Welcome to the latest edition of Ask CF! Every two weeks, we select a reader fashion question and answer it here on the site. Do you have a specific fashion question for us? Scroll to the bottom of this post to learn how to send it our way!

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Ask CF Question

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.

{RELATED POST: The Ultimate Feminine Capsule Wardrobe}

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.