How to Look Stylish in Cold Weather

How to look stylish in cold weather

Thankfully, we’re not there yet… But I bet most of you are already asking the question how can I look stylish in cold weather? Winter weather is just around the corner. You’d think a Midwesterner would welcome the cold. However, every November I seem to ask myself why I haven’t moved to Florida! That said, family roots run deep… I’ve never left the Midwest. In fact, as a Wisconsin-native (who spent 10+ years attempting to look stylish while reporting out in the elements – think lots of sub-zero temperatures), I have picked up a few tips and tricks for those wondering how to look stylish in cold weather.

The looks I’m sharing are November-focused. However, the strategies we’ll talk about can carry you deep into winter.

Your number one goal? Adding warmth without adding bulk!

how to stay stylish in cold weatherhow to stay stylish in cold weatherCoat | Boots | Jeans

How to look stylish in cold weather

1. Look for coats/cozy layers that DEFINE your waist

The first rule of looking chic in cooler weather? Don’t loose your shape under all those extra layers! At 4’11, this has been especially imperative for me. Oversized fashion just doesn’t work for short gals. However, this principle isn’t limited to petites. When you begin adding bulky layers, you need to find ways to maintain your body proportions.

A small nip in the waistline—in the form of a coat/sweater with a tie waist or belt—works wonders. It’s universally flattering and keeps your jacket from overwhelming you! Styles that taper in ever-so-slightly at the waist can also serve this role. Even if you don’t typically like highlighting your waist, I would encourage you to experiment with belted outerwear. You might be pleasantly surprised by the way a simple tie reduces the “bulk” factor with coats while adding shape in all the right places!

My plaid coat is an example of that. It’s a really warm piece that allows you to rock your feminine curves while staying toasty. It’s one of Chicwish’s best-selling and comes in a variety of patterns, plus solid colors. I like it so much, I actually ordered it in two color varieties! (And you might just recognize a certain someone on the brand’s home page right now if you scroll down a bit) Here are a few other elegant, waist-defining options…

When you are coat shopping, aim for the highest wool content you can get within your price range—above 50 percent is pretty good. It’s nearly impossible to find 100 percent wool without spending a fortune. This coat has a 65 wool percentage. Steer clear of coats that are primarily polyester. They won’t stand up in cold weather.

how to stay stylish in cold weather

Boots | Sweater | Faux Leather Skirt

2. Invest in a quality boot wardrobe

Once November rolls around, you will rarely find me without boots on—either knee high or over-the-knee. Why? Boots offer significantly more warmth than pants, particularly if you wear fleece lined tights with wool socks over the top (Smartwool is a popular brand). They cut the wind effectively and leave your legs protected, even on the coldest of days. In fact, I often buy my boots a half size up to accommodate that additional layering. When my TV station would send to cover stories on bitterly cold Wisconsin days, I’d layer two pairs of tights. On the most awful days, I would tuck a handwarmer in the toe.

Read this next: News Anchor Outfits – The Best Amazon Dresses

The other reason I love boots is because they create such an elegant look. Consequently, I love pairing boots with skirts and dresses, even in the dead of winter. You just need the proper layers underneath! It’s still relatively warm here, so I don’t have my tights on just yet in these shots. But they are definitely on standby!

I’ve purchased both cheap boots and higher quality pieces, but now trend toward the latter. While I love sharing fashion bargains with you guys, you get what you pay for when it comes to boots! Therefore, I do splurge in this area. Winter coats, boots, and jeans are always smart fashion areas to invest in because these are pieces you will wear again and again.

Dress | Boots | Belt | Clutch (similar)

A few well-respected brands to check out:

  • Stuart Weitzman – The gold standard for OTK boots. Still too pricey for me, but the next time I see an amazing sale, I might spring for them.
  • Sam Edelman –  My favorite brand. Really comfortable and super high quality.
  • Vince Camuto – I’ve always had great luck with this brand. Opt for a style with a pointed toe to create the appearance of a longer leg line.

how to stay stylish in cold weather

3. Pay Attention to Your Base Layers

Chunky and thick does not necessarily equate to warm! If you’re trying to figure out how to look stylish in cold weather, you need to begin with a great base layer (or two depending on the weather). These should be made of natural fibers (e.g. Merino Wool) and thin/fitted, so they can trap air close to your body.

For instance, this coat is a lighter weight 60 percent wool blend, suitable for 60-40 degree weather. However, with great base layers, I was able to wear it comfortably on days that were significantly colder than that. Bottom line: You don’t need to confine your use of base layers to the ski slopes! They’re great under everyday or office attire too.

I should mention that when I’m talking about base layers, I am not talking about your grandparents’ bulky long underwear. Modern versions, such as this affordable set from Amazon, are sleek enough to wear under almost anything. If you are in the “always cold” crowd like me, layering up will make you feel so much better. It will also allow you to additional mileage out of clothing you don’t necessarily want to cover with a puffer coat!

how to stay stylish during cold weather

4. Keep that Neck Warm! Embrace Turtlenecks & Cowls

I have a serious love affair with turtlenecks. Not only are they classically elegant, but also very functional. When the temperature drops, they do a great job of keeping a usually exposed area of our bodies under wraps. Do yourself a favor and make sure you have a simple black and creamy neutral turtleneck in your wardrobe. They will look great as layering pieces under coats and sweaters, but can also stand all on their own with jeans on those warmer days!

When it comes to warm/cozy knits, I highly recommend this tan sweater (also in gray). It’s a thick, heavy 100 percent acrylic knit and really keeps the heat in. The length is ideal for leggings!

Sweater | Jeans | Bag

Quick note about this lovely cream sweater: It’s listed as a sweater dress. However, it runs really short. I’d call it a tunic length top. Unless you’re under 5′, you’ll want to pair it with jeans and leggings. When I wear it as a dress, I like to add black tights and an ankle bootie. 

What are your cold weather styling tricks? Would love to add to this list!


  1. Suvojit Roy | 15th Nov 20

    Your article is really very informative and attractive too. I like the way you describe each and everything. Keep sharing these kinds of article.

  2. S Mishra | 15th Nov 20

    Such a beautiful and classic bag!

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