5 Timeless Dresses Every Woman Should Own

  • Copy by: Jess Keys

Building a wardrobe can be overwhelming, especially when trying to find the perfect balance between trendy pieces and classic staples. So while we all know most trends come and go, there are a handful of classic dress silhouettes that never go out of style!

To round up our favorite timeless dresses, we teamed up with the ladies of Brass who know a thing or two about classic frocks. Whether you’re heading to a meeting, going out with the girls, or leaving for vacation, these five will never let you down.



DRESS IT UP: Add statement gold pumps and a killer necklace
DRESS IT DOWN: Slip-onsjean jacket, and a neck scarf

The classic sleeveless fit and flare dress: It’s an any season, any occasion number that you’ll pull out of your closet again and again. Flattering on nearly every body type, it has a fitted waist and a flared skirt. Wear it to an interview, date, meeting, church, or even a wedding. There’s not much this little dress won’t get you through so we recommend investing in both black and navy. (You’ll thank us later, we promise.)



DRESS IT UP: red party pumpsgold statement earringsdark red lip
DRESS IT DOWN: Lace-up ballet flats and a timeless trench 

Modest, yet sophisticated, the A-line dress withstands the test of time—it never goes out of style and it’s perfect for any woman, at any age. We love the rich navy hue of this version, which is universally flattering on any skin tone!



DRESS IT UP: for work, layer over a crisp button-down, black embellished pumpstightsearrings
DRESS IT DOWN: with white sneakersblanket scarf

A staple for fall and winter when the weather gets chilly, the sweater dress is your best layering bet! Wear it with tights or a button down layered underneath (or both!).

Top it off with a vest, scarf, blazer, or jacket—however you please! It’s the perfect length for work, but can be easily dressed down for a cozy Sunday brunch. (You catch our drift—it’s versatile, to say the least.)



DRESS IT UP: over-the-knee bootsred lipstatement necklace
DRESS IT DOWN: flat ankle bootieschunky cardigan

Another magical number that works for all seasons: the shirt dress! (A slightly more polished version of its cousin, the t-shirt dress! More on that below.) While this frock works for all casual to mid-dressy occasions, where it really shines is travel. 

Wear it with gladiator sandals, sneakers, ballet flats, riding boots, or high heels—anything you have in your suitcase, really. The long sleeves come in extra handy when visiting religious sites with dress codes (like cathedrals) when traveling. On the flip side, you can roll them up if you’re warm and the shorter length will keep you cool. (Or, if it’s chilly, pull on some tights and you’re good to go!)

This version is made of polyester, which is extremely durable and wrinkle resistant. Just pull out of your suitcase and you’re off!



DRESS IT UP: wear to work with a blazersharp flatsgo-anywhere tote 
DRESS IT DOWN: Keds and a chambray shirt tied at the waist 

Last, but certainly not least, the most casual of them all: the t-shirt dress. Wear it to Saturday lunch with the girls, to the beach, on the plane, a daytime date, or even to work with a blazer! It’ll keep you cool and comfy all year long. (And since pajamas aren’t acceptable in public, this frock is a pretty close second.)

Which style is your favorite? How do you style your go-to frock?


This post was sponsored by Brass but all of the opinions within are those of The Everygirl editorial board.