top of page

7 Tips for Transitioning your Wardrobe

Updated: Sep 1

Transitioning your wardrobe can be a huge, expensive, and, oftentimes, emotional undertaking. And while fashion can be a major asset in your gender expression, it can also be a hindrance that creates, or adds to, feelings of gender dysphoria. I talked with a number of local, fashionable queer folks to get some advice on how to approach this challenge. Using their insight and some of my own research, I’ve come up with some tips to get you started on your fashion journey.

Today, we have an absolute wealth of information about fashion at our fingertips. It can be overwhelming trying to figure out where to start. There’s a vast vocabulary to learn on everything from necklines to the types of fabric clothes are made from. On top of that, the options for cuts, styles, and fits are seemingly endless (eg. Silver Bobbin: Modern Fit vs Slim Fit). If you’re someone who didn’t pay a lot of attention to these things until recently, this is a lot to have to learn just to be able to choose an outfit that better showcases the way you want to be perceived.

There are countless articles online about dressing for your body type, skin tone, lifestyle, etc. These can be so helpful to you so long as you aren’t preoccupied with how they’re gendered. Even us queer folks can get hung up on gendering clothes. So, my first tip for transitioning your wardrobe is to ignore the section of the store you’re shopping in.

Tip #1 - Ignore the Advertised Gender of Clothes

There is no reason to gender your jeans; men’s, women’s, it doesn’t matter. Some jeans are meant to make your legs look longer. Some jeans are meant to make people with slim hips look like they have rounder hips or vice versa. Some jeans have larger pockets and thicker material. Some jeans are thin and stretchy. Some jeans have built-in “slimming technology” for those who want more support for soft bellies and thighs. I could go on and on… No matter which side of the store you’re finding your jeans in, what you want to do is find jeans that fit you and make you feel great.

That said, shopping in the “wrong” section of the store or knowing you’re wearing the “wrong” clothing can be a source of dysphoria even when your outfit looks super sharp. So, whatever section of the store you shop in, the important thing to think about when shopping for clothes is the fit and what shape it gives you.

Tip #2 - Cut and Fit Affect Shape

For example, if you have round hips but want a more masculine look, stay away from men’s bottoms that have pleating or pockets that stick out. This will only add more width to your hips. Aaron Ansuini in his YouTube video “FTM & Trans Masc Clothing Tips” also says to stay away from tight elastic waistbands in men’s clothing as they will not only be uncomfortable but will also add emphasis to your hips.

At the most basic, no matter the gender of your clothing, if you want to appear more masculine, you are looking to achieve a blocky or angular shape. If you want to appear more feminine, you will be looking for fits and cuts that emphasize and create curves. There are a lot of cuts made specifically to add weight to certain places or hide weight in others. So, going back to those “dressing for your body-type” articles all over the internet, you can look for tips on how to dress regardless of what you were assigned at birth.

When it comes to creating shape, supportive undergarments can be helpful. If you want it, there are all sorts of padded breast, hip, and butt enhancing underwear available on the market. And, of course, there’s tucking and binding for those who wish. However, make sure you are doing so safely. For example, DIY binding can cause you all sorts of health problems, so investing in a proper binder is important.

With or without the use of supportive undergarments, a good cut or fit of clothing can do wonders for creating the shape or silhouette you’re going for. But, speaking of fit, make sure your clothes fit you.

Tip #3 - Know your Measurements

If you’re trying to dress more masculine, you, like myself, might be tempted to buy oversized clothing. However, drowning in your clothes isn’t actually a good look. Are your shoulder seams halfway down your arm? Do your shorts fall below your knees? Depending on your body shape and size, oversized clothes will likely make you look childish, sloppy, or, if you’re overweight, a lot heavier than you actually are. Simply put, oversized clothes read as you wearing something not meant for you and that is the opposite of what we’re trying to accomplish.

Jackson Bird points this out in his YouTube video “Summer Tips for Trans Guys” where he says you should pay attention to the sleeves of men’s shirts. For slim folks, the wide sleeves of a standard men’s t-shirt can make your arms look even smaller which will give you more of an adolescent look than a masculine one.

For those of you dipping your toes into women’s fashion for the first time, be ready to be exponentially frustrated with clothing sizes. How sizing works changes not only from store to store and brand to brand, but also from cut to cut and fabric to fabric. My best advice to you is to buy yourself a tailor’s measuring tape and figure out your measurements. If you’re shopping for clothes online, most websites have a size chart and some even have images showing how to take your measurements. For further guidance in that area, online sewing tutorials often have great charts for how to take accurate measurements. Rebecca Angela’s Learn-to-Sew: Taking Accurate Body Measurements article is one.

Knowing your measurements can also greatly reduce how many items you have to try on, but you should still expect to try on a lot of pieces before finding a winner.

Tip #4 - Expect To Try On SO MANY Things

It can be really disheartening to try on item after item of clothing that doesn’t fit you how you had hoped. It’s important to remember that you are not a mannequin and an article of clothing not sitting on you how you envisioned is not a failing of your body. It just means that particular piece of clothing isn’t ‘the one’. Clothes are made for people, people are not made for clothes. You don’t need to change yourself for a particular article of clothing.

Until you have a really good sense of what type of clothing works with your body type and what sizes in a particular brand fit you best, expect to be trying on 10-20 different pieces for every 1 that you actually end up buying.

Tip #5 - Invest in Your Basics

When transitioning your wardrobe, it is important to invest in some basic, essential pieces. What this looks like might change from person to person based on gender expression, profession, lifestyle, etc. But the idea is to have some quality, classic pieces that fit you well and that will not go out of style based on the season.

There are plenty of articles online about wardrobe essentials like “How To Create A Capsule Wardrobe for Men” and “The Only 10 Items You Need in Your Wardrobe” for example. These can help you get a sense of the basic items you might want to invest in. These basics are the starting points for any outfit you put together. They can be interchanged, dressed up with fun accessories, or be the neutral part of a new outfit that features that bold shirt you saw at the store and just had to have.

A white or black t-shirt, a classic pair of jeans, a simple but dressy pair of trousers, a casual jacket, a dressier jacket, a pair of casual shoes and a pair of dressier shoes, a nice sweater, a few button-ups or blouses –these are the sorts of basics that you will want to invest in. Once you have them, you can add more ‘exciting’ pieces to your wardrobe over time.

Tip #6 - Pay Attention To What You Like

It sounds like really straightforward advice, but pay attention to what you like whenever and wherever you see it. What’s your favourite colour? What kind of patterns do you like? If you’re new to dressing a certain way, you might not have spent a lot of time thinking about how certain items look or feel on you. And, you might not have any idea what kind of style you want for yourself. When you see something on someone else that you like, compliment them! They might even tell you where they got it. If you try on something in the change room that you just adore, take note of the cut, fit, fabric, colour, pattern, brand, size –whatever it is about it that you love.

If you’re struggling with figuring out what styles you like and want for yourself, Pinterest can be a great asset. Make yourself a fashion board or two on there. Do an image search and save every outfit you see that you like until you start seeing a pattern in your choices. I bet you’ll see a trend in the styles you love real quick!

Tip #7 - Enjoy Yourself

Doing a wardrobe overhaul is a huge undertaking, but it doesn’t have to happen all at once and it will always be an ongoing thing. The styles you choose now don’t have to be set in stone. So don’t get hung up on being precious with your decisions. Your wardrobe will continue to grow and change with you. So enjoy yourself. Get playful. Accessorize. Be different. You are your own unique person who doesn’t let society tell you how your existence should look and your fashion choices can absolutely reflect that.

Recommendations from our community:



299 views0 comments

Recent Posts

See All
bottom of page