For as long as I've had friends, I've had friends who are more fashionable than me. It's not hard. But in 2015, one of my very most fashionable friends decided to start a blog/zine about nerdy fashion and related topics and asked if I was interested in contributing.
I may not be fashionable, but I sure know how to talk.
I ended up doing two "columns" total and I figured I might as well share them here. I also did a "lookbook" or two that I might revamp.
Growing up I was not a big fan of clothes.
I wasn't a nudist, no. I thought of myself as a tomboy and violently allergic to what my classmates were wearing. In middle school that meant I wore long, flowy skirts with jeans underneath. In high school that meant a goth-grunge hybrid wardrobe full of black t-shirts, flannel and ratty jeans. I was teased for it, but that's high school, and it only served to make me more resolved not to give a damn what I "should" be wearing.
As it turns out, I'm wearing flannel, ratty jeans and a grey t-shirt right now. The t-shirts have rotated since college, but what I am comfortable in has stayed largely the same since then. I have sensory issues that mean I'm very picky about the materials that sit on my skin - I like soft, I like loose, I like certain textures and not others. I'm a bigger guy to start with so that translates into difficulty finding things that fit properly, another reason I tend not to think too much about what I'm wearing. (Aside from my shoe collecting habits, but that's a blog post unto itself, really.)
That's not to say I don't think about what other people are wearing. Conceptually, I really enjoy fashion. I like looking at new collections and have favorite designers. I like Project Runway. I have Pinterest boards for things I like the idea of wearing: menswear, steampunk, post-apocalyptic raver gear. If I was braver, and happier with how I look, I think I would be more adventurous.
I am in the process of becoming happier with how I look. Because I am a transgender man, because I'm fat and muscular and a long way from the kind of trans guys who are held up as looking good, it's been a longer and more complicated process than it is for some people. I have spent a lot of time trying very hard not to think about how I look. I try clothes on without looking in mirrors. I wear t-shirts until they're not fit to be seen in public, and then I search out near-identical ones.
My "office job" clothes were always femme-passing, because I felt unprofessional wearing things that didn't fit well. When I quit my previous job, I donated all of my feminine clothing in one fell swoop, never to be faced with it again. I'm currently considering re-entering the workforce presenting as a man, and that means rebuilding a professional wardrobe. I am really thinking about how my clothes look on me, and for the first time in my life, sometimes I can look at myself in those clothes and say "yes. Yes, that's me."
It's intoxicating, and it makes me want to see how far I will be able to take this over the next few months and years, as surgery, hormones and strength training all (hopefully) leave their mark on my body.
Most of my wardrobe has come from thrift stores since I was a teenager. Having shopped for both masculine and feminine clothing, I have amassed a series of tricks that I use to get in and out faster and encounter less disappointment when I'm shopping secondhand. Thrifting is always half luck and half even more luck, but when you're looking for larger sizes it becomes a real challenge instead of a fun scavenger hunt.
The most important thing you can do for your self-esteem is to know the selection at your local stores. There's nothing more discouraging than finding absolutely nothing in your size, or in any size close to yours. To reduce the likelihood of that outcome, I make it a priority to know which of my local thrift stores carry and shelve clothing in my size, and how they put them out. For example, Goodwills in my area have plus-sized women's clothing in a special section, usually off in a corner by the pajamas. If you don't know where you should be looking and you try browsing the racks for a shirt, you're going to be disappointed regardless of how many Goodwills you shop at.
Making a beeline for the plus section means you don't see that great top that doesn't fit you, which helps by cutting down on negative self-talk as well. It also helps to know what stores to skip entirely - the same nearby Goodwills that have a section for plus-sized women just don't have any plus-sized men's clothing. If I know their jeans are going to stop at a 44 waist, then I know not to bother shopping there if I need jeans.
If you live in or near a decently sized city, it's worth checking to see if there are any resale shops near you that specialize in plus-sizes. These will usually be consignment stores and a little more expensive than your usual thrift, but if you're looking for something special (or professional clothes in general) it's good to know you have a more guaranteed option.
Scope out your options in advance, so that when you need something, you know where to start. The advantage of looking ahead of time is that you can do it when you're in a positive headspace. Wandering through fifteen thrift stores that don't carry your size when you're already feeling terrible about yourself is an exercise in self-hatred. If you know what your best options are going to be, whether it's the Value Village or the consignment store downtown, you'll be able to cut down on the unpleasant parts of shopping and spend your time on the fun, encouraging part, where hopefully you find great-looking clothes that fit.