Tomboy outfits are one of the greatest fashion looks and the best way to get a fresh and completely new look. Take a look at these 29 best tomboy outfits and get inspired!
How to Dress Like a Tomboy and Still Be Cute
If you’re not happy with your appearance, it can be hard to have confidence in other areas of your life. If you feel like you’re not feminine enough, but don’t want to dress like a girly girl either, tomboy fashion might be the way to go! It’s kind of like halfway between being feminine and masculine – and there are plenty of options available to help you look good without being too over-the-top about it.
1) Leather Jacket
This is a classic piece that every tomboy wardrobe needs. The options are endless with what you can wear it with, and whether you want to dress it up or keep it casual, a leather jacket is always an option. It’s also very durable and can last you several years depending on how often you wear it. A great purchase to make sure your tomboy outfit makes an impact!
2) Motorcycle Boots
It doesn’t matter if you’re a girl or boy, motorcycle boots are not only stylish but comfortable as well. Get yourself a pair of black motorcycle boots and you can wear them with your boyfriend’s jeans to create a very fashionable look. Or, pair your black motorcycle boots with shorts and skirts to create a more feminine look. Whatever style you choose, rest assured that every tomboy will enjoy wearing these ultra-stylish boots. And who said only girls could be tomboys?
3) Button-Up Shirt
In no way is a button-up shirt a tomboy outfit, but if you accessorize it correctly, it can be. This cool, casual look is great for a night out on town with your best friends or going to see some punk music at a bar. Tie your white button-up shirt around your waist and add black skinny jeans and converse shoes. Grab some red lipstick to finish off your outfit and you’re ready to go!
4) Denim Jeans
Denim jeans are a perfect tomboy outfit. Not only can you wear them year-round, but they’re super versatile too. Pair them with a basic shirt and baseball cap during casual weekend days, or dress them up with wedges, earrings, and a blazer to bring out your fun personality during special occasions like Halloween. Shop now.
5) Converse
Let your creativity run free in these converse shoes. A must-have for any tomboy clothing, these shoes are comfortable and trendy.
Converse shoes are very popular in the fashion world. They come in many colors and styles, such as All-Star, One Star, Jack Purcell, and Chuck Taylor. They are perfect for any girl who wants to be stylish and fun.
6) Glasses
With so many styles to choose from, it’s no wonder that glasses have remained a fashion staple throughout history. For an outfit with a scholarly edge, try a pair of thick-rimmed specs. With their monochromatic color schemes and classic design, they scream teacher or professor. Pair with a vintage dress and cardigan—and you’re set!
7) Snake Earrings
Necklaces are great, but if you’re dressing up as a tomboy for Halloween, skip wearing one and opt instead to wear snake earrings. Find similar ones here!
8) Shaggy Bob Haircut
This haircut is short on top, with hair that falls over your forehead and ears. To achieve it, use a large amount of product or cream to blow-dry your hair until it’s wet, then use a medium-sized round brush to dry it further and create volume. A few loose strands hanging in front of your face are perfect if you’re going for a tomboy look. Finish with hairspray.
9) Faux Fur Coat
You don’t have to be a girlie-girl to wear a fur coat. Throw on a faux-fur collar, or just buy an entire coat made of fake fur. Wear it with your black tank top and combat boots for a look that says I’m so not feminine, but I rock.
10) Boy Shorts
Instead of going with that fishnet miniskirt or high-waisted shorts, try boy shorts instead. Not only are they a bit more modest, but you can also wear them as pajamas after trick-or-treating is over! Just pair your choice of boy shorts with a graphic tee and some combat boots. You’ll have a fun outfit that will keep you cool and look cute at the same time. Don’t forget to accessorize!
11) Frayed Shorts
Since tomboys are often free spirits, it’s likely they don’t play by many rules. A frayed pair of jean shorts are great to wear on a night out. They’re fashionable and easy, two characteristics you want in your clothing if you want to be a tomboy. Add some biker boots and a tough t-shirt to complete your outfit. You can even wear some suspenders or a leather belt with metal studs as an accent piece!
12) Leather Trousers
Pants made from leather are a staple of many tomboys’ wardrobes. While they offer flexibility and comfort, they also give you a look that is uniquely masculine. If you want to wear leather pants, it’s best to choose ones in black or dark brown. You can also match them with shirts in other neutral colors—like white, tan, or beige—or a darker color like blue or purple.
13) Bold Monochromes
Show off your tomboy nature by dressing in monochromatic outfits. Monochromatic outfits can be bold and powerful or subtle and sweet. Either way, there’s a good chance it will help you stand out in a crowd (just make sure you pick an outfit that fits your figure and personality).
14) Flannels
Chunky knit sweaters as flannels work well on tomboys, they come in a variety of styles and colors, but what gives them that tomboy look is their loose and easy-going fit. Pick one up in black or grey and pair it with some distressed skinny jeans to complete your classic tomboy look. A pair of lace-up boots will finish off your outfit perfectly.
15) Oversized Blazer
The oversized blazer is a style that’s been popular since Giorgio Armani immortalized it in his collections in 1978. These days, oversized is considered a classic menswear look, so keep an eye out for oversized blazers at stores like Uniqlo and J.Crew, especially when shopping during sales.
16) Side Stripe Pants
Do you have a pair of side stripe pants? If not, it’s time to find them and make them your own. These skinny-fitting pants have stripes that go down one leg, opening up a world of outfit possibilities. Pull them on with a t-shirt and ankle boots, or with a frilly blouse and heels. The only downside is that these pants are usually pretty short—so if you’re tall (or even average height), they might not work for you.
17) Business Casuals
They may not be conventional (the term tomboy is anything but), but that doesn’t mean you can’t dress in a tomboy manner. If your favorite way to dress up is with some designer duds, then by all means—go ahead and look just as fancy as you want! But if you prefer comfort over style, here are some fun ways to wear what you love without sacrificing comfort…in true tomboy fashion.
18) Shorts And Crop Top
Now, you’re probably thinking that there is no way to make a crop top look masculine. You are wrong! You can either pair it with some baggy shorts (like I did) or if you have long enough hair you can tie it up into a ponytail or braid and leave your shirt untucked. With hair tied up, your outfit could easily be mistaken for just a plain t-shirt and jeans.
19) Tutu Skirt Or Dress
A tutu skirt is a flirty, feminine look that anyone can pull off. It’s also easy to make one yourself with a few yards of tulle. Simply cut it into a circle and secure it with elastic at your waistline. And if you want to go above and beyond, decorate it with ribbons, feathers, or flowers! Just remember: If you aren’t comfortable wearing one to work, don’t wear one on Halloween night!
20) Hoodie Dress
A hoodie dress is a cute, comfortable outfit that will keep you warm while you’re running errands or trick-or-treating. The perfect tomboy outfit can be dressed up with heels and a statement necklace if you’re headed to a party. Topped off with suspenders and knee-high socks, it’s also an easy costume for your next Halloween party.
21) One-Piece Dress
The one-piece dress is a classic option, whether it’s a short and flirty design or a long, elegant style. It’s perfect for tomboys of all ages and body types. Pair it with some cat ears (perhaps from an old costume?) and you’re ready to go!
22) Stud Earrings
There’s just something about tomboys that gives off a bad-ass vibe, right? It might be their easygoing nature or their laid-back approach to fashion. Whatever it is, stud earrings are a great accessory for tomboys of all ages. Here are some of our favorite pairs!
Try on boyfriend jeans
One of the best ways to look more like a tomboy is by donning jeans that are big and loose. Boyfriend jeans have gotten popular with women who want their clothing to be as baggy as possible, so try them on if you think they’ll fit.
Wear loose-fitting clothes
Loose-fitting clothes allow you to feel comfortable in what you’re wearing. Don’t worry about making sure your shirt is tucked into your jeans all day long. Don’t worry about whether your blouse matches your skirt, or if you can even see your shoes. Loose-fitting clothes are casual, laid back, and tend to be more comfortable than tight-fitting ones—especially if they don’t fit right!
Dungarees
If you don’t know what dungarees are, then it is likely that you don’t know what tomboys are. Dungarees look like denim pants worn by sailors. Pair them with a long sleeve tee shirt or a sweater for added comfort. You can even add a denim shirt if you want to wear something on your upper body or cover your shoulders in cold weather.
Jackets for Tomboy Outfits
You can never go wrong with a classic leather jacket. This always-in-style outerwear piece has been part of our wardrobes for decades and will surely still be there for many more years. Leather jackets can be paired with anything, from jeans and t-shirts to pencil skirts. Any girl (or guy) should own at least one leather jacket in their closet! If you don’t have one yet, make sure you get your hands on it soon!
Celebrity Style
Inspired by tomboys of Hollywood, like Avril Lavigne, Selena Gomez, and Dianna Agron, there is no shortage of men’s clothing being worn by stylish women today. However, it’s important not to get ahead of yourself—maintaining your femininity will keep you from looking out of place at work or while running errands. The key is to find clothes that fit your body type as well as your fashion sensibility.
Add a beanie to your outfits
By adding just one hat to your wardrobe, you can bring down your overall style quotient. Beanies are extremely versatile and help to keep you warm in winter or hide your greasy hair in summer. What’s more, beanies instantly add swag to any outfit that they’re worn with. What’s not there to love?
Dress like a tomboy with printed tees
One of my favorite ways to dress like a tomboy is with printed tees. Not only can you find some that fit your personality, but they also look pretty good on any body type. Plus, depending on your mood or where you’re headed, it can be easy to dress them up or down.