How to Not Look Boring This Winter

It’s been getting colder and colder in Chicago. Still, no snow on the ground (not that I really want it) but the temperatures are dropping, which means it’s winter coat season. Now if you’re like me and not a millionaire that can afford like 10 winter coats you typically have just one… I’ve been wearing the same red coat that I got from ModCloth YEARS ago. My wardrobe also gets darker and darker as the days also get darker and darker. I find myself in the same 3 sweaters with the same pair of pants, typically my yoga pants… Not only is my wardrobe pretty monochrome but I noticed while riding the train in the morning or on my way home from work that not only is my wardrobe a mix of brown, black and gray but so is everyone else’s. So instead of falling into the monotony of the season, you can really dress up your closet with a few simple updates.

Loud Winter Accessories

Since we spend a lot of time bundled up this time of year our outfits can oftentimes take a backseat to our outerwear. We can fall into the cycle of purchasing a very basic winter coat so it is versatile and will last more than one season. Let’s face it, those suckers are expensive! So instead of hopping on the latest color trend in your coat options try adding a pop of color with your winter accessories. I love a cute pair of mittens or hat with a bright bobble or I’ve noticed the beret trend is alive and well in winter 2019, and in my opinion, it is so chic. So throw in a neon pink pop or a cherry red which is also a festive color. This will also allow you to switch things up next year and make you feel like you have a brand new coat.

Bold Jewelry & Handbags

Like hats, gloves, and scarves the way to dress up your winter look is through accessories. Even with an all-black look, which is honestly my go-to winter wardrobe throwing on a pair of large hoops, or fun bold earring can help elevate any look. Along with your jewelry, you can throw on a bright bag to add a pop of color to your winter outfit.

Play with Colors

As I’ve been saying this whole time playing with colors is a great way to add a bit of cheer to the dreary weather and your monochrome outfit. Adding those pops in accessories is great but don’t be afraid of throwing some color into your clothes, wear some summer dresses under your winter sweaters, and wear bright tights with your sweater dresses. Be bold and try something new in your wardrobe.


Obviously, layering is the best way to stay warm when it’s 30 degrees outside. Throw a comfy sweater over a slip dress, or a long sleeve shirt under your favorite sleeveless dress. Get use out of your favorite spring and fall dresses by using basic layers.

Mix Textures and Patterns

Don’t be afraid of wearing florals, and patterns this season as well, pull out those maxi skirts and dresses, pair them with bodysuits and other textures for a fun take on your typical winter wear. I love adding houndstooth and darker florals to my wardrobe in the winter. Pair an organza top with a wool skirt and tights to play with new textures.

Don’t Be Afraid of Oversized

This tip is, especially for my petite ladies. Though I think everyone should embrace oversized in the winter, often times petite ladies can find themselves swimming in winter garb, to begin with. But I say lean into it. Wear those oversized scarves wrapped around your face or that oversized sweater as a dress with a pair of tights and combat boots. Don’t be afraid of rolling sleeves or even belting sweaters to create shape.


Finally, if these tips aren’t enough and you want to try a cape coat or even a brighter colored jacket use companies like Rent the Runway to give you an opportunity to try them out without the commitment to the hefty price tag.

Renting, accessories, and layers and textures. I love giving my winter wardrobe a little refresh without breaking the bank. How do you dress up your winter closet when it’s feeling kind of boring?


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