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Dear CF,

I've been dressing like a tomboy for as long as I remember. My wardrobe is essentially white, gray, and black, with variations of jeans, t-shirts, flannel shirts, and Converse. Since starting university though, I realized that I actually like colorful, girly looks, that dresses and skirts flatter my figure better than jeans, and that my preference for tomboyish clothes stems from lack of confidence.

How can I start to change my look without making a huge jump from one style to another? I think a soft gamine look would reflect both my usual simple look and the look I'd like to have and bridge the two, but it's really difficult to even start looking for pieces to add to my wardrobe!

Thanks!

Love from New Zealand

Our Response

As someone who grew up with two older brothers, I fully understand living the tomboy life, but I've never been one to limit myself to one specific style of dress. While I love my Converse and baby-soft tees, I'm also a huge fan of breezy sundresses and girly heels. 

It can be hard to transition your wardrobe from one style to another, but the key is to gradually add pieces to your existing closet that reflect the style you're aiming for. Definitely keep what you already have. It sounds like you've got a really good foundation of basics to work with.

Start looking for other items like skater skirts, a little black dress, pastel blouses, a white button-down, ballet flats, and colorful shorts— basically anything that you like and that you find "girly." Pieces like these are feminine, but can easily be paired with the "tomboy" basics you already own. 

Don't forget accessories, either! A string of pearls, a simple charm bracelet, or a bow can go a long way in transforming an outfit. 

I've created three outfits below to give you a little inspiration on how to add feminine touches to simple, more "tomboy" looks. 

Outfit #1

Product Information: T-Shirt, Flannel, Skirt, Converse, Bow, Earrings, Bag 

If you're still hesitant about branching out of your comfort zone, this outfit is perfect for you. You most likely already have the white tee, flannel shirt, and sneakers in your closet at home! Throw on a skater skirt for that feminine touch, and you're good to go. 

Outfit #2

Product Information: Jeans, Top, Sneakers, Bag, Sunglasses, Headband, Ring 

Just because you want to change up your style doesn't mean you have to toss aside your favorite pair of jeans. Instead of throwing on a plain tee, opt for something a little more feminine. This ruffled, floral crop top looks so cute paired with white Converse, a messy bun, and a vintage-style headband. 

Outfit #3

Product Information: Blouse, Shorts, Sandals, Sunglasses, Rings

This outfit is the most feminine of the three with its dainty gold accents and retro flair, but the structured blouse and shorts still have that tomboy touch. If you're really open to making a change in your style, I would definitely recommend an ensemble similar to this one. 

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What do you think?

What are some of your tips for transitioning your style from one to the other? Do you think your style is more feminine or "tomboy"? Would you wear any of these looks? Let us know in the comments!