Day or Night, You’ll Live in These 3 Easy Dresses All Winter

Versatility at its finest.

Day 3 - Street Style - LFW FW15
Melodie JengGetty Images

There’s very little satisfaction in buying a piece of clothing that you wear once and then find yourself stumped when you try to figure out other ways to style it. It ends up tucked away in a drawer or closet, forgotten and replaced with pieces that are much easier to wear. The three dresses below are strong examples of the latter.

With classic silhouettes and neutral colors, these styles aren’t just sleek and simplistic—they’re also the perfect first step to creating endless winter outfits. Day to night, work to weekend (and even weddings!), all it takes is a bit of creative zhuzhing to transform each dress to fit whatever occasion you need.

Below, take a closer look at two different outfit ideas—one casual for day, and one more dressed-up for night—based around three of our favorite dresses. Trust us: You’ll want these within arm’s reach at all times.

1. The Sheath Dress


Clothing, Outerwear, Brown, Sleeve, Suit, Jacket, Formal wear, Beige, Blazer,
Shop the look: Calvin Klein coat and dress, Shashi barrette, Mango bag, Gal Meets Glam x Margaux flats

A simple sheath dress is perhaps the easiest go-to work look. And with the addition of a few thoughtful details—a printed flat, a textured bag, or a subtle hair accessory—it instantly feels much more exciting than your typical office-style fare.


Clothing, Black, Dress, Little black dress, Footwear, Sleeve, Shoulder, Joint, Day dress, Cocktail dress,
Shop the look: Calvin Klein dress, BaubleBar earrings, Black & Brown belt, Loeffler Randall clutch, Prada shoes

Since a sheath silhouette is pretty traditional, use playful pieces to dress it up for a night out. A killer pump, chain link belt, and a small dose of feathers should do the trick.

2. The Printed Dress


Clothing, White, Black, Sleeve, Footwear, Jeans, Shirt, Fashion, Design, Outerwear,
Shop the look: Calvin Klein jacket and dress, Maria Black earrings, & Other Stories bag, ByFar boots

A sleek, flat boot and denim jacket keep this look casual and comfortable. It’s ideal for a daytime date, brunch plans, or weekend museum hopping.


White, Black, Footwear, Clothing, Product, Fashion, Shoe, Black-and-white, Font, Dress,
Shop the look: Calvin Klein dress, Wolf Circus earrings, Ben Amun bracelet, Urban Outfitters bag, Iro boots

Lean into heavy metal details to take this dress from Saturday afternoon strolls in your favorite neighborhood to Saturday night sets at your favorite local music venue. Choose footwear with a sturdier heel in case dancing is on the agenda.

3. The A-Line Dress


Clothing, Black, Blue, Dress, Sleeve, Footwear, Uniform, Neck, Day dress, Little black dress,
Shop the look: Calvin Klein dress, Roxanne Assoulin bracelet, Charles and Keith bag, Colours Co Shop socks, Dr. Martens shoes

Dress down a classic A-line LBD with polished and chunky Dr. Martens loafers. Add a hands-free crossbody bag and sweet details such as a ruffled sock and colorful, stackable jewelry.


Clothing, Black, Dress, Little black dress, Day dress, Footwear, Sleeve, Formal wear, Cocktail dress, Shoe,
Shop the look: Calvin Klein dress, Zara headband, Mejuri earrings, Shiraleah bag, Sarah Flint heels

A touch of luxe texture—crystals! fringe! metallics!—make this a simple black dress ready for any cocktail-attire affair.

This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses. You may be able to find more information about this and similar content at
Advertisement - Continue Reading Below
More From Fashion