What age were you when you decided to stop dressing for fashion-cool, and just dress for comfort?

16 maybe?

I was never a clothes horse and I didn’t have a cash cow or a sugar daddy. Blue jeans and flannel shirts were always fine for me unless I had to dress up for work. Then it was to the nines.

I hate shopping so much, my mum still picks up generic shirts and tshirts and gifts them to me once every two or three years. So my answer is…always.

When enough distance passed that I was able to look at photos of my 80s self with objectivity. I seriously thought I was SMOKING HOT in my crunchy perm, enormous sweater and leggings. I looked like a buffoon. It completely cured me of any desire to follow ridiculous fashion trends.

So when all the 20 years (and 20 year old wannabes) started walking around in their cotton dresses paired with clunky riding boots, in 80 degree weather, I laughed at them as I passed by in my comfortable flip flops.

I have always been fashion-impaired so I don’t think I ever dressed for fashion/style/cool.

This. I revel in the days when I work from home and never get out of yoga pants and a tank top but I also enjoy suits and heels for my days at the downtown office.

I guess I’m an everything in moderation girl. When the hell did that happen?

I never started trying to dress for fashion-cool in the first place.

I dress like Cosmo Kramer-I was “retro-cool” before it was cool.

I gave up on fashion at age 16.

But at what age are you supposed to stop wearing zip-and-button jeans and start wearing elastic-waist denim pants, which obviously are way more comfortable but not fashionable? Because I want to die before I get to that age.

Just a hint of lycra and zip-and-button jeans in the appropriate size can be as comfortable as a pair of sweats. But, as always, if you try to stuff a size 10 into a size 8…you look as if you tried to stuff a size 10 into a size 8.

Yeah, but those aren’t what I’m talking about. You’ve seen those denim pants- elastic waist, no back pockets, usually in a light wash.

My wife has a picture of me from when we first started dating (1987, 26 years ago.)

I was wearing a white button-down shirt and blue jeans.

Yesterday, I wore a white button-down shirt with blue jeans.

I think my “worry about fashion-cool” phase lasted about 19 days, to tell the truth.

And, to be honest, I love being a guy, especially when it comes to clothes. Nothing I have ever really goes out of style. Jeans? Khaki’s? Slacks? Long-sleeve shirts? T-shirts? I expect to be wearing the same sort of clothes until the day I die… in 2462. :wink: