Style File: How to Wear One Shirt, 10 Different Ways

A simple button-down shirt (whether it’s fitted or oversized, women’s or men’s, coloured or neutral) is a must-have in every wardrobe. Besides being quintessentially classic, it’s the perfect transition piece – from casual to formal, from work to play, from serious to fun. And the best part is it’s totally customizable to your own personality, or your many personalities.

With a little creativity, the right undergarments or just the perfect amount of confidence, your one simple shirt you have hanging up in your closet just became ten different shirts. And maybe even more! After all, it’s all about having fun with how you style it and what works best for you.

Stylist and fashion writer Stephanie Ramlogan is queen of versatility when it comes to her wardrobe – and she captured all of her favourite ways to wear a simple buttoned shirt. (Spoiler alert: there are way more than ten!)



Starting off simple, fold the bottom half of the shirt up for a more-fitted cropped look, and button the shirt along your back for a high-neck, super-chic look.


Skip the arms! Button this shirt up as a strapless around your bust, and then tie the arms where they naturally fall under the bust). You can leave it criss-crossed in front or wrap them around the back.


Put on the shirt as normal, except tucking one arm below your armpit. Button the top button, and wrap the free shirt arm around your back and tuck into the shirt buttons. Use the button on the cuff to button into a body button-hole to keep the look together.


Start this one like “look ma, no arms” – by buttoning the shirt as a strapless, except turn it around so that the buttons are in the back. Cross the shirt arms behind your back, and then using the buttons on the cuff, button them into each other and let the arms hang naturally on your body.


In the same vain as “back flip”, start with a strapless -buttons-in-the-back shirt. Tie the arms in front once and pull the remainder behind the back. There, you can knot it or follow suit with “back flip” and button the cuffs into each other.


Starting with a backwards strapless, take the shirt arms and criss cross them and tie around your neck in a psuedo-halter. Adjust until comfortable, and let the shirt hang accordingly.


It’s time to crop this top! Put on the shirt as you normally would, but instead of buttoning, you’ll be tying it! Pull it as high or low as you feel comfortable wearing it, and double knot it. Then, have fun with the arms – wear it cuffed or long, it’s all your preference!


Who said you can only wear a shirt as a shirt? Paired with a cute bra, crop top or under-shirt, this is the perfect jumper! Start by buttoning the top button around your waist. You can button as low or high as you’d like. Take the shirt arms and either button or tie around your neck for this unexpected look.


A one-shoulder in reverse! Put the shirt on backwards, leaving one arm out. Tuck the arm into the buttons on the back of the shirt, and tie into a small knot for some back talk!


And of course… you can always wear your shirt like this!


Check out XX on Facebook for a video showing how Stephanie styled all these looks!


Stephanie Ramlogan

Stephanie Ramlogan is a NYC based Trinidadian Fashion Stylist and Writer, mostly known for her wildly popular blog You can reach her at or check her out at

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