grey Bandit Sundown Dress
A slip-style dress is a versatile piece that you’ll want to keep in your wardrobe rotation. It’s easy to layer and can be dressed up or down. You can wear it on its own for a night out or layer it over a fitted white tee for a vintage-inspired look. 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.
Our midi length dress is perfect for layering or wearing on its own! The easy to wear silhouette makes this piece a versatile must-have for your wardrobe. You can effortlessly take this look from day to night with a change of accessories.
Best maxi dress: White House Black Market Smocked Maxi Dress
This figure-flattering floral maxi is perfect for any occasion, 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.
Our versatile smocked-waist dress can be worn as a casual day dress or dressed up for a more formal occasion. It’s available in regular and petite sizes 00-20 and features a comfortable, cinching waist.
Best summer dress: White House Black Market Smocked Waist Pleated Midi Dress
Nothing says summer quite like a well-fitted white dress that shows off your curves. This one from White House Black Market comes with a mock neckline that gives the illusion of a halter dress (but with more support), smocking at the waist for an hourglass shape, elegant pleating, and a sleeveless cut that keeps you feeling cool and comfortable all day long. Not to mention, this classic dress will have you feeling like a Hollywood bombshell all summer long. And since summer also calls for sun hats, pick up a few different styles to suit all of your various seasonal activities.
Our women’s clothing is not only affordable, but also high-quality and fashionable. We have a wide range of sizes so that every woman can find something that fits her perfectly, and we have both regular and petite sizes available.
Best casual dress for curvy bodies: Torrid Skater Dress
This affordable dress is perfect for creating an hourglass silhouette on any body type up to size 6X. Its magic-producing features include 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.
Our sizes range from regular size medium to plus size 6X, so everyone can find their perfect fit. Our affordable prices make it easy to keep your wardrobe up-to-date, without breaking the bank. And easy care instructions make it simple to keep your clothes looking their best.
Best A-shape dress: Lilysilk For All Occasions in Silk Cami Dress
If you’re looking for a classic timeless dress, the A-shape silhouette is one of the most popular and flattering styles out there. This silk version of the A-shape dress is figure-flattering and hits just below the knee, making it a great option for many different body types. The all-natural, premium materials make the dress ultra-luxe and incredibly soft, making it a great option for those who are sensitive to itchy materials.
The A-shape dress silhouette is one of the most popular and timeless styles for a reason – its flattering drape and below-the-knee length makes it a versatile option for many body types. This particular A-shape dress is made with all-natural, premium silk materials that make it ultra-luxe and ultra-soft, perfect for those who can’t stand the idea of itchy materials. You’ll want to wear this dress over and over again because of its figure-flattering silhouette and luxurious feel.
Looking for quality plus-size clothing that won’t break the bank? Look no further than our collection of seven rich neutral shades, available in sizes XS through XXL. With a modest price point, you can build a versatile wardrobe that will take you from the office to the weekend with ease.
Best vacation dress: Boden Embroidered Linen Dress
This slightly-above-the-knee dress is so comfortable, you’ll want to wear it on every vacation. It’s easy to throw on over your swimsuit when you’re heading out to lunch. The embroidered linen is machine washable and has a relaxed fit that lets you truly enjoy life. The gathered skirt has a concealed side zipper and seam pockets for high-end detailing at an affordable price point.
Our women’s tunic top comes with high-end details like a side zipper and seam pockets, and it’s machine washable for easy care. It’s available in sizes 0 through 22, and it has 3/4 sleeves for a flattering look.