my Grandmas both wore dresses all of the time. One grandmother had pants to wear when fishing the other I don’t think even owned pants. My mom grew up wearing jeans and a mans undershirt when she worked in the fields. She wore dresses for work until teachers were allowed to wear pants and never looked back. She mainly wears jeans now with nice knit tops doesn’t even own a dress. I wore jeans until last summer when I broke my shoulder, I can’t fasten a waistband anymore and may never be able to again so I am wearing elastic waisted pants now. So yes I have given up and if you did not know my health issues you would think that I have “given up.”
Of the people you’re dressing for.
If I may be allowed a rant, this thread brings up one of my pet peeves.
I cannot begin to guess how many times I’ve been in a nice restaurant or some such location and seen a couple where the woman is clearly dressed in an outfit she put some thought and effort into; a nice dress, matching shoes, jewelry and handbag chosen perfectly, hair nice. The man, however, is wearing jeans and running shoes and just threw on whatever shirt was available.
Personally, I wouldn’t dream of doing that to my wife. If we’re going to a place where she puts special effort into her ensemble, I should do so as well. It isn’t hard to put on a nice pair of pants, a nice pair of shoes, and to make sure your outfit works.
Anyway, that’s my pet peeve.
I care so little about my clothes, that I’ve told my wife I’ll wear pretty much anything she buys me to wear and is willing to launder (within broad categories of style and comfort).
Drives me nuts when she says, “That shirt doesn’t go with those pants,” so when we are going out together, I’ll tell her to tell me what she wants me to wear. I don’t care, and she does AND she has to look at me.
I long ago went to nothing but white dress shirts, because I didn’t want to have to think about what shirt went with which ties/pants/suit…
Yeah, I’m eagerly awaiting the color-coded jumpsuit future they promised us in 502-602 sci-fi! 
It’s one of mine too, RickJay!
When I was a little girl I went to private school and we had to wear dresses all the time. Then I went to public school, where we could wear jeans and it was like heaven!
Now I’m 48, and given any opportunity I’ll be wearing a dress or skirt. They’re so comfortable, and I look like a nice purty lady (hush! don’t you pop my bubble!)
I’m very leery of becoming “mutton dressed as lamb”, so when in doubt, I err on the side of conservatism. However, I don’t think I’m wearing “old lady clothes” either. Won’t T-shirts and spandex skinny jeans take me from here to the grave?
I agree with your statement. I feel that both people in a situation like that need to dress similarly to each other. Unless if it’s a causal dinner, but still.
I don’t know about that. My wife wears what she wants and I wear what I want. She’s always more dressed up than me. We’re not miles apart, but anyone would say she’s at least a notch above my level of dress.
Certainly if we’re going to an event (wedding, charity gala, etc) we’ll be on the same page. But 95% of the time, she’s looking good and I’m looking like I’m ready to watch some football.
This is easily my all-time favorite user name/sentence fragment combination.
As for dressing my age, outside of work I’ve been wearing jeans/shorts and t-shirts since I was in college thirty-some years ago. I’ll probably be wearing this when they put me in the retirement home - but no Zeppelin or I’m not going.
Heh heh…the dung-coated appendages spring out later. 
Gosh, that is one sharp-dressing dog. 
What’s the difference between a well-dressed man and a dog?
The well-dressed man wears a 3-piece suit. The dog - just pants.
Speaking as a public-people-watcher, thanks! I don’t judge anyone for preferring to be the “sloppy half” of a sartorially mismatched couple, but I do enjoy seeing a couple stepping out with similar dapperness levels. I know it’s merely a kind of informal community performance art, but what’s wrong with informal community performance art?
Other “community performance art events” I enjoy:
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A crowd of summer daytime wedding guests milling around in the sunshine in a riot of cheerful pastels and colors, rather than a funereal-looking assortment of little black dresses.
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Dressed-up people whose outerwear and baggage (purses, attache cases, etc.) looks like a put-together outfit with their hat and shoes, rather than just a shabby bag-lady disguise for a decent-looking outfit underneath (I sin against this principle myself all the time, I’m sorry to say).
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Little children in garments with animal ears/tails/scales/whatever: so cuuuuuute and Where the Wild Things Are-ish.
Yeah, this is kind of me, too (I’m 59 now).
It’s important to me not to make a fool out of myself. And men my age who try to dress like dudes in their 20s or 30s do indeed look like fools.
Work is easy. I’m convinced that the universal uniform of the IT drone is khakis and a blue button-down shirt. So that’s easy.
Funny, I was out to dinner with my sister (approximately the same age) a little while back. She has always been quick to offer me fashion advice (or criticism, depending on your point of view), going back to our high school days.
She pointed out that every single thing I was wearing could have been purchased, and worn, in the mid-70s. I think I was wearing a pair of Levi’s, Clark’s desert boots, a blue button-down shirt, and a tan corduroy sport coat. She was right.
And I am totally cool with that. Because those clothes are just fine, age-appropriate (and, in fact, kind of ageless), and can be worn anywhere, any time, without provoking comments.
Oh, and (edit) I wear the same size now I did in my freshman year of college.
I live in the Colorado mountains. We dress for practicality. Heck, we have a foot of snow forecast for tomorrow and the next day.
I work in IT. I wear blue jeans, usually some sort of fleece pullover and boots/hiking shoes. I could wear shorts if I chose to, but it’s rarely warm enough.
No, no! Resist anonymity. BE “that guy”! Bop through the hallways singing, doodle on the whiteboard before meetings, put out a bowl of circus peanuts, wear Chuck Taylors or Doc Martens. Be joyful, and maybe a smidgen of it will rub off on the rest of the uptight office.
Had a boss who always wore suits to important client meetings, and decided to take me along to one. We had to leave in ten minutes, and I told him I had a coat and tie behind my office door, and offered to shave before we left. “Don’t you dare!” His voice boomed through the halls… “I told them I was bringing one of our most creative problem-solvers along. If you shave and dress up, you’ll look like everyone else.”
Ugh, I hate to pick on you Dinsdale, but you’re exactly the kind of guy that makes my wife and I remark to each other “I’m so glad I’m gay” - the idea that a man can’t be bothered to make an effort for his wife, and that she needs to dress him like he’s a child. So unattractive.
I know a few women whose hubands would need to become total dandies to match the wives; one of those husbands didn’t see his wife without makeup until they had been married for two years. What you think of as “special effort” can be special or it can be their baseline.
Even when I am walking the dog, I am not the better-dressed one.
Of course, Leet the Wonder Dog[sup]TM[/sup] goes for the minimalist look - a collar with his bling (rabies tag, ID, license tag) and always a bandanna in a variety of decorative colors, to set off his fur.
He be styling. Me - not so much.
Regards,
Shodan
As a slight digression - is anyone ever comfortable wearing a style that would have gotten them ridiculed when they were in middle or high school? As a for instance, I’d be unlikely to wear capri length pants, which were scorned as “high water”.
Well, I put on weight due to medications and drinking more and not moving as much as I recovered from a horrible accident.
At Christmas I realized I weighed more than I ever had in my life despite exercising with more regularity in the previous year than I had in in the previous 12.
Then I realized I could use the phone I’m carrying around all the time to track what I’m eating, and now I weigh less than I did before my accident. And I fit into pants I haven’t worn in years.
+1
I let my wife pick out my shirt and/or my sweater when we go out for dinner on Saturday nights. It gives her pleasure, which in turn gives *me *pleasure. Then we both have a nice time.