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How To Dress Like A Tomboy: 10 Outfit Ideas

At this point the tomboy style has been around for decades, and it’s not going out of style any time soon.

The tomboy look is not only synonymous with freedom and being able to express yourself in whichever way you like, it is also extremely stylish with a huge variety of outfits you can customize and combine to pull off the fit.

How to Dress Like a Tomboy 91 Outfit Ideas

Rather than bright pink colors, high heels and long dresses, these outfits take a few outfit ideas from the male wardrobe to create a style that is casual and relaxed but also extremely comfortable.

Whether you are just intrigued or want to find a tomboy style that would suit you, below we have compiled a huge range of different tomboy styles and outfits to match each piece of clothing that are the most trendy and popular today, so keep reading to find out all about them.

Who knows, you might just find a new style that becomes one of your favorites. 


Brown, back and dark gray caps are some of the easiest tomboy fits for creating a low key casual look.

Baseball caps are the go to option, you can pick either winter, washed, rugged, snap back or even vintage baseball caps for their ripped stylish look. 

Also try out some branded caps too such as with symbols or band names on them to add even more style to this part of the outfit.


An alternative to a cap which is still hugely comfortable and trendy, beanies are the perfect fit choice for colder weather, but can also be worn in the summer as a relaxed choice.

While much of a tomboy fit can be a bit on the darker side, with beanies you have a lot more choice.

If you are fitted in mostly black for example you can try a washed light great beanie to add a hint of color, or if you are rocking a denim jacket or over shirt or maybe a casual oversized hoodie, an orange or green beanie can add that perfect extra hint of color.

Beanies will go with mostly any outfits, so feel free to find a color and material that suits you. 


Some of the beauty of the tomboy look is how it both feels very comfortable and still looks trendy with no need to fit into a tight dress or skirt to look good.

This goes the same with t-shirts, one way you can style this is simply by wearing a t- shirt you like the feel of, just try to make sure the colors are very desaturated or moochomatic to really give it that casual and relaxed look.

Another great idea is oversized t-shirts, these can be left untucked to give a free flowing and lively look or they can be tucked into some ripped black or blue jeans for a cool fit. 

You can also try styling an oversized shirt as a dress if it is long enough and reaches just above the knee. This is a great choice for taking a feminine fit, but putting your own spin on it.

You can style these longer t-shirts with sneakers and whitw socks to really give off a boyish look, or some black stockings to add a hint of femininity to this casual style. 

You could aso match a large t-shirt with some ankle boots for a comfy fit that you can be sure you won’t get too cold in. 

Some ideas for t-shirt designs include pop and rock bands. The symbols or album covers of popular bands are very recognisable and add a huge amount of familiar style to any outfit. 

Oversized Sweaters And Jumpers

A tomboy outfit is usually recognised by it’s spacious and baggy style, however this also makes them very comfy such is the case with oversized sweaters and jumpers. 

Easy to throw on and in a variety of designs and colors, you can match a dark green or gray oversized sweater perfectly with darker jeans or jogging bottoms and can be finished off easily with either white or dark shoes.

For more color, you can also try lighter shades of blue and yellow sweaters and jumpers mixed with lighter washed out jeans to still maintain the tomboy look but add a bit more vibrance to the outfit too.

Lighter baggy sweaters also go great with shorts and some darker sneakers for a tomboy look that is perfect for the summer. 

Finished off with a beanie or cap, this is a very casual part of the fit that can be matched with most other variations. 


Hoodies are a classic in the tomboy style and they too should definitely be considered for a warm and comfy option.

Oversized hoodies both ooze style and are incredibly comfy and spacious to wear. White and black are again the go to colors, however darker browns, greens and blues can also make for a unique outfit.

Hoodies with wide and spacious hoods are the perfect choice for something both feels and looks comfy, and try matching this with a black cap to pull off a very relaxed fit that you can ensure will keep you warm.

You could even add another layer if you want to introduce some more designs or if it’s a particularly chilly day, however this won’t need to be anything too thick.

A breezy over shirt, black loose track jacket or very thin dark coat are perfect choices to match with a hoodie along with a cap to really finish the outfit off. 


In today’s day and age it’s hard to find pants that boys wear more than jeans, especially in black.

A pair of black skinny jeans are a great outfit choice for something that is noticeable but not bright or over the top, and is an easy idea to put together with an oversized or just regular t-shirt.

Ripped black jeans are even better and give a bit of an edgier look to the outfit if that is what you’re looking for. 

Pairing darker jeans with either white or black sneakers is also the best way to color match the outfit and finish it off. 

If you choose to wear an over jacket, try either denim or leather to smoothly mix with a pair of black jeans. 

You can also opt for light washed jeans for a bit more of a vintage and retro look, these can similarly be matched with white and dark shoes but also other colors such as gray or brown, giving you some variety if you have a specific pair of shoes you want to match. 

How to Dress Like a Tomboy 91 Outfit Ideas (1)


If there is one piece of clothing guys wear all the time that many women wish they could throw on just as easily, it’s sweatpants.

Luckily the tomboy look gives you the perfect excuse as some gray sweatpants will go great with a darker oversized top or sweater.

These are often a bit baggier and can look stylish and casual when paired with some white ankle socks and darker smaller shoes such as a pair of Vans.

For a sportier look that still fits the tomboy style and seems relaxed, try some tighter fitting black sweatpants mixed with an oversized top or sweater and black or white cap.

This is a comfy fit ready for any occasion that is perfect for lovers of the darker colors. 


The aim here is again dark colors.

Black shoes, or at least dark with white designs surrounding them, are often the go to option that will ensure your outfit keeps that more low key tomboy look without being over the top and as is if you’re trying to make a huge fashion statement.

Luckily there are quite a few darker designs that can be tried out, Vans and All Stars are some of the easier choices to find and put together that are on the darker side but still have several designs to choose from, being perfect to match up with some ripped black jeans, gray joggers or even washed out lighter jeans. 

The chunkier Doc Martens are also a great option that screams style and uniqueness.

Because of their bigger size, they are usually more suited to the chiller months and seasons, however they can too be paired up with black or slightly lighter jeans for a comfy look.

Timberlands are also a thicker option perfect for the winter months that mixes extremely well with both regular and ripped black jeans. 

In terms of socks, white socks will be your go to for essentially any shoe color. It’s a great color matcher and is not too bright to the point of ruining your outfit.

Ankle socks can also be considered to really nail a more edgy look that can be great with ripped jeans or sweatpants.

Suits & Blazers

You don’t need to ditch the tomboy look when you need to go to work or a formal meeting.

There are many ways to retain this style and make it suitable for the workplace in no time, and suits usually seen on men are the perfect and easiest way.

Rather than looking casual and unbothered, suits instantly give off a sophisticated impression and are a great polished option to feel comfortable wearing in more formal situations.

The classic option is a waist length open black suit with a buttoned down white shirt. This is a very common fit among men but it works all the same here in giving a smart and proper look that is still stylish and easy to put together.

Gray suits also work great with this, you can either choose to mix it with a buttoned down white shirt, or a black shirt with even a tie if you want to really nail that formal tomboy look. 

Darker blazers are also a great option, matching perfectly with some straight leg trousers or leggings. Try matching both suits and blazers for dark slip on or whole size shoes.

To add some edge to the outfit try opting for either sneakers or loafers, or high heels if you want to add some more femininity into the fit. 


Some additions to finish off a tomboy look include aviator sunglasses that are extremely trendy in the summer months. 

A sport watch or casual loose bracelets are also small features that will go a long way in creating a low key look that can help add those finishing touches to a tomboy outfit.


Not everyone wants to take the enormous amount of time to prepare a hyper feminine look, and there’s nothing wrong with that at all, that’s why the tomboy style exists and with these range of ideas in mind, don’t hesitate to mix some outfit ideas and see what fits you feel most comfortable wearing for the next few months.
Jenna Reign
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