Trickiness of transitioning: replacing my wardrobe

By: Samuel Smith, Contributing Writer 

Views expressed in opinion columns are the author’s own.

One of the trickiest parts of my transition has been trying to figure out what to wear. I came out as transgender and started testosterone relatively young, at 16 and 18 respectively. However, that still meant I was 16 years behind my peers. I came out with a closet full of dresses and skirts, and at first, my outfits of choice were whatever male clothes I could thrift. Trying to transition your wardrobe can be rough, confusing and intimidating at times. I’m now 21-years-old, and through many years of trial and error, I have a pretty good grasp on men’s fashion, and I have compiled some tips.

First, and most importantly, wear what you want. You can be a man and rock whatever you want. Whether that’s a Pokemon t-shirt, a dress, or a suit, a large part of transitioning is finding what makes you comfortable and showing your confidence. It’s also important to note that fashion is starting to blur the line between the binary genders. More men are wearing skirts, and more women are wearing suits. However, there are still some tricks you can use if you’re going for a more masculine look, rather than feminine or androgynous.

Before getting started, think about what kind of aesthetic you want. What kinds of pieces do you envision yourself wearing? Pinterest is a really good place to find various styles. It’s also okay if this changes over time, or you’re not quite sure. When I started my transition, I was more into punk and grunge. It was pretty effortless, but at the same time, I could DIY certain clothes by adding patches and pins. 

Nowadays, I go for a more tailored look, I like sweaters and button-ups, and I wear my brown Chelsea boots almost every time I go out. It’s also important to think about color palettes. When I started off, I wore a lot of black and not much color. Now, I wear a lot of blues, greys, and browns. Finding out what colors go best together is important as well, having an idea of color coordination can help in picking out clothes that actually go together.

Shapes are pretty important in fashion, but they’re going out of vogue. A basic rule of thumb is that “typical” men’s fashion is straighter lines, visually more squares and rectangles, while women’s fashion is rounder and softer. I like to play with shapes. I’m pretty short and round, so finding ways to straighten my silhouette is helpful. When I wear shirts, I like to have a sweater, flannel, or jacket over them to straighten out lines and add a little bit of texture. At the same time, I like big sweaters, which do end up looking somewhat softer. Feel free to play with lines and shapes, potentially layering different pieces to get the style you’re looking for.

Pants are always a struggle for me. My quads are pretty big and I’m relatively short. Pants that fit in the quads may be loose in the calves or waist, and pants are always too long for me. Because of this, I end up wearing a fair amount of jeans. I cuff the ends of my jeans, which I find straightens the silhouette of my leg and makes me look taller. Sometimes, jeans are significantly longer than normal or I buy more formal pants that won’t cuff. Those, I take to my local tailor. It isn’t that expensive to get a couple of pairs tailored here and there, and I’ll always ask for them to sew a cuff into the ends. If you can afford it, a tailor can be a game-changer in how clothes fit.

Lastly, I love to play with patterns. When I started my transition, I wore relatively simple clothes. However, because gender roles in fashion are blurring together, I can throw in things I wouldn’t normally wear. I especially like wearing patterned button-ups. Not only do they add a fun little flair to my outfit, but I also find busy patterns can make my chest look flatter. My chest is a big source of dysphoria for me, but fun patterns, plus a little layering, can help distract. Patterns can also just be fun and make me feel more confident! Again, confidence is key in styling your wardrobe. You’re paying for these clothes, you should at least enjoy wearing them!

Fashion can be really tricky. I’m still figuring out my wardrobe and what I like to wear. I think fashion is a journey you’ll be on your entire life, as you age and your personality changes so will your wardrobe. But I also know from experience that transitioning from one gender to another can be especially intimidating as there are totally new rules involved. That being said, I think the biggest tip is to wear what makes you feel the most comfortable and confident.

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