Let me take you back to the worst fashion fail of my adult life. Picture the scene: it’s just an ordinary Wednesday morning, about three years ago. I’m getting ready to go to work.
Okay, fine, “getting ready” may be an overstatement – I currently teach remotely two days a week, so I don’t “get ready” to go into the office. But I am getting dressed. And as I was pulling on a pair of grey Target sweatpants, it hit me that these were the exact same sweatpants I wore yesterday.
Tuesday. And probably Monday.
To be honest, I may have even worn them Sunday.
There was a stain on the right leg, which was possibly peanut butter from my sandwich or coffee from my morning mug. But to be honest, it was likely both – because when did these sweatpants ever make it inside a washing machine again? I was a dude who writes about affordable menswear looking at a pair of sweatpants with no visible means of fastening around the waist that were hanging on my body by a thread…literally.
I think my shirt may have been leaking through the sweatpants too. It was one of those free t-shirts you get at conferences that isn’t even your size because they were totally sold out of yours at the teacher teach convention vendor table and THAT was the only thing they had left by the time you realised you needed clothing to work at this teaching conference. Oh, and the sad part?
I finished writing a blog post about “ how to look put together while working from home ” just one week prior. Fast forward to Jessica walking into the kitchen, seeing me in my comfy clothes charade, and sighing. Not an angry sigh.
More of a sigh of defeat. You know the one I mean. The one that kills you more than if she would’ve just yelled at you.
That sigh. There it was. Official confirmation I had completely fallen off the map and needed to chart a course back.
I don’t know about you, but I feel like every guy has gone through some sort of style dry spell or sartorial setback at some point. Maybe after having kids you just stopped caring. Maybe you had a job change and got stuck in company polo shirts for years.
Maybe you lost or gained a bunch of weight and fell out of love with your closet. Mine happened to stem from working from home in a not-normal capacity (aka pandemic life) and gaining a few poundslette because of delicious panic eating, aka chips. On top of that, I think I just felt weird wearing trousers since nobody was around to see me in them on a daily basis.
Phase one in my recovery wasn’t rushing out to buy new clothes (although I’d be lying if I said that wasn’t the finish line I was looking forward to). Phase one was simply forgiving myself. Easier said than done, of course. “You know how to DO fashion?
You’re the one who writes about this stuff!” Trust me, I told myself the same thing. Guilt will only discourage you from wanting to try harder, though. Nothing motivates me to crawl back into my fluffy cocoon of baggy jeans and holey tees quite like guilt.
I needed to remember that there was method to my clothing madness. Sure, working from home meant I didn’t have to dress to anyone’s standards but my own. Life was stressful.
Pandemic weird. Everything was just chaos. Who cares if I wore trousers?
What made matters worse was my normal routine was thrown out the window. Again, not excuses. But rather explanations to why I got to a place where wearing Target sweatpants to stand for class was acceptable.
Once I let go of beating myself up about my wardrobe choices (or lack thereof), I could start to clean up my act. Literally. But before I could start buying new clothes to refresh my wardrobe, I had to answer the hard questions.
Like, where the hell do I start? When everything in your closet feels wrong, how do you turn it around? Well, if you’re anything like me, you develop a three-phase process to recovery.
I’m a teacher remember? We love hierarchical learning structures. It’s how we’re wired.
Let’s dive into phase one: the brutal self-assessment. If you recall from my confession above, I gained weight during the pandemic. About fifteen pounds, to be exact.
My closet wasn’t entirely filled with loose-fitting slobs. But…and this is a big but…many of my “dresser” clothes didn’t fit me quite right anymore. I dug through my closet and did the honest work of trying on everything.
I’m talking tops, bottoms, shoes, you name it. What was left in that poor closet really made me take stock of where I was at that moment in my recovery. I’d say around 60% of my pre-quarantine wardrobe was either too small (hellooo tight jeans fail memories) or didn’t make sense for my “new normal” working routine.
Did I mention that about 60% of my wardrobe didn’t work for my post-pandemic life. But that still left 40% that I could work with! A good chunk of my jeans still fit.
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I had some tee shirts that weren’t entirely shapeless. I even had some button-ups that I could probably wear Zoom sessions with. It wasn’t ideal, but it was enough.
Enough to give me some outfits that I wasn’t embarrassed to wear and enough inspiration to start seeking out new staples to add to my wardrobe. Phase two was what I like to call the strategic reset . Not quite Marie Kondo-ing your wardrobe but filling in the biggest gaps to get you to a place where dressing didn’t feel like a crisis every morning.
I went through and probably spent about $200 total at Target and Old Navy getting fitted for some basics that actually fit my body. I got a few pairs of jeans in a more forgiving cut (okay yes, I went up a trousers size), some fitted tee shirts, 2-3 casual button ups, and a pair of chinos I could wear if I needed to look more “business casual.” I can’t even tell you how good it felt to once again have clothes that fit. I wasn’t excited to get dressed in the morning.
Okay yes I was because I love clothes…but I also started leaving the house regularly again! I even turned my camera on for my Zoom school faculty meetings. Something I hadn’t done in forever because of my fatigue l clothed bod.
Phase three came when I actually started thinking about how I wanted my style to be moving forward. Once I felt comfortable enough in my own clothes and had some basics that fit my post-quarantine body, I was ready to tackle my style woes with fresh eyes. I literally made a document (yes, I am that teacher nerdy) and wrote out 3 questions.
Question 1: What still feels like my style? Question 2: What do I actually need for my lifestyle right now? Question 3: What’s 1 small thing I can do to feel more put together?
For me… – I still love a layered look with some personality when it came to textures. – I needed clothes that could work for at home days and in person school days. – Wearing socks that match my outfit rather than just throwing on grey or white tube socks every day is one small change that helped me feel more “put together.” Getting the hard questions out of the way let me really focus on what I needed moving forward. Instead of making panic purchases just to feel like I had a full wardrobe again, I bought pieces I knew I would wear. I picked up a couple flannels for layering.
Some nicer t-shirts. A few pairs of fun socks to make me smile. Now that we’ve covered the 3 phases of my recovery, let me fill you in on some tactics that helped me along the way… Start with your undergarments and workout clothes.
Okay, hear me out. I know that sounds backward but starting with stuff you’ll only wear at home helped me feel “human” again. Getting into some underwear that fit properly and workout clothes that didn’t look like a rejected sorority party outfit from the ’90s went a long way for me.
Pick a formula for your “uniform.” Trust me I get it. You’re not Steve Jobs. You don’t need one standard outfit you wear everyday.
But having some sort of formula you can roll with when you’re having an off day is clutch. That formula for me was either a flannel or button up + jeans + my desert boots . Boom.
Done. Add a third piece. Speaking of layered looks, adding something in addition to your shirt and trousers is an easy way to feel put together.
Grab a light jacket, wear an overshirt, roll up your sleeves. Any little accessory that helps you feel good is a win in my book. Find guy-in-real-life fashion accounts you relate to.
This may sound weird but when I was looking for fashion inspo I made sure to search for guys that kinda looked like me! Bonus points if they were teachers like me. I found so many dudes with actual lives (read: kids) that were putting together awesome outfits and making it look easy.
It helped knowing that “normal” people with dad bods could pull off cool outfits. Give yourself a budget. Whether it’s $25, $50, $100, or more per month, give yourself some guidelines on how much you can spend getting back into the wardrobe saddle.
This isn’t a free for all! And trust me, setting a budget will help you be more intentional about what you’re buying. Pro tip: tell your wife or husband your budget and you’re more likely to stick to it!
Remember it takes time. Rebuilding your wardrobe and your style takes patience. Don’t rush out and buy every shirt, pair of trousers, and funky sock you see at the store.
Fashion is a journey my friends. It’s okay to take your time. It’s been three years since I wore sweatpants as trousers and I’m actually happy to say that I’ve built on my wardrobe from before quarantine.
Sure, my style has changed since “falling off” the menswear wagon but that’s just natural progression.
My style is more comfortable than it used to be. More me.
And most importantly, my clothing doesn’t pinch or pull when I wear it since I made sure to build my wardrobe back up around my current body – not the body I forgot I had lol. If there’s one thing I really took away from my journey back to stylish Menswear without breaking the bank? Don’t wait for fashion “ emergencies ” to pop up.
Be proactive in having conversations with yourself about how you want to feel when you dress. The second you stop paying attention is when you’ll find yourself back in a clothing rut. Trust me, I wear jeans and a fancy shirt almost every single day.
But on days when I don’t feel like thinking about outfits, I’ve caught myself just grabbing whatever and hoping for the best. And that, friends, is how you slip back into sweatpants… …consider wearing trousers tomorrow. Jessica still doesn’t let me forget about that laundry situation.
