As WordPress continues to recycle old prompts, I pulled another prompt from The Coffee Monsterz Co to respond to today
How have your clothing and fashion choices changed over the years?
As someone born in the 70s, grew up in the 80s, came of age in the early 90s and is living 50 year old man in 2025, I like to think that my clothing and fashion choices have changed with the times over the decades. At least up to a point I think they did.
I read somewhere once, I can’t remember where, but somebody said, as we become adults, we basically find a decade that we like, fashionably speaking and pretty much spend the rest of our lives, living there. If that’s true, then I can stay with some serenity that I basically fell in love with the fashions of the mid-1990s and I’ve pretty much stayed there ever since.
I think that early to mid 1990s and the L2 brief “grunge movement“ brought back to you some simpler, more timeless fashion trends. This is my way of saying that I am basically a T-shirt and jeans guy. I always have been, and most likely always will be
I hate wearing long sleeves. I feel so bunched up in them. I was telling one of my coworkers when I went into my billing yesterday that Bill will never see me wear a long sleeves. Maybe if I’m wearing a certain tie, but that’s about it.
I wonder sometimes whether or not I “dress my age” at this point, I really don’t care. Don’t get me wrong, I’ve gotten out of the age where the T-shirts with pictures on them are really sarcastic text Adam. But short sleeves and a crewneck or just uncomfortable in.
I don’t mind khakis or even dress pants, but for me, the more simple the better. As far as my feet are concerned, tennis shoes are my footwear of choice. However, I will wear dress shoes when it’s appropriate to do so.
I guess I love this is really an extended way of me saying that I place value on comfort over aesthetic when it comes to my fashion sense.
A fashion swing and miss
A few years back, when I was still dating, Jessica, we went to go shopping for me one day. I think I was going to pick up a pair of pants for work. And then turning into a situation where I bought those pants and she ended up Buying me a couple shirts and a couple pairs of jeans. She clean that she really liked the “skinny jeans“ look. She wanted to buy them for me. I obliged her; because I really wanted them, but because she did. I might have worn them once one time when we got together. If that.
Once we broke up, those skinny jeans were promptly donated. I probably could’ve sold them on Facebook marketplace. But I just wanted them gone. Part of it was because they were a reminder of her. Part of it was because I knew that I would never wear them. Another part of it was because I was frankly embarrassed that I became “that guy“ who ended up letting my then-girlfriend pick out my clothing. But that’s the kind of dumb stuff that we do and we think we’re in love and we’re just in a relationship.
The truth is, skinny jeans are the stuff of my son‘s generation. They’re not meant for me and quite frankly, I was never comfortable in them. Having said that, I’m not ready for a “dad jeans“ yet 
Meanwhile
As for me, today, I’m kind of under something of a time crunch. The kid was with me most of the week and while I briefly got to my classroom room and got started setting up, I basically have to get everything else completed today on Saturday. We’re having a staff meeting at my school on Monday, with the school year beginning on Tuesday.
As I’ll be moving kid one into his college dorm on Monday, I will not be there for the meetings. As a precaution, I went ahead and arrange for a substitute teacher for the first day of school. But even before, then I’m going to a baseball game with Veronica this evening.
Tomorrow morning I will be getting on the road to Madison. Before I get there, however I’m going to make a little stop in Milwaukee to catch up Brewers game. That’s mostly to make up for the game that I missed in April. But let’s face it, even if I had gone to the game in April, I probably would be going back for this trip tomorrow as well. Needless to say, I will be posting about both my experience moving Kid 1 into college and my ballpark review of Milwaukee within the coming days 
Thanks for stopping by Rebuilding Rob. Be sure to like, 👍 comment and subscribe to my blog below. It’s greatly appreciated! Also, feel free to follow me on social media as well! Check out my most recent posts as well as some earlier, related (and perhaps, not-so-related) posts:
- Rob’s Retro Movie Review: This is Spinal Tap (1984) – The Movie That Scaled to Eleven
- A Death in the Family (And My Disposable Income): My Life in Comics
- The Supporting Cast: Navigating the Eras of Male Friendship
- Life is What Happens: A Look Back at My Non-Existent 2025 Vision
- The Moment I Walked Inside a Hallmark Movie
The article “sticking to the basics” first appeared on Rebuilding Rob.
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