There’s something irresistible about throwing on a men’s shirt with a pair of leggings. It’s hard to pinpoint exactly what it is. The cross-dresser in all of us? Or maybe we all just love turning an ordinary piece of men’s apparel into an extraordinary accessory for ladies. With that in mind, we ventured to Goodwill, grabbed a basic men’s shirt, and enlisted resident stylist Misty Spinney‘s fashion expertise to craft 10 killer looks.

1. Skinny Jeans and a Belt

This look is perfect for everyday, and gets style points from a super hot belt and pair of skinny jeans.

We rolled up the sleeves to give the shirt a little more shape, and paired the look with strappy leather sandals.

2. Sassy Cargo

For this look, we kept Brit’s sleeves rolled up and simply tied the shirt to expose a little sassy midriff.

Love these little bootie sandals to complete the look.

3. Strapless Mini Dress

That’s right. You can turn a men’s shirt into a strapless dress! Perfect for a modern cowgirl look.

First, button up the shirt without the sleeves on. Take the sleeves and twist them, then criss cross them around your back. Bring them back to the front, tie a little knot, and you’re done!

4. 90s Hipster

Hipsters were around in the 90s, we promise. This look takes the classic look of a checkered shirt, Converse, and a plaid shirt and updates it with a little suspender action.

Clip the suspenders directly onto the shirt and see what shape works best for you.

5. I’m On A Boat

A pair of boat shoes, pinstripe pants, and a ruffled up shirt are all you need to channel your inner boat maven.

To ruffle the shirt we did two things: First, put a rubber band around the sleeve and blouse it out to create a little bubble. For the waist ruffle, use a safety pin to ruche on both sides.

6. City Girl

Black leggings and boots are every city girl’s go-tos. Add a men’s shirt and hip slung belt to shake things up a bit.

We’re kind of obsessed with this belt! It’s got tons of little loops so you can wear it high-waisted, hip-slung, and anywhere in between.

7. She Means Business

A boss in the boardroom? Why yes. Tuck your shirt into a high waisted skirt, add a simple thick black belt and throw on your hottest black heels.

8. Day n’ Night

An ideal look if you’re starting your day at the office and ending it at a cocktail party, art opening, or concert.

Underneath the shirt we’ve got a lace bodice that peeks out ever so playfully. Tuck the bodice and shirt into a pair of black trousers, and throw a long necklace over the whole look.

9. Bohemian Chic

Definitely the hippiest number on here, this look pairs good old boot leg corduroys with a DIY tube top!

To create the top, fold the collar of the shirt into the inside, creating a semi shelf bra. Take the sleeves around in the back, and tie up in the front, like the strapless dress.

10. T-Shirt and Jeans Upgrade

Nothing beats a t-shirt and jeans. Upgrade your look by going for a boldly hued pair of red jean and adding an old school t-shirt. Tuck in the color of your button down to create more of a blazer look.

This is a great look for a Saturday in the park, and we love any reason to bring back vintage tees that don’t quite work on their own.

Got any tips and tricks of your own for turning men’s apparel into women’s? If you give any of these a try, send us photos! And if you have specific questions about any of the looks above, leave a note in the comments below.

Anjelika Temple
As Chief Creative Officer and Founding Partner at Brit + Co, Anjelika Temple brings her voracious consumption of all things creative and colorful to DIY projects, geeky gadgetry finds and more. When she's not DIY-ing her heart out, you'll find her throwing dinner parties with friends or adventuring with her husband David, their daughter Anokhi, and their silly dog Turkey.