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How To Dress Like A Tomboy

Back in the day, the tomboy style was misconstrued as expressing sexual orientation and not caring about fashion. 

Nowadays, that view is seen as outdated, and a tomboy style is more about creating an androgynous look, one that is very in fashion at the moment. 

How To Dress Like A Tomboy

This style is about experimenting and playing around with pieces that move away from the conventional feminine fit and embracing masculine silhouettes.

This is already something we’re seeing in style today, with the introduction of loose-fitted jeans, and oversized clothing.

This article is going to be outlining certain pieces and outfits that you can play around with in order to create a tomboy style! 

Boy Shorts 

Slipping into a pair of men’s athleisure shorts is a great way to experiment with this masculine style. For your top half, try a button-down shirt that’s half-tucked in, or you can try a fitted cami or bodysuit.

If you’ve opted for the latter option, you can try layering and throwing a button-down over the fitted cami. 

This is a nice combination of both masculine and feminine styles, drawing attention to your top half. Pair with some converse, or sneakers of your choice, and this is the perfect tomboy look, with a hint of femininity if you’d still like a touch of it. 

Frayed Denim Shorts 

Frayed denim shorts that just hang onto your figure rather than hugging you tightly are also a great option if you want to experiment with the tomboy look. 

You can pair these with a graphic tee, or even a button-down. Pull your hair up into a messy bun and throw on some comfy sneakers and voilà! 


Overalls have really made their way back into our closets in recent years. The relaxed and comfortable fit of this staple item also resonates with the tomboy style. You can opt for the shorts or long pants version, and either one will work well for this style. 

You can wear a casual t-shirt underneath, or a knit sweater for the winter months. This outfit can be easily dressed up with some chunky jewelry, or even a wide-brimmed hat. 

Plaid Shirts 

Plaid flannel shirts are wonderful to look at and are a perfect addition to your wardrobe if you’re looking to play around with the tomboy look.  

Plaid will always add a masculine twist to any outfit, whether it’s a shirt or a dress, and you can play around with all kinds of color combinations, opting for some soft pastels, or bold, vibrant colors. 

You can even grab yourself an oversized plaid shirt and wear it as a dress. These are super flattering and fit the tomboy style perfectly! 

Oversized Jackets 

Oversize jackets have been around for a few years now, and whether they’re denim, puffy leather, or anything in between, their oversize fit can be very flattering on a feminine figure. 

It is important, however, to keep it in proportion with your size, as you don’t want the jacket to drown and overwhelm you. 

Try pairing your oversize jacket with skinny jeans for a nice contrast. If you really want to experiment with both masculine and feminine styles, try a pair of boot heels for an even more striking contrast.

If you want to go more tomboy, then some sneakers or even combat boots would fit the bill. 

Oversized T-Shirts 

The ‘borrowed my boyfriend’s t-shirt’ scenario has now become a style all on its own. There’s something about a feminine figure looking safe and comfortable in oversized clothing. 

When it comes to oversize T-shirts, you can have fun and experiment with all kinds of colors, patterns, and designs.

How To Dress Like A Tomboy

For the warmer months, wear your favorite one with a pair of distressed denim shorts, along with some sneakers. 

For the winter months, you can tuck your oversized t-shirt into some skinny jeans and throw on an oversized jacket of your choice. This is another outfit that combines both styles effortlessly. 

Loose-Fitted Jeans 

In recent times, we are seeing fewer women wearing skinny jeans. While they will never go out of style completely, women are adopting a more baggy and loose style with their jeans, with many popular clothing brands introducing all kinds of styles that are the polar opposite of skinny jeans. 

These include ‘boyfriend jeans’ which have a very slouchy and relaxed fit, hanging loosely all over. There are also ‘mom jeans’, which depict the combination of both masculine and feminine perfectly.

They are high-waisted with tapered legs, allowing them to follow the natural silhouette of the legs without hugging them tightly. 

They offer a relaxed, loose fit, while still showing off some shape. Aside from these two styles, there are a variety of jeans available now, such as wide-leg, straight-leg, and flares, among many others. 

While they are all different, the main thing they have in common is they are not fitted throughout the entire leg, they offer some bagginess. 

These jeans are great at embracing that masculine style, while not completely dismissing some aspects of the feminine fit. 

Pairing these jeans with a loosely fitted tee, tucked into the waistline, or even an oversize shirt tucked in, is a great way to experiment with the tomboy style. 


Playing around with shoes that are more masculine is a great way to experiment with this kind of style. Some classic converse is a great place to start, especially the black versions.

They are also super versatile and can be worn with jeans, shorts, dresses, you name it! 

You can also try some loafers, which are also very versatile and come in a variety of styles and colors. 

If you’d like to step up your game, try some combat boots such as Doc Martens.

These, paired with a leather jacket and some loose-fitted jeans of your choice, will really give you the chance to experiment with a more masculine style of clothing. 

Final Thoughts 

As mentioned earlier, the tomboy style nowadays is about experimenting with a more conventional masculine style. 

While years ago this was seen as girls being confused about their sexuality, nowadays, a more masculine style of clothing is seen as fashionable and in style. 

Jenna Reign
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