I suppose one can also ask why 40 and older women dress like teenage girls and think it's cute.

Where would I go to find the definitive, authoritative information concerning what age and how anyone should dress?

As a woman who is in jeans and tshirts whenever possible I can’t fault the guys and imWAYover 21.Americans in general dress for comfort.

Every time I read a new excerpt from "Tales of the Literate Hiker" it becomes even clearer to me that @LiterateHiker is really Elaine Benes.

I'm not gettin' my fingerprints on this trainwreck of a topic!!!

Y'all crack me up.

The way men dress has degenerated at a steady pace over the years, and younger woman do not even realize it because this is normal .Some men do not dress appropriately for the occasion.I was recently at a funeral and there were men there that did not have the decency to even wear a dress shirt and trousers.The unshaven dirty grungy 5 day old beard look is an example of what people once found unsightly but is now accepted. Whenever i look at photos of men walking around Manhattan or any major city 60 or more years ago it’s shocking to see how much more civilized and well groomed they appear to be ,but that’s only my opinion.I purchase most of my clothing in thrift shops and the salvation army,even though I can afford better. You do not need new designer clothes to look presentable.

As an ex-clothes horse I am disappointed that you rarely see a man in a bespoke suit and many tailors and haberdashery shops have gone the way of the dodo. Even a new, clean pair of jeans, boots with fresh polish and a polo shirt seem to be considered overdressed these days and I think it is a shame.
On the flip side, seeing women in their prime or past it for that matter dressing like teeny boppers is also disappointing and unsettling. Dressing like a kid does not make a woman look younger, it just makes her look silly.

It is refreshing to know that some woman still believe proper attire is an important attribute.This not caring attitude is one of the reasons there are so many Disheveled slobs walking around .
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When a man does not dress appropriately for the occasion it gives the impression he does not give a shit,but hey some people want to give that impression

If you're talking about a first date... neat and clean jeans or shorts are fine by me. I'm a casual person. I like comfort in my clothes. So I would want the person I meet to be comfortable too. If they wear khaki's that's fine too. Clean is the main issue for me otherwise, be yourself!

As someone who tends to be drawn to long haired (yes, even man buns), and/or bearded types , I giggled a little at your description of Alaskan guys.

However, I don't see "well groomed" and the "rugged look" as being mutually exclusive. Hairy headed guys, that are reasonably clean, with shiny well kept hair, and a shaped beard are definite turn-ons for me. Of course, being here in the South, while flannel shirts are not worn too often, shorts, t-shirts, and work boots are. Along with jeans and T's , even cowboy hats - as we do have plenty of real cowboys here !

Then too, riding motorcycles often presents just the look I like. I prefer good fitting jeans to khakis any day.

And of course it depends if someone is coming straight from physical work - I make allowance for that. But then, seeing someone all cleaned up and polished - even if their hair is long, and their beard is full - all fine by me !
Men like Jason Momoa, Sam Elliot in the movie "Roadhouse", Jeff Bridges in hairy mode, or Bradley Cooper in "A Star is Born" (be still my heart !!) come to mind ...

All this said, with that certain personality that appeals, any hair, or no hair at all can work too !

I'm a lumberjack and I'm OK....

I lived in Anchorage, Alaska for 5 years and can tell you that I enjoyed looking the way you described and still had zero problems with Women. Alaska is a mixing pot and we’re not all just fishermen and oil workers lol.. I was working in upper management there and wore a suit daily. My beard was pretty kick ass

You said "on the street." That's not a date. They may have been going to or coming from work, work being manual labor. Did they dress like that for dates too?

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For a woman who claims to want to date men, you sure shit all over them. Often.

Also, you are comparing men on the street, who live in Alaska to what you want to see on a first date. ....
Apples and oranges. ....

Give it a rest. ... I'm a woman and sick of your crap. ... I can only imagine how the men feel.

A date , is going to be as good as it gets . While we do work and cloths get dirty and worn while working , a date is , in a way , similar to a job interview . If you make absolutely no effort to be clean and put together , you're not going to get the , "job ." Men prefer to win the , " hotty ." Do men go looking for a woman who's wearing the boots she wore , when she went to slop the pigs ? The blouse she was wearing , when the baby threw up on her shoulder ? The dress she wore while washing the dishes , that has the sudsy line across the front ? Crud on her hands , because she had to change the tire ? Everything is down hill after the dating . If you don't have enough interest or respect in a date , or even a meet up , to clean yourself up , and put on something a bit nicer than you used for work , than what makes you think a decent woman would be interested in getting buffed up for you ?

People dress the way they feel comfortable. Respect that instead of making these remarks. As long they behave properly, why make such a fuss about what they wear?

How about this for a first date outfit?

She wants FIT and WELL DRESSED OKAY EVERYONE?

I myself don't mind the muffin top that can come with age.... Life happens.

I've met some nice men with little muffin tops going on.... and my waist isn't spectacular.... (Hey I'm disabled).

What's inside is way more important than what's outside. Though if someone can't clean up a bit for a date - I would suspect depression. (And probably get them in touch with some help). Yup I've actually done that.

At least if people dressed how they want, others would have the first clue of what they might not want...the controllable exterior, ie. clothing, grooming, might be the hint that a person might not be suited for you and vice-versa.

I have met many men in a nice suit that just did not match up to who they really were. I have also met many men in jeans and a t-shirt that were pretty down to earth.

On a date, I think you would find the men in Alaska would be clean and neat and still be themselves. I doubt you would still like them because inside, they truly are more rugged and individualistic, independent and outdoorsy or else they would probably be working in Manhatten...clothes do make the man so I would look at it as a gift if that type of man is not your type.

Personally, I would probably pick torn jeans over khakis...

I always clean up for date. Sometimes even if I am going out by myself for a few drinks.
I always seem to get compliments from the younger ladies.

What's a khaki?

I’m staying out of this conversation because sometimes people are too judgmental. “Live and let live.”

I find I get better service and respect when I go out or attend a meeting and dress with a sport coat and ironed shirt. That said I like working around the homestead in the garden, splitting wood, mowing the lawn. At that time I dress comfortably which my wife claims homeless wouldn't wear.

This is Alaska... not Los Angeles?

I get ripped on all the time by my Lady for me casual dress, but to be honest it's all about comfort. Nice looking clothes just don't feel quite as nice on the body....