20 Cute Outfits That Will Up Your Tomboy Game

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

Reviewed by Michelle Wagman, Fashion Stylist Michelle Wagman Michelle WagmanFashion Stylist facebook_icontwitter_iconlinkedin_iconinsta_icon
Written by , MSc Pratima Ati MSc
Edited by , MA (English) Subhrojyoti Mukherjee MA (English) Experience: 4 years
Fact-checked by , MA (English & Literature), Certified Style & Image Consultant Srijita De MA (English & Literature), Certified Style & Image Consultant Experience: 2 years

Tomboy outfits exude an androgynous vibe that is ruling the street style world. Unlike popular misconceptions, wearing tomboy outfits or following gender-neutral fashion is not about your sexual orientation or being nonchalant about fashion. It is about expressing yourself by playing with masculine outfits, genderqueer clothing, or non-binary fashion 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!

Ace The Look
  • Footwear: Converse high tops are the most common choice for tomboy fits as they look great with overalls and distressed jeans.
  • Outerwear: You can keep a few classic pieces of outerwear in your wardrobe that can be styled with all tomboy outfits, like a bomber jacket, a flannel shacket, and an oversized coat.
  • Makeup: Opt for a no- makeup makeup look with tinted moisturizer and subtle lip gloss to highlight the simplicity of the outfits.
  • Hairstyles: Hairstyles like a messy lob, wolf cut, and pixie cut work best with tomboy outfits.

What Does Tomboy Mean?

In simple terms, tomboy refers to young women who have masculine traits and are more inclined to activities that are stereotypically associated with boys and men. They may also dress up in what is traditionally considered men’s clothing and project a more masculine body language.

In the 16th century, it meant a wild, energetic, boisterous, immodest, or rude female. Over the centuries, it has come to denote women who have an androgynous sense of style. However, in the 21st century, some people have come to call the term sexist. Regardless, the trope continues to feature in pop culture and art. When a woman has a charming masculine personality that heterosexual feminine women find attractive, those uncomfortable with the term sometimes refer to it as a “girl crush” personality.

How Do You Dress Like A Tomboy?

The tomboy look is an inherent unisex 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, turtlenecks, sneakers, Converse shoes, combat or ankle-length boots, pantsuits, oversized blazers, flannels, overalls, beanies, bandanas, baseball hats – the are endless tomboy outfits for girls to try! These are your staples, but feel free to add more and play around in a way that reflects your bold and badass self.

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

20 Cute Tomboy Outfits

1. Boy Shorts

Black boy shorts for tomboys
Image: Gettyimages

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

Printed overall with black tank top for tomboys
Image: Gettyimages

Are you a fan of camo and suspenders? Sport them both to nail that gender-neutral style. 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

Frayed shorts for tomboys
Image: Gettyimages

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

Oversized printed shirt and black quilted jacket for tomboys
Image: Gettyimages

Shirt dresses – I mean the really long and oversized shirts that are worn as dresses – are really in and fit the tomboy bill perfectly. Pair your tomboy dress with a puffer jacket and boots to complete your look.

5. Leather Trousers

Leather pants for tomboys
Image: Gettyimages

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

Skinny jeans and denim shirt for tomboys
Image: Gettyimages

Swing into the feminine side just a little bit with this outfit. Jeans are a signature boyish outfit. 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

Bold monochrome jean pants and jean jacket for tomboys
Image: Gettyimages

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

8. Flannels

Flannels with plaid shirt for tomboys
Image: Gettyimages

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

Plaid pantsuit for tomboys
Image: Gettyimages

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

10. Leather Jacket

Leather jacket with denim pants for tomboys
Image: Gettyimages

Leather jackets never fly under the radar when it comes to gender-neutral outfits, and they are here to stay.

11. Oversized Blazer

Oversized pastel blazer with bold buttons for tomboys
Image: Gettyimages

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

protip_icon 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

Bomber jacket with denim pants and boots for tomboys
Image: Gettyimages

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

Side stripe pants with oversized coat for tomboys
Image: Gettyimages

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

Business casuals with black tailored top for tomboys
Image: Gettyimages

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

Denim shorts with black crop top and denim jacket for tomboys
Image: Gettyimages

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 tomboyish look.

16. Tutu Skirt Or Dress

Black tutu dress with lapel collar and tie around for tomboys
Image: Gettyimages

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

Distressed gray denim with red hoodie and white sneakers for tomboys
Image: Gettyimages

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

Sweatshirt dress with thigh length boots for tomboys
Image: Gettyimages

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

Boyfriend shirt with skinny jeans for tomboys
Image: Gettyimages

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

Tomato red dress with gold accents in the neck paired with brown leather jacket for tomboys
Image: Gettyimages

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 genderqueer outfit 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 androgynous outfits 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

Tomboy outfits are all about androgynous style and playing with masculine fashion and silhouettes. It is a common misconception that tomboyish 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 clothing by adopting the norms of a true tomboy or changing them to meet our own. Tomboyish 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.
tomboy outfits

Image: Stable Diffusion/StyleCraze Design Team

From names to styles, get tips for the perfect tomboy look. Check out this video for the latest Korean tomboy outfit ideas!

Michelle Wagman

Michelle WagmanFashion Stylist

Michelle Wagman is a fashion industry entrepreneur with over 20 years of experience as a designer’s agent. She is also the editor-in-chief of FashionEdits, a fashion and lifestyle blog. She graduated from FIT with a degree in fashion merchandising and has worked with notable designers on 7th Avenue in NYC.read full bio

Latest Articles