If there’s one throwback trend that has staying power, it’s the slip dress. The lingerie-inspired shift left the confines of the boudoir decades ago when ‘90s style icons like SATC’s Carrie Bradshaw (who could forget the infamous naked dress?), Clueless’s Cher Horowitz (in white Calvin Klein), and of course Kate Moss (that sheer metallic slip she wore to a party in 1993 was truly iconic) made sleepwear-as-streetwear a mainstream thing. With the recent resurgence of all things 1990s, the slip dress has been revived in all its silky, slinky glory — it hardly even feels like a trend anymore.
“Aside from the ‘90s still being a big influence, the fall collections were filled with ‘20s style slip dresses to fit the ‘roaring ‘20s’ vibe we are in right now,” Los Angeles-based stylist Catlin Myers tells TZR. “On a more practical but related note, I think people are wavering between wanting comfort but also wanting to dress up as they go out again. Slip dresses accomplish both things — [they’re] comfortable enough to sleep in, but also polished enough for a night out look,” she says. The versatile wardrobe mainstay can be dressed up or down, for daytime or date night, and while you might not think of it as a seasonal staple, with a quick refresher on how to wear a silk slip dress in winter, you'll see that it's in fact a solid cold-weather choice.
It’s all about layers, layers, and more layers. Whether you’re wearing it over a fitted long-sleeved top, under a chunky turtleneck or cardigan, with jeans or tights, or topped with a leather jacket or overcoat, the key to your winter slip dress outfit is to pile on other pieces until peak coziness is reached. While this may not be the most minimalist approach to the typically-simple staple, it allows for a huge range of styling options, from feminine and glam to trendy, sporty, or grunge. Plus, perhaps most importantly, you’ll be warm.
Continue below to discover 14 inspired ideas for how to style a slip dress in the winter.
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Over A Textured Turtleneck
Myers suggests slipping your dress over a turtleneck — but not just your regular fuzzy sweater. “[Try] a turtleneck with an interesting texture like fishnet, mesh, or lace,” she tells TZR. This is the perfect combo for those winter days that aren’t too overbearingly cold.
With An Oversized Blazer
For a tonal look, Myers recommends pairing a structured blazer and a waist belt in darker or lighter colors than your dress. The layers keep you warm while adding interest and dimension to your winter slip dress outfit. You can also use the belt-and-blazer idea as an easy way to color block.
Pair With Gloves
“Fall 2021 showed a lot of opera gloves,” Myers tells TZR. “Either a cashmere or leather opera glove is a good way to add extra warmth and make a statement for a more formal event,” she says, recommending a slip dress, sweater vest, and leather glove combo, “either tonal or color blocking à la Valentino.”
Under A Slouchy Sweater
“A slouchy sweater keeps it casual and cozy,” Myers tells TZR. “With a knee-high boot, it becomes a timeless cold-weather look.” An oversized turtleneck will eliminate the need for a scarf and lend some much-needed warmth to the look while creating a chic contrast against the silky slip sticking out below.
Over Straight-Leg Jeans
If ever there was a time to give the dress-with-pants trend a try, this is your opportunity — especially if early 2000s fashion is your thing. There’s something effortless about wearing a slinky printed shift over a fitted black turtleneck and jeans, as though you were already fully dressed and ready to go and then threw on the slip dress at the last minute.
Layered To The Max
No frosty gust of wind is going to bother you when your ensemble is five layers thick. Arm yourself against even the most bitter chill with this outfit formula: black skinny jeans, cozy turtleneck, long-sleeve knit, slip dress, and wool coat. And since we’re focusing on comfort to an indulgent degree here, why not go ahead and wear sneakers while you’re at it?
Over A Button-Down Shirt
Layer a crisp oxford shirt under a more bohemian-style slip dress for a fashion-forward mix of classic and cool. According to Myers, this look is “a great way to make a slip dress feel more professional or covered without hiding it under a jacket.” It all comes back to that rule of layers.
With Doubled-Up Jackets
For a luxe, lounge-y vibe, style a basic black slip dress under two lighter-weight robe jackets. A patterned kimono is the perfect base layer to add some texture and detail. Then complete the look by topping it off with a bold-colored longline duster.
With A Leather Jacket
A substantial leather jacket is just the thing a floaty, pastel gown needs to be wearable during winter. A black jacket in a slightly oversized fit gives the frothy frock a tough edge. For even more contrast, finish with super-opaque black tights and white heels.
With A Hoodie And Puffer
Hey there, athleisure fanatic, here’s a look to suit your streetwear-loving soul. Start with a lace-trimmed slip dress (make sure the lace is at the hem, so it isn’t hidden by the layers up top). Then pull on your coziest, slouchiest hoodie and a puffer coat for an outfit that’s as comfy as it is cool-girl approved. The paparazzi will be all over you.
Over A Velvet Top
Nothing winterizes a look faster than a touch of velvet. “It’s the perfect combo to stay warm with a luxe feel,” Myers tells TZR. “Try an interesting jewel tone or unique sleeve to really make it feel special.” A flocked top in that deep jewel tone is perfect for the evening when your go-to black slip dress just doesn’t cut it alone.
With Suiting Separates
You could just wear a blazer over your silk slip dress, but if you’re looking for something a bit more interesting, go one step further with the menswear motif and add tailored trousers underneath. A slightly flared or wide-leg style will extend the leg-line, and the combination of several long-line layers feels elegant and luxurious. Go for plain gray or match your pants to a plaid or houndstooth jacket.
With A Shearling Coat
Embrace your inner ‘90s grunge girl with this iconic combo. Rock a retro floral frock, bulky shearling coat, and black combat boots. It’s an outfit that young Drew Barrymore definitely would’ve worn.
In Head-To-Toe Black
Wearing all black is often the default when dressing for winter, but incorporating a mix of textures and layers keeps a monochrome ensemble from ever looking boring. To a mid-length black slip, add a long knit cardigan and a wool bomber jacket (bonus style points for a version with some contrast detailing) on top, and blackout tights and sock boots on bottom. The more layers, the better — just make them all black.
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