The Tomboy Style Illustrated And The Cute Tomboy Outfits You Don’t Want To Miss

The androgynous nature of tomboy style fashion is always relevant. Who among you hasn’t flirted with this look at some time? You might be surprised to learn that the word dates back to the sixteenth century, but it came into its own, bigtime, via the garçonnes of the 1930s Jazz Age, with women who adopted what Vogue termed a “trim and boyish” look.

So for inspiration, we can stretch back to Marlene Dietrich, Greta Garbo, Coco Chanel and beyond, and then fast forward to Rita Ora, Alexa Chung, Ellie Goulding and last but never least, Cara Delevingne, to find that the tomboy style is alive and well and living as supermodels and the like.

Reference Diane Keaton in Annie Hall for cool ways to wear waistcoats and ties! It has the definite advantage of feeding into every style – at the moment, it’s a natural fit with the menswear trend, for example – so let its eternal appeal inform your choices every season.

Boxy jackets and laceless combat boots tomboy style clothing will suit cooler days, while you can switch from day to night by swapping a blazer for a tailored jacket and pumps. That’s also the witching hour to add stilettos to sportswear to avoid actually looking like a boy, unless you want to, of course. Further enhance your girly roots by offsetting potentially masculine lines with cute floral prints, jewellery, or brassy buttons.

Get back to combat boots for a dream combo with leather shorts or denim cut-offs, or pair a sweatshirt and torn jeans with trainers. Roll your skinnies and work them with a button-down shirt in classic tomboy style. Conjure up just the right image with overalls and a white tee, but subvert the look with a faux-fur jacket. Throw a hoodie over slouchy trousers and sneakers, or top boyfriend jeans and a loose blouse with a fedora.

Don’t imagine that you can leave chic behind with the tomboy look, though. Gwen Stefani understands this (as she grasps so much else) when she steps out in ripped jeans, a black graphic tee and white-framed sunnies. Adapt your own tomboy outfit with a bomber and a baseball cap, trucker hat or the ever-faithful beanie.

We’re thankful that the style’s become a lot more playful since the 1500s, and that it’s developed a freer tomboy style since the thirties. Nowadays you can let loose your inner tomboy without giving up being cute – the best of both worlds, don’t you agree?

The featured photo is of Ellen Claesson: She is keeping it to the basics, wearing a beige coat, a blue knit jumper paired with a long white T-shirt, jeans and a pair of sneakers

Kaitlyn Ham looks ultra dapper in this beautiful tomboy style two piece, paired with sneakers and a simple black bralette beneath the blazer. There is no look more androgynous than wearing a suit! Blazer: Ellery, Trousers: Topshop Boutique, Sneakers: Wings + Horns, Bag: Givenchy.

Kaitlyn Ham looks ultra dapper in this beautiful tomboy style two piece, paired with sneakers and a simple black bralette beneath the blazer. There is no look more androgynous than wearing a suit!

Blazer: Ellery, Trousers: Topshop Boutique, Sneakers: Wings + Horns, Bag: Givenchy.

Combat boots are arguably the ultimate must-have for the tomboys! Jacqueline Mikuta pairs these edgy lace ups with distressed denim mom jeans and an oversized blazer from VILA, oozing style and swagger! Blazer/Sweater/Shirt: VILA, Jeans: Bershka, Boots: Esprit, Bag: Ganni.

Combat boots are arguably the ultimate must-have for the tomboys! Jacqueline Mikuta pairs these edgy lace ups with distressed denim mom jeans and an oversized blazer from VILA, oozing style and swagger!

Blazer/Sweater/Shirt: VILA, Jeans: Bershka, Boots: Esprit, Bag: Ganni.

Camille Callen dares to wear double leather, and the result is tomboy heaven. Shirt: Sheinside, Pullover: Pimkie, Trousers: Mango.

Camille Callen dares to wear double leather, and the result is tomboy heaven.

Shirt: Sheinside, Pullover: Pimkie, Trousers: Mango.

Team an oversized blazer with matching trousers and sneakers for a casual yet edgy effect. Via modernlegacy. Blazer: Ellery, Trousers: Topshop Boutique, Sneakers: Wings + Horns.

Team an oversized blazer with matching trousers and sneakers for a casual yet edgy effect. Via modernlegacy.

Blazer: Ellery, Trousers: Topshop Boutique, Sneakers: Wings + Horns.

Camille Callen looks effortlessly chic in grey slacks and fresh white sneakers; the ultimate tomboy look. Top; Zara, Trousers; Mango

Camille Callen looks effortlessly chic in grey slacks and fresh white sneakers; the ultimate tomboy look.

Top; Zara, Trousers; Mango.

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Mix it up with this button up long sleeved tee, jeans and a cute bag. Via Christine Andrew 

Shirt: Ily Couture, Jeans: Nordstrom, Bag: Ssense

The biker jacket, ripped jeans and Converse sneakers remains in the very top of the Tomboy lookbook. Via Laura Dittrich Jacket: BLK Denim, Sneakers: Converse Sneakers, Jeans: Zara

The biker jacket, ripped jeans and Converse sneakers remains in the very top of the Tomboy lookbook. Via Laura Dittrich

Jacket: BLK Denim, Sneakers: Converse Sneakers, Jeans: Zara

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Rebecca Laurey is looking stylish in these classic skinnies with a leather jacket!

Jeans: Levis, Jacket: BLK

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Black skinnies here to stay – pair them with a white tee and leather jacket for the classic look. Via Anine Bing

Jeans: Anine Bing, Jacket: Anine Bing, Tee: Anine Bing

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Carmen Hamilton is looking unbelievably sophisticated in this grey vest suit!

Suit: Rag & Bone, Shoes: Acne

Basics: Shorts, leather jacket and high-tops to creating an easy Tomboy Style Outfit. Via Lucy Williams T-shirt: Toteme, Shorts: Free People, Trainers: Vans, Leather Jacket: Belstaff

Basics: Shorts, leather jacket and high-tops to creating an easy Tomboy Style Outfit. Via Lucy Williams

T-shirt: Toteme, Shorts: Free People, Trainers: Vans, Leather Jacket: Belstaff

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If you’re looking for a smart casual look, why not take inspiration from Kaitlyn Ham with these black leather trousers, white sneakers and white shirt!

White Shirt: OSKAR, Leather Pants: Bassike,  Blazer: Dries Van Noten, Sneakers: Wings + Horns

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Lisa Hamilton pulls off the ultimate tomboy outfit with ripped skinny jeans, a baggy stripy tee and black ankle boots!

Jeans: Shopbop, Coat: Zara, Tee: Fifth Label, Shoes: Isabel Anselmi

Taking the military style to the next level. Military green is still going strong. Via Natalia Cabezas Shirt/Trousers: Zara, Bag: Steve Madden

Taking the military style to the next level. Military green is still going strong. Via Natalia Cabezas

Shirt/Trousers: Zara, Bag: Steve Madden

Pale blue shirt, pinstripe pants and loafers. Via Kamila Leciak Shirt: Promod, Loafers: Parfois, Sunglasses - Fossil

Pale blue shirt, pinstripe pants and loafers. Via Kamila Leciak

Shirt: Promod, Loafers: Parfois, Sunglasses: Fossil

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Kate Arends pulls of a simple yet classic look of a plain white shirt with grey trousers and trainers!

Shops: not specified.

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A plain yet striking combination of boyfriend jeans and a white tee. Via Katherine

Jeans: Levi, Shoes: Vans, Top: AS Colour

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Laura Dittrich shows off one of our favourite looks: distressed boyfriend jeans with a complementing white tee and black blazer.

Sneakers: Adidas, Jeans: Zara, Shirt: H&M, Blazer: Zara, Bag: Proenza Schouler

So tomboy, but Victoria Tornegren still manages to look cute Jacket: FWSS, Shoes: Converse, T- Shirt: Acne, Jeans Asos

So tomboy, but Victoria Tornegren still manages to look cute

Jacket: FWSS, Shoes: Converse, T- Shirt: Acne, Jeans Asos

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We love Victoria Tornegren’s boyfriend jeans, black jumper and converse – the perfect look!

Zoé Alalouch illustrating the tomboy style perfectly with a pair of distressed denim jeans, an oversized black cardigan, plain white tee and sneakers Jeans: Meltin Pot, Cardigan: H&M, Tee: Petit Bateau, Shoes: Golden Goose

Zoé Alalouch illustrating the tomboy style perfectly with a pair of distressed denim jeans, an oversized black cardigan, plain white tee and sneakers

Jeans: Meltin Pot, Cardigan: H&M, Tee: Petit Bateau, Shoes: Golden Goose

Carmen Hamilton in a tomboy style inspired outfit, oversized turtleneck sweater and pinstripe ash grey trousers Sweater: Country Road

Carmen Hamilton in a tomboy style inspired outfit, oversized turtleneck sweater and pinstripe ash grey trousers

Sweater: Country Road

Christina Caradona is one of the ultimate tomboy style bloggers. Here is seen wearing a white top and jeans and burgundy men’s shoes Top: Edun, Jeans: A Gold E, Shoes: Mamut

Christina Caradona is one of the ultimate tomboy style bloggers. Here she is seen wearing a white top and jeans and burgundy men’s shoes

Top: Edun, Jeans: A Gold E, Shoes: Mamut

Tomboy Fashion Style: Mary is wearing a tank top and skinny jeans from Current Elliott

Tomboy Fashion Style: Mary is wearing a tank top and skinny jeans from Current Elliott

Tomboy Fashion: Tine Andrea is wearing a pair of black Weekday skinny jeans, leather ankle boots and jacket from Zara with a Gant white shirt

Tomboy Fashion: Tine Andrea is wearing a pair of black Weekday skinny jeans, leather ankle boots and jacket from Zara with a Gant white shirt

Edgy Tomboy Style: Victoria Tornegren is wearing a pair of Gina Tricot boyfriend jeans with a plain white top and biker jacket from Topshop

Edgy Tomboy Style: Victoria Tornegren is wearing a pair of Gina Tricot boyfriend jeans with a plain white top and biker jacket from Topshop

The is classic tomboy style dress up Via unknown fashion blogger

The is classic tomboy style dress up Via unknown fashion blogger

A very smart tomboy outfit. Photography via Scotch and Soda

A very smart tomboy outfit. Photography via Scotch and Soda

The picture perfect Tomboy Look. Photography via Victoria Tornegren

Victoria Tornegren is pulling it off perfectly. Maxi coat, boyfriend jeans and Adidas sneakers. Classic.

A true menswear inspired outfit. It is the grey straight cut coat and hat that does it. Photography via Julie Sarinana

A truly menswear inspired outfit. It is the grey straight cut coat and hat that does it. Photography via Julie Sarinana

A simple white shirt underneath a grey slightly oversized sweater paired a pair of black skinny jeans can be easy way to achieve the tomboy look. Photography Via Mary Seng

A simple white shirt underneath a grey slightly oversized sweater paired with black skinny jeans can be an easy way to achieve the tomboy look. Photography Via Mary Seng