High heel shoes, and thong underwear come to mind right out of the gate.
I knw they have thongs for guys to, but wouldn’t wear them on a bet.

I had an early growth spurt and I had to ware what fit. In grade 10 I wore my winter jacket shirtless because no shirt’s fit me. Got very uncomfortable in spring.

I was probably the only kid who wanted clothes for Christmas.

I have some time ago. (quite some time ago) Not anymore! Comfort first. If it looks good also? Great!

Yes, I used to leave off a jacket, because it didn’t good, and just put up with being cold.

I have. A long, very tight skirt. I couldn’t take a full stride in it.

Women’s foundational and supportive undergarments. They used to be worse than they are now, but they were always meant for the (indirect) eye of the beholder rather than the comfort of the wearer.

I remember pulling a damnably tight girdle onto my skinny little adolescent body because that’s what we were supposed to do.

Many times I’ve worn slacks or a skirt that dug into my stomach. I’m more of an apple shape than pear shape. The red lines on my skin from a waistband digging into me last longer than you might think. I didn’t do it to make my stomach look smaller, it doesn’t work like that. The garments simply didn’t fit well.

Shoes rarely bother my feet, I think that’s a common problem for a lot of people, but I’ve still had plenty of instances where I wore painful shoes. Either it was a first time wearing them and I didn’t know they would hurt, or I knew within a short time they would bother my feet, but thought I wouldn’t be out long, and I wound up wearing them longer than I anticipated.

I’ve gained some weight and some of my bras are uncomfortable now, but that’s not usually a problem for me. I used to measure women for bras so I’m good at getting a proper fit, which usually means the bra is not uncomfortable. Still nice to take it off though.

I won’t wear girdle like garments anymore. Funny that when you are thin they don’t bother you much, but then as you get heavier the garments are more uncomfortable. I never wore them much anyway. Plus, you squeeze one part and the fat pops out in another place. I’ve only worn one maybe 10 times unless you count control top pantyhose.

No. I always try my things at the shops. If it looks great but too uncomfortable, I’ll pass. I’m a perfectionist when it comes to those things.

Very occasionally I will but the older I get the more comfort is a priority unless it’s a short event of some kind.
At one point in school I refused to wear blue jeans for several years as I thought they were uncomfortable and ugly. That was pretty weird in farm country…haha!

Not so much anymore. Back in my young adult days it did NOT matter how uncomfortable, IF it made me feel good or look good, I was going to suffer through the pan!!! After I had my stroke, I could NO longer wear heels. I had stopped in a local thrift store & found a gorgeous pair of shoes. I knew I couldn’t wear them, but I couldn’t leave without them either. So, I bought them & put them on display in my den so i could look at them & think about wearing them. They gave me YEARS of pleasure!!!

I look like crap in anything, so I never gave a crap about duds. I just grab whatever comes to hand. Unless my wife catches at it me and corrects me. LOL Must be properly matched at all times.