I’m here to confess to you the low point of my sartorial existence. Three years ago, on a nondescript Wednesday morning, I woke up to go to work and realized I was wearing the same pair of gray Target sweatpants I’d worn the day before. Oh yeah, and the day before that too.
Probably the day before that. There was a suspicious stain on the right pant leg that was likely caused by peanut butter from lunch or coffee from breakfast. Or both.
I couldn’t really remember when these sweatpants had last seen the inside of a washing machine. It was then that I knew I had a problem.
You see, I’m a menswear writer.
A guy who literally publishes photos of himself and writes about how he dresses on the internet. And yet here I was teaching my college students via Zoom in old sweatpants with no drawstring and a complimentary t-shirt from National Conference of Teachers of English that was at least two sizes too large because… well, they were “out of size smalls” when I finally got to the booth. I’d even written a blog post the previous week called “ How to Look Put Together While Working from Home” No irony there at all.
When my wife Jessica walked into the kitchen that morning she gave me a look of silent judgment. You know the look. Not even a nasty look, just a sad little sigh of disappointment that actually cut deeper than if she’d said something rude to me.
It was then that I realized I had completely fallen off the face of style, and I needed to find my way back. Trust me, I don’t think I’m the only one who’s ever gone through a style crisis like this. We all have something in our lives that triggers a lapse in how we take care of ourselves.
Kids, job changes, losing or gaining weight – life happens. For me it was working from home during a global pandemic mixed with gaining a few pounds (damn you stress eating) and generally lacking motivation to care what I looked like when I wasn’t seeing friends or colleagues in person on a regular basis. The first step to getting back into casual style shape wasn’t shopping.
Hell, it wasn’t even thinking about shopping. It was just forgiving myself. Yeah, sounds stupidly simple and straightforward, but trust me it was the most difficult step for me.
Part of my brain kept screaming “You know STYLE FOR LESS. You’re the mans contribution to menswear media WHAT’S WRONG WITH YOU?” Well, whenever I started thinking like that I found myself going deeper into comfort clothes hole I was digging myself out of. Once I quit beating myself up I was able to really think about how I got here.
Again, it’s likely not that different from most of you. Working from home means you don’t face the same social pressures to look nice on a daily basis. Life in general was so stressful and abnormal during the pandemic that comfortable wins almost every time over “put together.” Suddenly all my routines and rituals I had for getting ready were thrown out the window.
And let’s be honest, they were ALSO excuses. Rationalization even. But excuses none-the-less.
What’s the saying about prisons? Once you’ve built yours, you’re screwed until someone helps you escape? Yeah, that.
So I forgave myself for falling into a rut and started figuring out how to climb out. What are the first steps to take when YOU look in your closet and feel like nothing looks good on you? Well for me, and probably for you it all starts with clothes.
If you’re looking at your wardrobe and everything feels off it can be really tough to know where to start. I have a tendency to break just about everything down into “learning units” because I’m a teacher. Bear with me kids, I’ll try to keep the education metaphors to myself from here on out.
Phase 1: Acceptance. I started by simply taking stock of what I had. Literally every article of clothing in my closet got pulled out and tried on.
Some sad truths came to light when I did this. Turns out I had gained almost fifteen pounds over the course of the pandemic and my old “dress” pants weren’t going to magically fit me again any time soon. Close to 60% of my pre-pandemic wardrobe was either too small OR didn’t make sense for me working from home part of the week.
What did that leave me with? Well surprisingly enough, about 40% of my clothes were still good! Not sure what I was going to wear every day yet, but I definitely had the basics to put together some outfits as I figured out my next move.
Phase 2 was where I started to address my biggest clothing needs. Could I really get by with just shirts and pants? Nope.
Jackets? Scarves? Accessories?
Obviously. But if I had to boil it down to just a few categories of clothes that I needed to fill the gaps it was underwear, jeans, t-shirts, casual button-ups, and work pants. I probably spent around $200 dollars total at Target and Old Navy stocking back up on the basics that actually fit my body.
You Might Also Like
I bought new jeans – literally the last pair before this whole debacle I weighed about 15 pounds less so I went up a size and got a slighter more relaxed fit. Same for my t-shirts. Some fresh button-ups that actually fit again, and a new pair of chinos I could wear if I had to look more “business casual.” I honestly cannot stress enough how awesome it felt to know I had underwear that fit again and t-shirts that didn’t look like parachutes.
Suddenly getting dressed didn’t feel like a panicked morning decision anymore. I started leaving the house regularly again. Best of all?
I turned my camera on for my next Zoom faculty meeting. I hadn’t done that in MONTHS because I hated how I looked. Feeling confident enough to do that small thing made me realize how far away I had let myself get.
Phase 3 for me was taking a long hard look at what my style should be moving forward. Since I knew I’d probably never fully return to pre-pandemic life I wanted to make sure I stayed true to myself but didn’t just blindly revert back to my old style. So I made myself a lil spreadsheet (I’m a teacher remember?) and asked myself three questions: What still feels like me?
What do I NEED clothing-wise for my lifestyle? What’s one small thing that can make me feel more put together? For me the answers looked something like this: I still love having layers and fun textures My life still requires clothes that look good in person and on Zoom.
Wearing non-white socks is one easy way to feel more intentional. This helped me figure out how to prioritize what I SHOULD buy moving forward instead of just trying to replace my whole wardrobe with clothing that didn’t really suit my lifestyle. I picked up a couple flannels for layering.
Some nicer t-shirts. A few pair of fun socks that I actually smiled when I put on. Ok guys, so once I identified these core needs there were a few simple tricks that really helped me along the way, both with shopping and with just getting dressed in the morning.
First, underwear. Don’t sleep in your work pants from the day before. Trust me, that linen shirt you wore to work Fridays just doesn’t look the same when it’s your pajamas too.
Honestly start here. Get good fitting underwear. Comfy pants you actually LIKE to lounge around the house in.
Feeling messy starts from the waist down folks. I also started getting into what I call “uniforms” to simplify thinking about clothes in the morning. Once I identified what WAS working for me I could boil most of my outfits down to formula that I could replicate.
For me that formula was either a flannel or a button-up shirt + jeans + my desert boots. Not sexy? Probably.
But it fits my lifestyle and my body. Knowing I can throw those things together and know it’ll look OK makes getting dressed easy. The “rule of three” is another trick I fell in love with.
Any outfit can look more intentional by adding a third piece. Beyond shirt and pants add a light jacket, an overshirt, heck even just rolling up your sleeves or wearing a watch. Little touches that don’t take much thought but improve any outfit.
Finally, I started looking at other dudes who had blogs and wore clothes I liked that weren’t super slim or “photoshop skinny.” Reading guys like Trevor Russo, Parker Bowie, Tailored fit Ryan, Ali Vezzara, Marc Lonergan, and Alon Levy always reminds me that there are normal guys out there with REAL body types wearing clothes I like. If they can look good, I can too. Look, shopping for clothes can be expensive.
But you don’t need 20 pairs of jeans to recover from your own style rut. When I got back into shopping I set a budget for myself of $50 / month that I could spend on clothes. That way I wasn’t panic buying everything in my closet at once AND Jessica wasn’t giving me the evil eye whenever we passed her closet.
The biggest thing I took away from all of this is that rushing the process doesn’t help. Rebuilding yourself after a period of time where you didn’t care about your appearance takes time, and that’s ok. Take those three steps I talked about.
Really evaluate what you HAVE. Then fill in your gaps, and build from there. Don’t worry about being trendy or “grammable.” Just wear clothes that fit and make you feel good.
Three years later I don’t dress exactly how I did before my sweatpants phase, but that’s ok.
In fact I dress much better than before. Comfortable, but still put together.
Practical for my life but still holds hints of my personal style. Most importantly it’s adaptable. I’ve learned to accept that my weight will ebb and flow a little bit like most humans and that’s perfectly fine.
Am I done evolving my style? Absolutely not. The important thing is that I’m ALWAYS thinking about how I want to present myself to the world.
As soon as I let that care go – as soon as I start throwing on whatever shirt and sweatpants are closest to me when I wake up – is when I start sliding back down the slippery slope to wherever it was my style wandered off to. Learn from my mistake, and don’t forget to do laundry regularly. Jessica’s still working on me there.
