3 Things I Make Sure to Do to Win the Winter Style Game

3 Things to Do to Look Good in the Winter

3 Things to Do to Win at Winter Style

Brr, it’s getting chilly, but that doesn’t mean that style has to suck! There are different factors to navigate in the winter compared to other seasons when it comes to style, which makes winter style trickier. For instance, you need to make sure your clothes keep you warm, that your footwear is practical for whatever the weather throws at you, and that you have the right pants to go with the shoes! (Pants and shoes can be a struggle, can’t they?) Winter weather presents real obstacles to feeling good in your clothes, but with a little forethought, you can make it so that winter style isn’t a complete drag.

As I always tell you, to make style easier, you need to start with the right pieces. Style is like a puzzle, and if you don’t have the pieces that fit together properly, it will be really hard to complete that puzzle—i.e., make outfits and get dressed easily. This is even truer with the obstacles that winter presents!

During the winter, there are a few things I focus on to make sure that I have the right puzzle pieces to stay warm (and stylish). Today I’m sharing with you some tidbits so that you can think more strategically about your wardrobe and make getting dressed in the winter a much smoother process.

SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.


1. Wear Underneath Layers

Layers to Wear Underneath Winter Outfits: black heattech layer + black and white striped long sleeve tee + skinny jeans + white leather earrings

If you have not yet read my post “How I Stay Warm in the Winter (While Trying to Look Cute),” take a moment to read that! If you’ve already read it, you know that I’m big on wearing a thin layer underneath all my outfits, namely HEATTECH layering tees from UNIQLO.

HEATTECH is a very thin layer that is soft, smooth, and stretchy, and never loses shape. It is formfitting without squeezing you (unless you get the wrong size), so that you can have an additional layer without bulk. The sleeves are intentionally a little short so that the layer stays hidden under your shirts or sweaters. I also get the scoop neckline to stay hidden under open neck tops. They come in several colors, but I just have black and beige (a few of each). For sizing, I’m usually size 6 or S/M and get these in M. Find them HERE.

I wear one every day in the winter, under everything.

I find wearing a HEATTECH layer helpful for a couple of reasons. First, it keeps you warmer, period. Second, it allows me to wear long sleeve tees and blouses that typically might feel too thin or not keep me warm enough, even if paired with a cardigan. Having this extra layer of insulation makes more of my tops wearable options in the winter, which means you get to use more of your closet for more of the year.


2. Have Layers You Can Wear Over Sweaters & Sweatshirts

Layers to Wear On Top of Sweaters and Sweatshirts in Winter: black and white long sleeve tee + green sweater blazer + black slacks + cognac booties + gold pendant necklace + brown top + brown and white sherpa fleece geometric print Kohl's jacket zip up + medium skinny blue jeans + taupe sneaker booties + tan leather tote bag + gold short initial pendant necklace

This one might seem random and perhaps dumb, but it’s very helpful to pay attention to! Make sure you have a couple of (STYLISH!) outer layer options that can be layered over sweaters and sweatshirts.

Typically, when you wear t-shirts, shirts, and blouses, it’s easy to throw on a cardigan as a comfortable default layer. But, cardigans don’t pair well with sweaters and sweatshirts. So, make sure you have options that you can layer on top of them that aren’t necessarily coats.

For workwear, blazers are one great option that you can layer over sweaters while still looking professional. In particular, I like the J.Crew Factory sweater blazers as options that are a little warmer (and softer and more comfortable), but any blazer will do.

For super casual outfits, especially ones that work well with really casual cozy boots or sneakers, I like sherpa or fleece zip-ups. They’re soft, warm, cozy, and comfy, and you can comfortably wear them indoors in super casual settings. I recommend having a couple of stylish options in your wardrobe that you can easily throw on top of sweaters or sweatshirts. (Keyword: STYLISH!) These work well in casual outfits with jeans and in athleisure outfits with leggings, so they are definitely worth having in your wardrobe.

Another option that goes well over sweaters and sweatshirts is a vest. Obviously, it will just keep your core warm as it’s missing the sleeves, but it’s still a notable layering option over sweaters and sweatshirts. For casual options that work with jeans or leggings, try this one from Target or this sherpa vest from Kohl’s (plus sizes HERE). For more polished casual looks or work settings, go for ones this quilted vest from J.Crew Factory.

I’ll include a roundup of blazers, sherpa and fleece zip-ups, and vests in the widget below. Whichever options you choose, just make sure you have a few layers that you can wear over sweaters and sweatshirts for casual outfits and/or work outfits! Then, whenever you feel like you need an additional layer (that is not a coat), you will have what you need.

Layers to Wear Over Sweaters & Sweatshirts – Casual and Work


3. Start With Your Shoes and Cuts of Pants FIRST!

Shoes to Wear with Straight Leg Jeans Different Boots and shaft lengths to go under pants

Ironically, I did not start the post with this, rather I saved it for last. 😆 Oh, well!

Whether you’re building an outfit or building a wardrobe, many people start with the top and then build the outfit or wardrobe around that.

However, one big element to my outfit and wardrobe strategies is that I usually start with the BOTTOM portion.

This is for a number of reasons which I won’t get into here, as the reasons are many.

But during the winter, the weather really dictates what you can wear more than in any other season. In particular, it dictates your footwear, as you could face pouring rain, snow, or just temps that bare ankles will not tolerate, and you need to choose shoes accordingly.

Then, your shoe choice dictates which pants you can wear. Which pants will actually work with the types of shoes I need to wear today? Important questions!

So, I always build from the bottom up, especially in the winter.

What handful of shoes will you wear this season?
As you are taking stock of your winter clothes and planning what wardrobe holes you have for the season, think through things like: What handful of shoes will you wear this season? When it rains? When it snows? When it’s cold but not raining or snowing? For running errands? For work? Quickly list the different types of weather or scenarios you might experience regularly this season, and then list the types of footwear you’ll need for them.

Which types of pants work best with those shoes?
Then, which cuts of pants work best with those handful of shoes? Do skinny jeans work, and will you want to wear them this season? Would you rather wear straight leg or bootcut pants, and do they work with your shoes? If not, what shoe options *will* work with those cuts of pants? And so on.

Those are really crucial questions to explore so that you have what you need on any given day no matter what the weather throws at you. Meaning, you have the right shoes, and you have a good selection of pants that work with those shoes. Like I’ve said, style is a puzzle, and you need the right puzzle pieces. These questions help you build a wardrobe full of clothes that fit together so that you have what you need. Make sense?

For help pairing shoes with different cuts of pants, check out “How to Wear Booties With Different Cuts of Jeans.”

I hope these things enable you to get dressed more smoothly and more confidently this season!

Also, if you want to be walked through questions like these each season to create your best and most easy-to-use wardrobe, and if you want to have a space to ask follow-up questions and go deeper and troubleshoot your personal style obstacles, join the PMT Style Club when it opens on January 10th!

previous post
next post