Ask CF: How Can I Add a Feminine Flair to My Tomboy Style?

Want to switch up your style, but don’t know where to start? CF is here to help!

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Tomboy style

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!

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!


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.

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

tomboy meets girly style

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.

Related reading: The Ultimate Guide to Tomboy Outfits for Girls

Outfit #2

laid-back feminine look

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

white button-up, red shorts, slide-on sandals

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.

Do you have a pressing fashion question? Ask away!

Is there a piece in your closet that you never know how to style? Do you have an important event coming up? Is there a certain trend that is completely lost on you?

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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! 

1 thought on “Ask CF: How Can I Add a Feminine Flair to My Tomboy Style?”

  1. I like these looks but what seems to be a huge factor in making them more feminine is the hairstyles. I wonder what the reader who has a short bob can do to girly up her look since a messy bun is out of the question.


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