Tomboy style: 47 outfits ideas in a masculine-feminine style.

Follow these fashion matching methods to recreate the Tomboy Style. This style guide will show you how to achieve the perfect mix of masculine and feminine in your own personal style.

Women’s fashion got slowly inspired by menswear at first. Although it was seen as odd or even shocking 100 years ago, that’s no longer the case. The modern masculine-feminine style speaks to those of us who appreciate classic cuts and comfort, but would still like to express their femininity to a certain degree.

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Tomboy Style Icons

We all know that Coco Chanel became famous for liberating women from corsets and long uncomfortable skirts, by offering them cozy knits and trousers instead. But not a lot of people know about another style icon from the US that was probably the first true Tomboy fashionista. And that is the fearless and groundbreaking aviator Amelia Earhart. 

Besides achieving several aviation records including becoming the first woman to fly across the Atlantic, she also introduced the world to her unique personal style. A pioneer of the feminine-masculine style, or Tomboy style, she wore pieces like leather bomber jackets, tailored trousers, smart loafers and sleek neckties. While brown, white, tan and black colored clothing made up a majority of her wardrobe, Amelia managed to keep it anything but boring. She wasn’t afraid to wear a monochromatic neutral look or to even mix multiple neutrals together for one stylish outfit. For the 1930s it was considered extravagant. 

Other Tomboy fashion icons that you all probably know were beautiful movie stars Katharine Hepburn and Marlene Dietrich. Hepburn favored menswear-inspired, collared shirts, blazers, loafers, simple makeup and of course trousers. Marlene Dietrich’s most famous looks were the ones where she wore masculine three-piece suits to create a distinctly androgynous look that helped to revolutionize and redefine women’s fashion. 

Tomboy Fashion Style Essentials

Here are some essential items that any Tomboy woman has in her wardrobe. Please, note that we are talking here only about the fit and style of the item. The colours, patterns, and textures will vary depending on your personal style.

TOMBOY STYLE TROUSERS

The most common cut for tomboy trousers is a classic one with a crease and natural medium waist. The best material for this cut is wool. It just keeps the shape the best, no matter what type you choose, a slim cigarette or wide-leg. For a more business feel, pair them with a cotton shirt and a pair of oxfords. If you want to add some sex appeal, try a high waisted pair with a silk, slightly loose blouse and a pair of loafers.

TOMBOY STYLE SHIRTS

The most functional and comfortable cut for a tomboy style shirt is a slightly loose, boyish shape. Depending on your mood and stylistic direction, you can choose to have similar shirts but in different colours and materials. Organic cotton shirts look great in white, light blue and black. Tencel shirts have a slightly smoother texture and look good in checkered patterns or stripes. SIlk blouses have that beautiful luxurious shine, so camel, grey, navy and black can be the best options for everyday wear. 

TOMBOY STYLE SWEATER

I’d say that you should try and opt for 3 kinds of sweaters, the thick, medium thick and thin ones. The best cuts are straight or loose, both are quite versatile. The thick sweater looks a bit more casual, so this is something you can wear with a pair of trousers and trainers, or a pair of jeans and oxfords. Besides, it’s a perfect layering piece that you can wear on top of your blouses and dresses for extra warmth without adding bulk. The medium thick sweater can be made of alpaca wool, or cashmere. This is something you can wear solo as a top. The thin sweater is usually made of merino wool, which is very warm and is perfect for wearing with a blazer in colder days.

TOMBOY STYLE T-SHIRTS 

Another essential item in a Tomboy’s wardrobe is a slightly loose t-shirt. This is something you wear with your suits, blazers or sweaters. Don’t think too much about it, and go for a monochrome and a medium heavy fabric like linen, organic cotton or tencel. 

TOMBOY STYLE JEANS

The most versatile option of jeans are medium rise, straight and clean cut in dark colours like dark blue or black. This model will fit perfectly with a blazer and loafers. Or you can dress it up for an evening and pair it with a silk blouse and high heels. 

TOMBOY STYLE BLAZERS

A well made wool blazer is that one item that will add more structure, elegance and chic to your outfits. The most versatile options would be black, navy, grey or even camel colours. To avoid a stiff and business look, add a little bit of flirting with your styling. For example, add a red lipstick, unbuttoned blouse, some jewellery or colour accent accessories.  

TOMBOY STYLE DRESSES

Even though the majority of items in this style are inspired by menswear, you still can wear a dress. Just choose something easy, comfortable and not too girly. For example, you can try a simple straight cut, shirt dress or something more architectural. 

TOMBOY STYLE OUTERWEAR

Here we have some options. The well-cut wool coat is great for colder months. Choose classic cuts, one or double-breasted, straight silhouettes and knee or midi length. For Autumn and Spring, the most practical option will be a trenchcoat. You can go for a classic cut and colour or find a vintage model that maybe is slightly oversized and slightly faded in colour. This will make your look a little less serious and more casual. Besides these classics, you can also opt for a leather biker jacket or an oversized bomber. 

TOMBOY STYLE SHOES & ACCESSORIES

For a more classic look I’d recommend styling your outfits with loafers, oxfords or brogues. Black or brown, you decide. For colder days it could be a pair of chelsea boots or lace-up boots. Of course, you can also opt for something more interesting or feminine. For example, a snakeskin pattern looks great with monochrome outfits. 

As most of the items in this style have a more minimal, architectural design, your handbag should also have a structured style in a medium size or smaller. But here you can play with colour and use it as an accent or a neutral element.

The perfect jewellery for this style is something that is informal, wearable, discreet and personal.

Tomboy Style Capsule Wardrobe.

The tomboy capsule wardrobe I’ve created consists of 7 tops and 1 blazer, 4 bottoms, 1 dress, 1 jumpsuit, 2 jackets, 4 pairs of shoes and a bag. When I mix all these items together I get 47 fully interchangeable outfit combinations. For my colour palette I chose cold colours: 5 neutrals and 4 bold colours. I love to play with different shades of the same colour. It gives a personal touch and creates more texture.

Talking about the texture. I made sure to choose different materials. I have different textures of wool, cotton, silk, denim and tencel. I think this way I have more versatility and it just looks more interesting. I added 3 pairs of shoes. They are quite simple and practical, but that is the point. All three pairs can be worn with any outfit here, it all depends on your mood and the weather, I guess.

I’ve also added 2 jackets. One is shorter and more casual, so it can be worn with any outfit that doesn’t include a blazer. And another one is long and thick. It’s also spacious enough to wear with a blazer underneath. 

Overall, I think this wardrobe came out to be stylish, versatile and practical. A wardrobe that would be perfect for a modern gentlewoman that appreciates timeless elegant design, comfort and simplicity.

Tomboy Wonder Wardrobe

I hope this video and blog post gave you ideas and inspiration for your own fashion style and wardrobe.

Please, let me know in the comments what are some Tomboy items or looks that you have in your wardrobe. I feel like this style is not represented enough and we can all get some inspiration from each other!

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