Tomboy Outfit Ideas 15 Tips How to Dress Like a Tomboy

Written by

Olivia Davis

Senior Fashion Editor

Reviewed by

Olivia Davis

Senior Fashion Editor

Updated Apr 14, 2026

Most people think tomboy style is just about throwing on baggy clothes and calling it a day — but honestly, that’s how you end up looking sloppy instead of cool. Real tomboy style has its own rules about fit, proportion, and styling that make all the difference between looking intentionally cool and accidentally messy.

Essential Accessories

The main accessories are hats and ties. Trilbies are a perfect androgynous hat for a perfect look. Chunky, colourful ties are brilliant for breaking up a plain-coloured button-up shirt.

Bottoms

You might also like

How To Dress In Your Twenties? 20 Outfit Ideas & Styling Tips

How To Dress Like Wednesday Addams? 20 Best Outfits + Tips

How to Dress as a Preppy Girl? 31 Outfit Ideas & Styling Tips

22 White Bodycon Dress Outfit Ideas with Styling Tips

How To Wear A Slip Dress ? 21 Outfit Ideas & Styling Tips

How to Dress Goth? 12 Outfit Ideas & Styling Tips

20 Best Suede Dress Outfit Ideas with Styling Tips

How To Wear Maxis Dress? 17 Outfit Ideas and Styling Tips

Jeans are the traditional style of legwear. There is a style called ‘boyfriend’ jeans which are very popular in teenage scenarios; however, skinnies are also acceptable.

Why not pair skinnies with colored sneakers? Why not match plaid sneakers with a plaid shirt? Plaid is a beautiful pattern that can be easily paired with a plain blazer.

Building Your Foundation Pieces

Start with five key items: well-fitted straight-leg jeans, a quality white tee, a denim jacket, canvas sneakers, and a simple hoodie or sweatshirt. These pieces work together in countless combinations and provide the neutral base you need to experiment with different styling approaches.

How to Get A Tomboy Look

# 12 – Boyfriend Jeans

Boyfriend jeans have been making rounds in the fashion world for some time now. A high bun and shoulder bag are good enough to complete the look. Whenever you are dressing up as a tomboy only sneakers or boots will do as shoe wear.

# 11 – Shirt Around the Waist

A sleeveless tank top with skin-tight leather pants, a flannel shirt to cover yourself up from the cold and a beanie for extra points. Contrasting shoes will be needed hence the white sneakers.

# 9 – Jackets

Denim shorts with a sweatshirt and a blue jacket with ankle-high black boots. A good big shoulder bag will be enough you have some things to carry around with a red beanie and no makeup.

# 6 – With a Skirt & Beanie

Plaid and pleated skirt with a plain top and black heeled boots. The usage of more classic colors in this clothing style is very important. To finalize the whole look, you may add a beanie and stockings and, finally wear boots to complete the look.

#2 – With Graphic Tees

You can style a graphic tee with a pair of high-waisted mom jeans and white sneakers or you can boss it up with oversized monochrome suits. Graphic tees look fierce and cool under a nice denim jacket.