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How to Dress for Winter: Stay Warm & Stylish During the Cold Months

How to Dress Warm for Winter

Braving the frigid winter cold is a feat on its own—but coming up with outfits that are both stylish and suitable for the weather? Now that’s a completely different game. Understanding how to dress for winter goes beyond tacking on a warm coat to your usual ensembles, it’s a balancing act marked by smart layering and piece-picking.

If staying warm while embracing your unique style is a top priority as the cold winter weather settles in, we’re here to give you the rundown on the many ways in which you can make your wardrobe work for you, even on the chilliest days. Whether wintertime means ice-frosted buildings and cloudy gray days or your regularly scheduled sunshine and slightly cooler temps, we’ve got your wardrobe woes covered.

How to Dress for Winter: The Style Essentials


How to Dress for Winter: 5 Top Tips for Staying Warm

  1. Make smart footwear choices
  2. Pair your skirts with tights
  3. Learn how to layer
  4. Wear the rainbow
  5. Accessorize for added warmth


How to Dress for Winter: The Style Essentials

If you’re like most women, your wardrobe is an ever-changing source of inspiration—lending itself to your particular tastes while keeping you looking fresh all year long. Wintertime’s chilly arrival calls for warm layers, heavy coats and a keen eye for tying everything together in a fashion that works for you and with you. 

With these four winter style wardrobe essentials, you’ll be well equipped with all of the garments you need for achieving your own personal version of wintertime chic. 

  1. Sweaters
On the left, model lying on floor wearing The Loafer in Fawn. On the right, close up of model leaning against a plant.

When it comes to dressing warm for the winter, a sweater serves as the perfect base layer to inspire the rest of your outfit. Though autumn may be the initial call for sweater weather, winter’s season’s greeting gives you valuable extra months of wearing your favorite cable knits, chenilles and fleeces. Appropriate for your work days and your lounge days, sweaters are the material embodiment of the warm and cozy feeling your body craves come wintertime.

Make it Yours: Necklines

Turtleneck: Characterized by an effortlessly sophisticated high-rolled collar that folds to fit snug under your chin, the turtleneck sweater is a winter wardrobe must-have.

Cowl: Loved for the natural draping shape it creates at the neckline, cowl neck sweaters add chic dimension and flirty flair to any cold weather ensemble.

Mock neck: Mock necks are faux-turtlenecks that feature a similar high-collar that does not fold down but looks just as sleek.

Crew: Keep it classic with a rounded crew neck sweater that sits comfortably around your neck and is easy to pair with all of your favorite warm layers.

  1. Shoes
Close up of model wearing The Chelsea in Fawn, stepping out from behind a screen with plants.

Understanding how to dress for winter starts from the ground up. Even if your shoes are the last piece to your outfit puzzle, they should never be an afterthought. Responsible for carrying you comfortably on your commute and keeping your toes warm, your shoes should be equal parts functional and fashionable. 

Make it Yours: Silhouettes

Round-toe: There’s no such thing as a bad time to break out your favorite pair of ballet flats. These low-profile shoes are always in style for a reason—they’re a no-brainer option for all of your wardrobe essential and statement pieces.

Chelsea boot: Get the high-coverage you need to brave the winter wonderland outside in a pair of ultra-cute Chelsea boots. Perfect for casual and classy events, the Chelsea boot is bound to be your go-to winter shoe.

Loafer: Take the things you love about your everyday ballet flat, but modernize it and increase the coverage. The result is a polished loafer flat that delivers the all-day wear you never knew you needed.

Slip-on sneaker: Slip-on sneakers are great for the woman on the hunt for a shoe that stands the test of time. Perfect for every season, these laceless shoes pair well with everything from jeans to sundresses.

  1. Outerwear
Two views of a model sitting on a stool wearing The Point in Fawn, against a translucent screen background with plants.

There’s no better feeling than finishing off your outfit for the day with a coat that truly brings your vision to life. Much like wrapping yourself inside of a warm blanket, the right coat can keep you feeling toasty from the moment you step out the door to the moment you return home. Experimenting with your outerwear is one of the easiest ways to add dimension, texture, and color to an outfit.


Make it Yours: Styles

Puffer: Puffer coats are back in a big way and these bulky synthetic down jackets are here to stay. Simple and chic while being sporty and casual, puffer coats pair well with just about anything you have in mind.

Anorak: Anorak coats are amazing full-body coats that cover you from the thigh up while maintaining a breathable loose-fit. Typically crafted with thick, waterproof materials, anoraks are the ultimate winter coats.

Chesterfield: Longline Chesterfield coats exude luxury and elegance while keeping you toasty all winter long. Featuring blazer-like lapels and a slim-fit silhouette, the Chesterfield is flattering on all body types.  

Cocoon: For those days where you’re feeling like a pea coat just won’t cut it, a cocoon jacket is a high-fashion alternative that adds a bit of jazz factor with its dropped shoulders and ballooned waistline. 

  1. Accessories

As the final touches to an outfit, the accessories tie everything together, creating a flawlessly fluid look that exudes confidence and style. Serving as the bold pops of color to a monochrome outfit and the functional pieces to keep your neck, hands and head warm, accessories are a truly elemental piece of any winter wardrobe. 

Scour your closet or favorite boutiques for these must-have winter accessories:

Jewelry: Necklaces, bracelets, rings and watches are all glamorous additions to both dressed-up and dressed-down looks. Adding dazzle factor has never been so gorgeous!

Hats: There’s no such thing as a bad hair day when you’ve got a warm and trusty hat to keep you looking polished and put together throughout your day. From beanies to fedoras and all other styles in between, the hat options are endless.

Sunglasses: Though the sun may set earlier, it still comes out to play and brighten your day. Shield your eyes while elevating your look with a posh pair of sunglasses.

Purses: Keeping your everyday essentials by your side is no small feat, but with a snazzy handbag in your hand or across your body, you can safeguard your phone, wallet and keys from the chill.

How to Dress for Winter: 5 Top Tips for Staying Warm

Tip #1: Make smart footwear choices.

Rifling through your wintertime wardrobe is a completely different experience when it comes to your footwear. Not only do you need to suit yourself up with a pair of shoes that can brave whatever weather befalls your city, but those shoes also need to match the same brilliant personality you outfit yourself with every day.  

Versatility is king—whether you’re headed to the office, catching up with your best friend, or packing up for a long-awaited vacation, your shoes should be sturdy and stylish enough to go where you go and keep you warm all the while.

Consider stocking up popular winter shoe styles:


Tip #2: Pair your skirts with tights.

Just because the weather is cold doesn’t mean you have to stash away your favorite skirts. Wear your leggy looks well into the wintertime by pairing your winter skirt outfits with tights. The thicker the tights, the warmer the wear. No need to battle out the cold when you’re perfectly (and fashionably) equipped with the accessories to make your wardrobe work.

Tip #3: Learn how to layer. 

Believe it or not, layering is far less complicated than you may initially think. While it may take a few bouts of trial and error to achieve the runway-ready look you’re after, having the right tricks up your sleeve will ensure you’re able to craft flawlessly layered looks every winter.

Follow this foolproof formula to ace your layering game :

  1.  Minimize your color families to one or two
  2.  Mix up your fabrics and textures
  3.  Experiment with proportions and hemline lengths
  4.  Stick to one bulky piece per outfit


Tip #4: Wear the rainbow. 

Though the weather may be gray, your outfits don’t have to follow suit. Spice up your days by complementing your usual neutrals with bold pops of color. Add a splash of personality to an all-black ensemble by donning a bright sapphire blue accent. Or add a focal point of interest to a cream and beige look by wearing an eye-catching pair of animal print flats on your feet.

However you decide to express your personal radiance, do so without any color boundaries. Forget tired color schemes, create and embrace your own.

Tip #5: Accessorize for added warmth. 

From scarves and beanies to gloves and shawls, there are so many winter accessories that are specifically designed to keep you toasty on even the most frosty days. Much like harnessing the art of layering, fine-tuning your eye for accessorizing simply takes a few rounds of experimentation. Whether you opt for a pair of faux-fur earmuffs or a pair of vegan leather mittens, your accessories serve as sleek finishing pieces to all of your winter looks.

There’s no right or wrong avenue to take on your journey toward learning how to dress for winter, so long as your wardrobe is well equipped with the right pieces. Warm clothes for winter can be just as quirky, bold, minimalist, or refined as the rest of your clothing collection—all it takes is a careful eye and confidence to create seamless outfits that feel as good (and warm) as they look.

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