Tomboys no longer need to look like a marshmallow this winter as Tailored Tomboy’s Mary Houlihan offers quick strategies to spruce your winter wardrobe up. Read on…

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During the coldest months of the year, we tomboys can feel like a little like Randy from A Christmas Story. Now, if you aren’t familiar with the movie check out the visual below and you’ll know what I’m talking about:

Tomboy Style Fashion Tips Take Charge Of Your Tomboy Styled Winter Wardrobe Strategy Now Featured Tomboy Tarts

For us tomboys, the issue isn’t only trying not to look like a marshmallow, it’s also wanting to look stylish while feeling warm and comfortable.

Every year I get really excited about layering long before it’s necessary. When the leaves start to change and pumpkin spice lattes are on my mind, I cannot wait to wrap a scarf around my neck, even if it’s still hot enough to wear a t-shirt. But once the season takes that inevitable turn toward cold and darkness, I get so sick of putting on and peeling off the same layers I didn’t replace the year before, or the year before that.  Hindsight has taught me, you need more than one winter jacket, especially if you are fortunate enough to need it several months out of the year, and you need more than one scarf/mitten/hat option too!

January is the perfect month to evaluate what you are wearing all the time and take advantage of sales to prepare for the next year, you’ll thank yourself.  Here are some tips and tricks to keep in mind while evaluating your winter wardrobe and deciding what you will add to the mix.

SWEAT IT BY LAYERING IT

Tomboy Style Fashion Tips Take Charge Of Your Tomboy Styled Winter Wardrobe Strategy Now Featured Tomboy Tarts

When layering a sweater over a button down shirt, look for shirts that do not have a breast pocket. Most sweaters aren’t thick enough to disguise the outline of the breast pocket underneath, this is especially important for women with larger chests.

2 WINTER COATS ARE BETTER THAN JUST 1 IN THE FREEZING COLD

You should have at least 2 winter coats. One for dress and one for casual or one for day and one for night. Having two coats allows each coat rest time and increase the longevity of them both.  Check out my suggestions for day coats below from Topshop US.

Tomboy Style Fashion Tips Take Charge Of Your Tomboy Styled Winter Wardrobe Strategy Now Featured Tomboy Tarts

Winter coats are also definitely a splurge worthy item! Spend the extra money on the garment that everyone will see first, you will wear everyday, will keep you warm and you will have for years. Every winter you will pull that coat out of your closet and either thank yourself or kick yourself. Now check out some formal or nightwear coats for your tomboy winter closet.

Tomboy Style Fashion Tips Take Charge Of Your Tomboy Styled Winter Wardrobe Strategy Now Featured Tomboy Tarts

LEGGING IT

Tomboy Style Fashion Tips Take Charge Of Your Tomboy Styled Winter Wardrobe Strategy Now Featured Tomboy Tarts

Long underwear under pants – best to use long underwear that is tight like a legging. For you commuters out there, I am with you. I stand on that freezing cold platform and wait for the train and I give myself a big high-five when my legs aren’t freezing cold! Even if your pant of choice is skinny jeans, long underwear leggings will work, this is Tailored Tomboy tested and approved. A great brand for such long underwear or leggings is Cuddl Duds.

SOCK, SCARF AND HAT TALES

Tomboy Style Fashion Tips Take Charge Of Your Tomboy Styled Winter Wardrobe Strategy Now Featured Tomboy Tarts

Do not underestimate the warming power and style power of socks, scarves and hats. While the myth was debunked that we lose half our body heat through our head, I can personally testify that I feel 100% warmer when I’m wearing a hat. Plan these items around the shoes and coats you already own.

My recommended socks are by Smart Wool

These socks come in every shape, size and style. The knee highs socks work great under mid-calf boots, thick hiking socks fit perfectly under snow boots and ankle length casual socks work well with brogues.

DON’T FORGET PIECES FROM THE PAST

Use pieces from other seasons to create stylish and warm layers – get more cost per wear from each item in your closet by using them in multiple seasons. For example, put a muscle t-shirt under a flannel for casual football Sunday or layer lighter jackets under a sweater or a winter coat. I love the stuff that comes out of Instagrammer and fashion/travel blogger AlexCloset. Check out some winter styles below:

Tomboy Style Fashion Tips Take Charge Of Your Tomboy Styled Winter Wardrobe Strategy Now Featured Tomboy Tarts

Now that we are in full winter swing and spring inventory will soon be hitting the stores, take inventory of your winter wardrobe and take advantage of winter clothing on sale to ensure that next winter is your most stylish yet!

I’m Mary Houlihan for Tailored Tomboy and I’m a stylist specialising in tomboy style. Check out my official site for your tomboy style needs because you can’t have an adventure in high-heels!