9 Clothes And Accessories For Tomboys Who Love To Play Dress-Up

A lot of people associate being a tomboy with playing with the boys on the yard, avoiding girly clothes, and not caring about looking pretty. At least, that was the association tomboys had when I was a little kid. There’s also an idea that tomboys ultimately grow out of all of this and continue on to their ultra gendered destiny of mascara and dresses and blah blah blah. Okay, I’m going to ignore the ridiculous gender politics for a second and say, sure, whatever. But when it comes to style, while some tomboy types definitely trade in their grass stained pant for a mini skirt, plenty more still like rocking more masculine style clothing. They’re just a little more age appropriate.

But if your style leans more tomboy and if you’re going to an event that isn’t super casual, the struggle is real when it comes to finding something that’s appropriate and matches your personal style. A friend of mine was a tomboy as a kid and sill claims to be one today, and she has such a hard time finding cute items to wear when she wants to be a little bit dressed up–for a date, a party, an interview, etc. If you find yourself in the same boat, get some inspiration from these ninclothes and accessories for tomboys who love to play dress up.

Faux Leather Moto Jacket

You can literally throw this leather jacket on top of anything with a nice pair of shoes and make it look like you spent a long time trying to look chic. Faux or not, a nice-looking leather jacket can be magical.

Buy it at Forever 21 for $25

Grid Print Blouse And Gaucho Set

Rock a wide leg pants and a cute top to match with this grid print gaucho set. This would look cute with a nice pair of ankle boots or some shiny loafers,

Buy it at Forever 21 for $44

Daisy Street Wrap Front Playsuit

Uh, plenty of tomboys love the color pink! What's great about this playsuit is that with a pair of nice shoes and cute accessories this can look really dressed up. But you can wear it on the basketball court and it won't look out of place with a pair of your favorite sneakers.

Buy it at ASOS for $14

ASOS Curve Dungaree Jumpsuit In Jersey

Wear this on top of your dressiest blouse, wear some cute boots, and you're good to go. You can even wear your favorite hat with it and still look chic.

Buy it at ASOS for $50.16

ASOS Reclaimed Vintage Co-Ord Check Set

If you're into wearing long skirts you're going to absolutely adore this set. This outfit will look great with your favorite sneakers. Top it off with a black baseball cap and you're golden.

Buy it at ASOS for $17.19

ASOS Thea Mid-rise Girlfriend Jeans In Majesty Blue Wash

Yes, you can totally dress up mom jeans. Just wear a shirt that's a little more dressy and pair with some ankle boots or cute oxfords.

Buy it at ASOS for $31.35

Foxiedox Canary Dress

Show off some skin without showing off too much skin for your comfort. This dress is a really nice balance!

Buy it at Nasty Gal for $58

Layered Varsity Stripe Rop

Get back to your sporty roots with this varsity stripe top. It's oversized enough to look really cute with a pair of leggings or skinny jeans.

Buy it at Forever 21 for $15.90

Mean Business Suspender Pants

Let everyone know that you mean business with the suspender pants. Pair with a crop top, or a nice blouse, or a turtleneck. No matter what, you're going to look pretty badass.

Buy it at Nasty Gal for $62


Are you a tomboy? What’s your personal style like? Tell us in the comments!

You can follow the author, Ashley Reese, on Twitter or Instagram. Don’t worry, she doesn’t bite!


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