Positive Masculinity Contributor – Maxwell Hayden
Content Writer | Politics, Philosophy & Economics Student
I spent the first eighteen years of my life on complete outfit autopilot. When your wardrobe consists mainly of basketball shorts, jeans, sweatpants and graphic tees, getting dressed in the dark every morning becomes the standard affair. Being able to wear the same handful of outfits most of the time is one of the silent advantages that male-passing folks have over everyone else. Taking your clothing for granted means missing out on opportunities to grow intrinsically and extrinsically. When you’re not making decisions about the way that you dress, you’re letting the world around you come to their own conclusions. Dress right, and you’ll be building an identity for yourself and developing self-confidence at the same time. In a world where it’s becoming much more common to knock yourself down, looking good is an accessible means of lifting yourself up.
That said, nothing with so much potential for good comes easily. Trying to discern your style is a difficult enough process as it is; add to that the fact that many men feel the world of fashion is closed off to them, and the goal of looking good becomes all the more difficult to achieve. But I can attest firsthand to the fact that it’s doable, whether you’re skeptical of the impact clothing can have, or are struggling with body image insecurities, or can’t tell a v-neck from a crew. I hope that by outlining a few of the first steps that I took to clear out my t-shirt drawer, you’ll find a useful takeaway or two, whether that’s following my formula step-for-step or merely gleaning the inspiration to dig deeper on your own.
The Journey of a Thousand Miles
The first hurdle I had to leap while learning how to dress myself was the most difficult: discovering that I could look good in the first place. As someone who is overweight and not visibly muscular, I hated clothes shopping with all my heart. I felt silly looking at the clothing models and mannequins pulling off looks better than I ever thought I could, and given the pricey nature of most nice clothes, I couldn’t justify just trying something for the sake of trying it. I would often walk out dejected, empty-handed, and ready to put off trying again until I could lick my mental wounds.
If any part of this resonates with you, I’d advise starting by taking yourself out of the equation. I was fortunate enough to stumble into this trick by accident, via a Christmas gift from my mom. She set me up with a service called StitchFix, which is designed to provide you with an outfit or two based on your body type and any additional requests you have. If you don’t like them, you can try again until you do. Should you have the financial luxury to give a service like this a shot, I would; having a starting point tailored to your needs (or a lack therof) does a lot to remove insecurity from the equation. After all, you’ve already received the approval of at least one person who knows their stuff!
You can simulate a similar experience for yourself on a budget, too. Ask someone close to you—a partner, a family member or a friend—to go to a store in your financial range and pick out a top and bottom for you that they think would be flattering. That way, you have someone already invested in your success, perhaps even more than you are, to keep you accountable in the moments when it all gets too overwhelming. Plus, you might not know any fashion pros, but you do know someone who knows you, and can pick something out that suits your personality in a way a stranger can’t. The goal here is to get your hands on a single piece of clothing that you like and go from there.
Once you have secured something that you enjoy wearing, the process starts to get easier, because you’re no longer painting on a blank canvas—it becomes more like working on a coloring book. The article of clothing (in my case, a sweater) serves as the outline, and you can start pairing it as you please. Stick to what you already own at first. Does this sweater look good with your darker jeans? What about khakis? Don’t play the comparison game between looks yet; just evaluate whether or not you’d like to wear them out. You’ll start to get an initial feel for what colors you’re into, or looks that might work better in certain situations than others. In the best case, you might even already have a specific new wardrobe addition in mind! When I next walked into a nearby Men’s Warehouse, it struck me just how much easier it is to shop for clothes when you know what you’re looking for, or at least a rough approximation of it. Once you feel confident enough to nab your next pair of pants, rinse and repeat using those as your new base. Eventually, you’ll not only have a swath of fun individual options to mix and match, but because you bought all of your clothes with a specific partner article in mind, you’ll always have combos to lean on in a pinch!
I made my closet transformation over the summer before my junior year, starting with that simple green sweater and gradually working my way all the way up to accessorizing with jackets and jewelry! It was a feat I would never have thought possible even a year before. When I stepped foot back on campus in the fall, the response to my efforts caught me completely off guard. From the small ways that people’s glances at me changed, to the compliments I received from friends and strangers alike, I felt all the work had been worthwhile. But, truth be told, that validation came long before I ever encountered anyone else. My newfound identity was a much-needed boon coming out of the pandemic, and the confidence that followed allowed me to carry myself with more poise (which was potentially even more socially potent than the clothes themselves!). Whether you want to dress in traditionally masculine fashion, or find your groove with feminine pieces in the mix, you’ll be doing yourself a service to give those impulses a shot.
And, while you’re at it, consider paying a compliment to other men you see trying something new! Masculine circles aren’t often considerate enough of bold fashion decisions, and your small show of intimacy may be just what a buddy needs to keep developing their style.