My Style Rock Bottom: How I Clawed My Way Back From Stained Sweatpants and Actually Learned Something

I need to tell you about the most embarrassing moment of my adult life, and it happened on a random Wednesday morning about three years ago. I was getting ready for work – well, "getting ready" is generous since I teach from home two days a week now – and I realized I was pulling on the same pair of gray Target sweatpants I'd worn Tuesday. And Monday. Honestly, probably Sunday too. There was this stain on the right leg that could've been peanut butter from my lunch or coffee from my morning cup, but honestly it might've been both because I couldn't remember the last time these things had seen the inside of a washing machine.

Here I am, a guy who literally writes about budget men's style, wearing sweatpants that had lost their drawstring somewhere between the couch cushions, paired with a free t-shirt from some teaching conference that was about two sizes too big because it's all they had left when I finally made it to the vendor table. The irony wasn't lost on me, especially since I'd just finished writing a post about "<a href="https://sartorialhim.com/what-stylish-american-teachers-nurses-construction-workers-actually-wear-to-work/">looking put-together while working from home</a>" the week before.

Jessica walked into the kitchen, took one look at me, and just… sighed. Not mean or anything, just this defeated little sigh that somehow hurt worse than if she'd said something. That's when it hit me – I'd completely let myself go, and I needed to figure out how to get back.

Thing is, I don't think I'm alone in this. Every guy I know has had some version of a style slump, whether it's after kids, job changes, weight fluctuations, or just life getting in the way. For me it was the weird pandemic work-from-home situation combined with some weight gain (thanks, stress eating) and generally feeling like nothing mattered anymore since I wasn't seeing people regularly.

The first step back wasn't buying new clothes or planning some dramatic makeover. It was just… forgiving myself, which sounds cheesy but honestly was the hardest part. My brain kept going "You write about this stuff for a living, what's wrong with you?" But beating myself up just made me want to retreat further into my comfort zone of elastic waistbands and free promotional t-shirts.

I had to remind myself there were actual reasons I'd gotten here. Working from home eliminated most of the external pressure to look decent. Everything was stressful and weird, so comfort seemed way more important than looking good. My normal routines were shot. These weren't excuses, just context that made my sweatpants phase make sense, even if it wasn't sustainable.

Once I stopped the self-flagellation, I could start the actual work of rebuilding. But where do you even begin when literally everything in your closet feels wrong? I developed what I now think of as a three-phase approach, mostly because I'm a teacher and I organize everything into phases whether it needs it or not.

Phase one was the brutal honesty assessment. I tried on everything – and I mean everything – in my closet. Had to admit that yes, I'd gained about fifteen pounds during the pandemic, and no, my old chinos weren't going to fit comfortably again without some lifestyle changes I wasn't ready to commit to yet. About sixty percent of my pre-pandemic wardrobe either didn't fit right or didn't make sense for my new hybrid work situation.

But that remaining forty percent? That gave me something to work with. A few pairs of jeans that still fit okay, some t-shirts that weren't completely shapeless, a couple button-downs that worked for video calls. Not exciting, but enough to put together actual outfits while I figured out next steps.

Phase two was what I called the strategic reset – basically filling the most critical gaps so getting dressed didn't feel like a daily crisis. I spent maybe $200 total at Target and Old Navy getting basics that actually fit my current body. New jeans in a slightly more relaxed cut (okay, fine, I went up a size), a few well-fitting t-shirts, two casual button-downs, and one decent pair of chinos for when I had to look more professional.

The psychological impact of just having clothes that fit properly was honestly shocking. I stopped dreading getting dressed in the morning. Started leaving the house more. Even felt confident enough to turn my camera on during Zoom faculty meetings, which I'd been avoiding for months.

Phase three was the longer-term rebuild – gradually figuring out what my style should look like based on who I am now, not who I was before. I actually made a little document (yeah, I know, peak teacher nerd behavior) with three questions: What parts of my old style still feel like me? What does my current lifestyle actually require? What's one small thing that always makes me feel more put-together?

For me, those answers were: I still like layered looks and interesting textures; I need clothes that work for both home office days and actual school days; and wearing decent socks instead of whatever white tube socks I grabbed from the drawer always makes me feel more intentional, even if nobody sees them.

This framework helped me make smarter purchases over the next few months instead of panic-buying a whole new wardrobe that might not actually work for my life. I picked up a couple of flannels for layering, invested in some better quality t-shirts, got a few pairs of interesting socks that made me smile.

Throughout this whole process, I learned some practical tricks that made everything easier. First, I started with underwear and loungewear – sounds backwards, but having underwear that actually fit and loungewear that didn't look like I'd given up on life completely made me feel more human, even when I was the only one who knew the difference.

I also developed a "uniform" formula that I could fall back on when my brain wasn't working: flannel or button-down plus jeans plus my desert boots. Not revolutionary, but it works for my body and lifestyle, and knowing I have this reliable combination takes the stress out of getting dressed on rough mornings.

The "rule of three" became my friend too – adding a third piece beyond pants and shirt instantly makes any outfit look more intentional. A light jacket, an overshirt, even just rolling up sleeves or adding a watch. Small changes that make a big difference.

One thing that really helped was finding other guys online who had similar body types and weren't afraid to show how they dressed. Seeing teachers and other regular guys with dad bods putting together decent outfits reminded me that looking good isn't reserved for people with perfect bodies and unlimited budgets.

I also set a realistic budget – about $50 a month that I could spend on rebuilding my wardrobe without Jessica giving me the look. Having that boundary actually made me more thoughtful about purchases instead of impulse buying stuff I'd regret.

The biggest lesson though? This whole process takes time, and that's okay. Rebuilding your style after letting it slide isn't just about buying new clothes – it's about rebuilding the habit of caring about how you present yourself. That mental shift doesn't happen overnight.

Three years later, my style is different than it was before my sweatpants phase, but it's not worse – just adapted to my current reality. More comfortable but still intentional. More practical but still distinctly mine. And importantly, it accounts for the fact that my weight fluctuates a bit, like most normal humans.

The most important thing I learned wasn't about specific clothes or brands, but about maintaining an ongoing conversation with myself about how I want to show up in the world. When I stop thinking about it entirely – when I just grab whatever's closest and cleanest – that's when I start sliding back toward stained sweatpants territory.

So if you're coming out of your own style wilderness period, whether it lasted weeks or years, just know you're not alone. Getting back doesn't require some dramatic transformation or spending a fortune – just honest assessment, strategic basics shopping, and patience with yourself as you rebuild both your wardrobe and the habit of caring about it.

And maybe, just maybe, actually doing laundry more than once a month. Jessica's still working on me with that one.