Middle-aged man earns right to dress himself – for now

My wife hates the way I dress. The shirts and ties I wear to work are okay (just okay, nothing fantastic), but the clothes I wear in more casual circumstances will not do. The shade of my blue jeans is not right; I wear my shirt tucked in when all the hip older gentlemen are leaving theirs out; and having pants that fit just right is no excuse not to wear a belt. I didn’t know this, but holding your britches up is only one of the reasons to wear a belt, and probably not the primary one.

I’m a country boy, and I dress like it. I wear clothes to be clothed. Warmth, comfort, and hiding my shame are my concerns when it comes to wardrobe. I developed a dislike for clothes shopping early in life and have honored that dislike to this very day, which is why I tend to wear an article until it is no longer comfortable or has quit hiding the more disturbing views of my shame.

I grew up being told to tuck in my shirt. That was how you made yourself look respectable. After many years, I finally learned to do this routinely and figured I was set, as far as managing the transition between shirt and pants. I was wrong. Tucking your shirt in no longer makes you respectable, as I interpret the messages I’m getting. It makes you look like an old man who still dresses like a little boy. It also shows off that gaping faux pas where your superfluous belt should be.

I can’t help it if I become a Social Media Influencer in my Sunday-go-to-meetin’ clothes. (Image: Russell Lee)

My wife grew up in a completely opposite world. She came from the affluent suburbs, where people didn’t have the social freedom to dress like farmers. While I was dodging cow patties, she was dodging the societal pitfalls of matching the wrong top with her shoes. The poor girl had to spend her spare time accessorizing. The closest I ever came to that was finding a pair of matching socks. I’m not saying I did that every day, but I had my debonair moments.

Whenever my shame starts to feel a breeze I reluctantly go out and buy something modern. I don’t make a point to show my new garments to my wife, but she always notices them. I know she’s noticed when she says, “I wish you would just let me shop for you.” This doesn’t always come off sounding like the compliment she means it to be, but I can usually dig down to the loving sentiment beneath it all.

The last time I wore a new outfit, it caught her off guard. She looked at me and let out, “Oh, you look so nice!” before she realized I was wearing new clothes that I’d bought for myself. She had to concede I’d dressed myself like a grown up, but not perfectly so. “Now we just need to get you into a nice pair of Sperrys,” she added.

I think those might be shoes.

29 comments on “Middle-aged man earns right to dress himself – for now

  1. floatinggold says:

    I googled Sperrys. They ARE shoes. But ugh.

  2. Lynn says:

    We wives have to stand together. You can still be comfortable & look nice. Really, it’s true! If you really want to get hip & surprise your lovely wife, do the french tuck. You’re Welcome!

    https://www.gq.com/story/queer-eye-french-tuck-trend

  3. AmyRose🌹 says:

    No idea on Sperrys. I don’t keep up with the labels. I just wear what I like regardless if it is in fashion or not. Hubby is the dress police in this house. It took me about 30 years before he finally conceded I would dress the way I want to dress, not the way he wants me to dress. One of his rules is …. never wear black with brown. I could care less. I do wear black with brown, in fact I did just today. When I do get dressed nicely I get looks at times from those who know me as if they are shocked …. a-huh. I do have nice clothes …. but I prefer casual and comfy. I really enjoyed your post. And yeah, minus the belt and tuck in shirt, I relate.

  4. Susan says:

    Love this! As a 50+ year old woman, I have similar struggles; luckily my husband does as well.

  5. thegsandwich says:

    Too funny. Reminds me of traveling with my husband last year. My son said, “Either untuck the shirt, or put on a damn belt.” He untucked, and was wearing a billowing shirt. He hasn’t worn it since.

  6. CrankyPants says:

    That’s hilarious. My Hubby is a nightmare to take shopping especially when it comes to buying pants. He’s 6 ft 8 and there’s not much out there for that height. He happily lets me buy his clothes but when it comes to pants I have to take him with me. It’s like shopping or a miserable whining kid. I brace myself for the grumpiness and resistance to try things on. Thankfully he’s like you in that he won’t buy new pants until there’s hardly anything left to the ones he owns so I don’t have to be tortured often.

  7. Ironically, just today when I got dressed for work, I left my normally-tucked in shirt untucked for a change. Well, that lasted all of two minutes, because I thought it looked far too casual. And then my boss, who is a few years older, showed up with his shirt untucked. Moral of the story: the struggle is real…

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