20 Cute Outfits That Will Up Your Tomboy Game

Experimenting with these unique and preppy tomboy looks is so much fun.

By Pratima AtiPratima Ati  • 

Tomboy outfits exude an androgynous vibe that is ruling the street style world. Unlike popular misconceptions, wearing tomboy outfits is not about your sexual orientation or being nonchalant about fashion. It is about expressing yourself by playing with masculine silhouettes and staying away from conventional feminine attires. From Kendall Jenner and Coco Rocha to Priyanka Chopra – women are embracing the tomboy look like never before. This post brings you the most fashion-forward and fun tomboy outfit ideas. Swipe up!

Tomboy outfits gained popularity in the late 19th and early 20th centuries as a symbol of the suffragette movement and feminism.

How Do You Dress Like A Tomboy?

The tomboy look is an inherent style that resonates with some people more than others. Whether it is your default setting or a style you want to try, the idea is to bring together pieces that reflect this personality.

Add accessories that are bold, rusty, or robust as opposed to dainty, delicate, and featherlight.

Leather, denim, and bomber jackets. Distressed denim. Boyfriend or mom jeans. Oversized hoodies or sweaters. Turtle necks. Sneakers. Converse shoes. Combat or ankle-length boots. Pantsuits. Big blazers. Flannels. Overalls. Beanies. Bandanas. Baseball hats. These are your staples, but feel free to add more and play around in a way that reflects your bold and badass self.

20 Cute Tomboy Outfits

1. Boy Shorts

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The borrowed-it-from-the-boys kind of look exudes the tomboy vibe like nothing else. A pair of athleisure boy shorts, a half-tucked linen shirt, and sneakers is how you paint the town red in the summer.

2. Overalls

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Are you a fan of camo and suspenders? Sport them both to nail that tomboy look. An Iron-Maiden T-shirt to go with the overalls, a half bun, Converse shoes, and hoops can do the job just right.

3. Frayed Shorts

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Invest in a pair of rugged or frayed shorts. Put your hair up in a bun and throw on a pair of white Superstars or Airmax sneakers!

4. Oversized Shirt And Jacket

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Shirt dresses – I mean the really long and oversized shirts that are worn as dresses – are really in and fit the tomboy bill perfectly. Top it up with a puffy jacket and boots for good measure.

5. Leather Trousers

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Raise the hotness quotient with a pair of leather pants, a tank top, and black sneakers like a boss lady. Add aviators or any sunglasses of your choice to finish off the look.

6. Skinny Jeans With Denim Shirt

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Swing into the feminine side just a little bit with this outfit. Jeans are a signature tomboy attire. Spruce them up a little with white boots and a denim shirt. Smokey eye makeup is your way to go for this look.

7. Bold Monochromes

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Welcome corduroy into your closet to build a bold monochrome outfit without moving away from the theme. Combats, Converse sneakers, or Oxfords sit well with this look.

8. Flannels

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Tomboys swear by flannel or plaid. Tie one at the waist, layer it, or go for an oversized one, and you are sorted.

9. Pantsuit

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Pantsuits are bulldozing their way into runways, fashion houses, and clothing lines. Talk about exciting and fun outfits!

10. Leather Jacket

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Leather jackets never fly under the radar when it comes to tomboy-ish looks, and they are here to stay.

11. Oversized Blazer

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Reign as a street style superstar in this consumingly oversized blazer, straight cut jeans, and a high bun!

Did You Know?
The rolled-up jeans and sailor jerseys with French stripes, which was synonymous with the tomboy style, was popularized by Jean Seberg, a renowned American actress.

12. Bomber Jacket

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Want to put in zero effort but still look like you did? Then, a bomber jacket is your bae! Cropped boyfriends jeans, a tank top, ankle boots, a bomber jacket, and a high bun is how you turn the story around.

13. Side Stripe Pants

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All things with a side stripe are having a moment right now, and they are inherently tomboy-ish. Tracks, trousers, or jeans. If you don’t want to go all the way out with this look, add a trench coat.

14. Business Casuals

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Too cool for school? Can’t wrap your head around formal dressing? Then, try this instead! It hovers around the idea of formal dressing with its boxed silhouette, but does not give in completely.

15. Shorts And Crop Top

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Tomboy meets townie halfway with this look! A tube top with a dark wash denim jacket and jeans, a belt, and laceless combat boots is how you own this look.

16. Tutu Skirt Or Dress

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I know a tutu skirt is the opposite of tomboy. However, even if you detest the idea of anything feminine, you can still try this outfit. It is subtle with its tomboy vibe but still fits the bill.

17. Distressed Denim

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Were you wondering why this didn’t make it further up in the list? We just didn’t want to state the obvious. Distressed denim, hoodies, and combat boots are straight up everyday essentials.

18. Hoodie Dress

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If there’s one thing I learned from this dainty diva, it is to nail the tomboy attire subtly. She lives in hoodie dresses and so can you if you are willing to explore the other side of fashion.

19. Boyfriend Shirt

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Raid your partner’s closet a bit and yank his blue shirt out. Pair it with mom or bootcut jeans to make it your own.

20. One-Piece Dress

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Homecoming or prom just around the corner? I’m assuming the tomboy in you cannot begin to accept the typical girly attire. Borrow a one-piece dress from a friend or rent it out, throw on your leather jacket, and finish it off with boots just the way you like it.

Infographic: 8 Outfit Ideas To Effortlessly Dress Like A Tomboy

The world of street style is dominated by the androgynous vibe that tomboy attire emanates.
A trendy tomboy look emphasizes effortless pieces that are easy to wear. So, open yourself to new styles and experiment with typically masculine silhouettes. Check out the infographic below to find inspiration for your next tomboy outfit!

8 outfit ideas to effortlessly dress like a tomboy (infographic)

Illustration: StyleCraze Design Team

Save the high-quality PDF version on your device now.

Download Infographic in PDF version Download Infographic
Download Infographic in PDF version

Tomboy outfits are all about the androgynous vibe and playing with masculine silhouettes. It is a common misconception that tomboy looks can’t be fashionable. If frayed jean shorts with crop tops, monochrome outfits, oversized blazers, and leather pants don’t scream street style, what does! While the term ‘tomboy’ refers to a natural personality trait, we can all play with androgynous outfits by adopting the norms of a true tomboy or changing them to meet our own. Fashion is all about self-expression, being comfortable in your skin, and having fun, so don’t be afraid to play with it.

Frequently Asked Questions

What does tomboy stand for?

A tomboy is a girl who behaves and dresses in a boyish manner and does not wear dresses too often.

Can tomboys wear makeup?

Most girls considered to be tomboys don’t wear much makeup apart from lip balm and eyeliner.

What can a tomboy wear to prom?

The key to being a tomboy is wearing what makes you feel comfortable rather than dressing up for others. Pick something formal that you like: it can be a vintage dress, a custom dress, or a cool pantsuit. You can wear these for formal events like homecoming, prom, etc.

Do tomboys wear ponytails?

Yes, tomboys often sport ponytails and braids as they are easy hairstyles and keep hair off their face.

Key Takeaways

  • Tomboy outfits are about expressing yourself by playing with masculine silhouettes and staying away from conventional feminine attires.
  • You can rule the tomboy look by adding boy shorts, oversized hoodies, and sneakers to reflect your bold and badass vibe.
  • The idea is to play around with different styles and tweak them to reflect your personality.
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