How To Take Your Wardrobe From Tomboy To Woman And Still Be Comfortable

Are you a jeans and t-shirt kind of girl? And are you still wearing the same t-shirts from five years ago? Welcome to the club.

By Paula Gallagher2 min read
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I like to be comfortable. I was never one to suffer for fashion…which also meant my fashion suffered. I lived in jeans, t-shirts, and sneakers – and not particularly flattering ones at that. It wasn’t until I was a young adult that I saw the light about colors, silhouettes, and coordinating shoes.

So, if you’re still dressing the same way you did as a tomboy teenager, then let me whisper some hard-won words of fashion wisdom in your ear: You can dress like a classy, feminine woman without sacrificing your comfort!

If you’re ready to upgrade your image from tomboy to woman, then come with me.

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Learn What Flatters You

Before you buy a single new item, you first need to figure out what colors are flattering for your skin tone and hair. We have several articles on different methods for this here and here. A few other ways you can figure out what colors to wear is by noticing which colors get you compliments (a light blue sweater my MIL gave me never failed to get me a comment on how it brought out my eyes) or by asking a friend to help you. 

Next, figure out your body type, and research what silhouettes are recommended for your particular type. We have articles on that here and here. For example, bootcut jeans are much more flattering on me than mom jeans, but I’m still wearing jeans!

Upgrade with a Nicer Version

Swapping out what you already love and wear with a classier version is the easiest way to upgrade your whole wardrobe. Swap that graphic tee for a solid color v-neck tee with a feminine cut or a pretty blouse. Swap jeans for chinos or wide-leg trousers. Swap sweatshirts and hoodies for classy sweaters. Swap running shoes for all white sneakers. Swap…you get the point. 

Choose Natural Materials

Dressing like a woman often requires paying a bit more and investing in good-quality pieces. Aim for items crafted from natural fabrics like silk, wool, cotton, linen, cashmere, and leather. Not only do they look and feel nicer than cheap rayon and polyester, but they will also last much, much longer with the correct care.

Accentuate Your Waistline

I don’t know about you, but a lot of the tomboys I knew wore extra baggy t-shirts to hide their feminine curves. Now that we’re grown up, it’s time to let those curves shine! So go ahead and tuck your shirt into your high-waisted jeans, wear a belt to highlight your waist, and master the French tuck for looser blouses or sweaters. 

Balance Your Proportions

Part 2 of accentuating your waistline is thinking about proportions. If you want to wear a baggy sweater, then pair it with slim-line pants. If you want to wear wide-leg jeans, then pair it with a tight-fitting top. This will keep your figure from being swallowed by the looser item.

This balancing act applies to patterns as well. If you’re wearing a patterned top, then wear solid color pants. If you’re wearing a floral skirt, then keep it solid on top. Some people may feel ready to pattern mix like Blair Waldorf or Emily Cooper, but personally, I’m not one of them!

Matching Sets

If putting together coordinating outfits is where you scratch your head and shrug, then let me draw your attention to matching sets. These come in everything from loungewear to skirts and blouses to tank tops and pants. Easy to put together and easy to wear? Sign me up!

Buy More Shoes

The days of wearing the same pair of sneakers with everything are behind you. Ahead are the days of comfortable but coordinating shoes! Invest in white sneakers for the summer and black or leather sneakers for the winter. Get a pair of black boots and a pair of brown ones. Buy a pair of white sandals and a leather pair. Find a casual shoe like loafers or mules you like. You can wear all of these shoes with jeans or shorts, but they all look nicer than your running shoes. Coordinating your shoes with your top or your belt is an easy way to level up your outfit without sacrificing comfort. 

Closing Thoughts

If fashion sense doesn’t come naturally to you, you’re not alone! For some of us, it’s a knowledge gleaned over years of reading about it, analyzing other people’s outfits, and experimenting with our own! But once we get, we get it.

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