Winter is upon us, and with it comes the promise of cozy nights by the fire, snow-covered landscapes, and festive gatherings. But winter can also be a fashion challenge. How do you stay warm and comfortable without sacrificing style?

Introducing the Cozy Chic Winter Challenge! This fun challenge is designed to help you embrace the beauty of winter while expressing your personal style through stylish and comfortable looks.

Each day, for the next week, step into your closet with one goal in mind: to create the cutest cozy looks imaginable! Ditch the sweatpants and sweatshirts and let’s have some fun with winter colors and textures. This is a completely go-on-your-own, DIY Challenge, so read on to hear some tips for upleveling your style this winter!

When you think of winter, what images come to mind? Most likely you think of crisp and cool settings such as snow-topped trees, the red and green that appear around Christmas, or the icy blues you see in the daytime sky. Take these images as inspiration when you are creating your looks.

The first thing you want to do is decide on your FOCAL PIECE. Will this be a colorful sweater, a jacket or cardigan, or a dress? It makes it so much easier to choose what you are working around and build from there. The key is to make sure that your focal piece is not something you will be removing. For this reason, cute as they are, hats and gloves are not a great focal piece. Here are a few ideas to get your brainstorm going:

  • Turtleneck in a pattern
  • Pullover sweater in a color
  • Jacket with some texture
  • Top with some shine
  • Long Cardigan with a fun pattern

Next, think about LAYERS. There is no more perfect time to layer up than winter. Layers give your outfit dimension and I recommend them year-round, but the perfect time to wear them is during the colder months. You can give an element of contrast to your look by playing with color here or, if you prefer, you can complement your look by playing in the same color family. Depending on what your Focal Piece was, you may re-engineer the layers and think about your under piece instead (if your focal piece was a jacket or cardigan for example).


Consider Balance. The one thing you DON’T want to do, a commonly made mistake, is to add too much volume all over your body. Because winter fabrics and knits are heavier in weight than during the rest of the year, you want to make sure you are balancing your outfit. If you are wearing a wide-leg pant, for example, you want to keep what you wear on top more fitted. If you are wearing a bulkier sweater up-top, keeping to more of a straight-leg jean or a legging on the bottom is going to be better.

Add some texture. During the winter months, you can play with so much texture because the fabrics of winter are all about texture! Think about different weaves on your knits, or faux-fur, or metallics (which add visual texture). If you are dressing for a party, sequins are fab! What about pairing a satin skirt with a cropped chunky knit sweater? Play with this.

Have fun with accessories. During the winter months, there are so many fun accessories to play with. You can pop your outfit with a chunky scarf or a blanket scarf. You can play with hats of all kinds in the winter. Gloves add an extra dose of fun (and warmth!) in the winter. Go ham here! Shoes fit into this category, too. There are so many fun shoes to play with in the winter. Think: Chelsea Boots, Lug-sole Loafers, Combat Boots, Ankle Boots, Knee Length Boots, Mid-Calf Boots.

Don’t forget about your coat. Imagine visiting a highly rated, expensive restaurant. The chef takes the time to add the perfect spices, cook the meal to the perfect temperature, drizzles the top of the dish and plate with a fabulous sauce and then sends the plate out covered in plastic wrap. It completely throws off the vibe AND how the meal tastes. Visual presentation is everything. The hard truth is that most of the time, your outerwear is all anyone will see of your outfit, so take time here. Invest in a beautiful coat that allows you to show off your personality. I honestly believe that having an outerwear wardrobe that translates the fashions that you typically wear is key. For example: a puffer coat for your more athleisure looks, a pea coat to take things up a notch, a trench for classic year-round style. I could honestly write an entire blog about coats. Don’t look over this step!

It’s easy to get into a routine and dress without imagination during the winter, going only for dark fabrics, dark coats, and becoming one with the sea of black walking down the street. I encourage you to have fun this winter and make getting dressed each morning a chic experience!

Make sure you snag my FREEBIE with Bonus Tips on Stylish Winter Dressing. It will be easy to print and keep as inspiration in your closet! Grab it here.

Tag me with your Cozy Chic Looks on Instagram @michelleglassstyling and use #MGSCozyChicWinterLooks. I can’t wait to see what new looks you create!

Stylishly Yours,


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