See, around my office dockers and a polo is the standard male dress, but those younger than me leave their shirt untucked. Those older tend to tuck in their shirt. I was forever a tucker but within the last year my kids have convinced me that tucking in my shirt makes me look old. So I don’t tuck anymore and that one change sure makes me feel more casual and less business.
I’m a bit of a mixed bag when it comes to fashion and dressing. I grew up poor so it wasn’t like I had much options with what I wore back then. Now I am 50 and I work professionally from a home office and travel to client meetings. My daughters (4 and 9 months) are both in day care at a very good early childhood care facility. I drop them off each morning then return home to my home office. I assume the many of the other parents may draw the wrong impression of me because frankly it is 7 in the morning and I’m headed back to my home office so I’m wearing whatever I took off the night before. That may be sweatpants and hoodie/t-shirt, that may be jeans and a hoodie/t-shirt/polo, but in most cases it is very, very casual. Most of the other parents are in professional attire, from business casual, business suits, or for the nurses/doctors maybe scrubs. Basically, I probably look like an unemployed overweight middle-aged loser when in reality I’m employed. 
Now, if we are going out to dinner with friends or attending an event then I dress in ways that are more appropriate to my age, income level, and the image I want to portray publicly. I’m a bit overweight so I don’t dress in clothing made for 20 year olds but I dress appropriately to my body type yet still fashionable and well-finished.
I think the biggest mistake people make when they are older is continuing to dress as they did when they are younger.
I work in a very conservative industry in an office that is mostly young males with a smattering of mostly (frumpy) middle aged women. I’m a middle age woman but I sure as hack am not, and will always resist being, frumpy. I don’t wear anything fancy, and certainly not expensive, but fashion is kind of a hobby for me. And frankly, I love when people compliment me on my style (at least that’s ONE thing I have going for me :o)
One sour faced beotch, who has thankfully since retired, said to me “who are *you *all dressed up for?”. She was in IT and so wore jeans every day. On the one hand she couldn’t conceive of why I’d bother to dress up for work since “no one sees” me. Yet, she always had elaborate (read "tacky"0 manicures/ pedicures and glitzy sandals.
Sorry, the OP asked specifically about dressing one’s age. Kind of hard to say since to people of the exact same age chronologically can be very different ages in their soul.
I guess it comes down to some people can pull off some looks while others can’t.
Also, for my middle aged sistren, even if your legs have always been your best feature, wearing the shortest skirt possible will not detract from your giant midsection. This is a good example of not dressing one’s age.
My husband is a little bit colorblind - not so much that it affects anything major, but often he cannot tell what shirts and pants go together, so he asks me. I pick out his ties because I can see the colors better.
He misses being in the Navy because he never had to worry about what to wear - it was decided for him.
He’s long said he wishes there were Garanimals for adults - which would suit both those who don’t care to make the effort to choose clothing and those who can’t really tell what works together.
I do care how I dress but I don’t dress according to my age. I have a snow white stubble and a white skunk stripe so I look my age (50), but I wear anything from a tailored suit to ripped jeans depending on the day. I don’t care what others think about that, although it does seem to unnerve some people here in Japan - they honestly don’t know how to peg me sometimes.
I am 66. I wear jeans and a polo shirt with the company logo for work. Off work I wear jeans with Hawaiian shirts in warm weather and jeans with flannel shirts in cold weather.
I think I’m already weird enough under the surface that I don’t need to make a bigger point of it through what I wear.
That, and generally speaking being fashionable requires more effort and thought than I’m willing to put in, between having to gin up ensembles that look right together, clothing that’s not necessarily machine wash/machine dry/no-ironing, and often is very hard to find in my size (I’m about 6’1", have a ‘44’ waist according to most clothing brands, and my chest and shoulders are large too.
64 year “old lady” checking in. For my job at a store owned by Orthodox Jewish people, the clothes have to be “clean and appropriate.” I generally wear T-shirts (that get covered up with the red shirt I wear at work), nice pants, socks and sneakers. Since I have a 34" inseam and a 24" (!) waist), the pants have to have an elastic waist that I can take in.
The biggest problem we have with young female employees is convincing them not to let their breasts “hang out.”
I dress pretty much the same way I’ve dressed for the last 30 years. In many cases, in the same clothes.
I did give up pantyhose. (Ooh what a sacrifice. Sarcasm.) I replaced them with little invisible socklets, if I’m not wearing sandals, and leg makeup (sometimes).
My workplaces have been pretty lax about what you wear. Most recent one: no jeans, and then we moved to not having an office and working from home so–pajamas! Except on days when getting together with the boss at my house or hers.
Macy’s did have a dress code, and you could take it up a couple of notches, but not down. As long as you looked all black from the back. Black pants with gray pinstripe were okay. Colored shirt with black pants/skirt and black cardigan or jacket, also okay. Any color shoes! Not that you can really go crazy with shoes when you’re on your feet the whole shift.
I’m 45 years old and I have no idea how people my age are supposed to dress.
I work at home, so to me, “formal” means shoes. I have one suit. I wore it a year and a half ago to my son’s Bar Mitzvah; I’ll probably wear it again for his wedding. When I want to dress nice - like, when going out to dinner with my wife - I wear my nice jeans, sneakers, and a good short-sleeved button-down shirt, not tucked in. My clothing is casual, clean and good quality. I neither know now care whether it is fashionable.
In general, I like the way I look.
Jumped up Jesus in a sidecar. I have a pair of baggy capris, too long, too shapeless. I wore them the other day with shortie socks in my old lady sneakers. I walked by a big mirror and holy shitballs, I saw ‘my mother’… I have officially turned into My Mother. Kill me now. Next: A cane. I will go to an expensive mall store, flip through racks and racks of on-sale clothes, leave my f’ing CANE hanging up next to the cute pink linen resort-wear section…
I value myself.
Therefore I will wear what I damn well please. You don’t like my cargo pants, you can look at somebody else.
One of the things I like about farming is that what I please to wear is for the most part suitable for the job; though occasionally I please to wear a shirt that’s too fragile to stand up well in the field.
I’m 68, which I think puts me in a range in which I can claim old-lady status if I feel like it. One of the advantages of old-lady status, IMO, is that you get to quit worrying, if you ever did, about what people think you look like (exception, as always, for your partner if you’ve got one; while you shouldn’t be worried about the subject if the relationship’s any good, if they like to dress up and want you to match I think it’s good to be nice to your partner and that’s enough reason to at least sometimes wear what they like). But most people in this society are going to think you look like an old woman and quite a lot of them are going to quit looking. Wear what suits you. Which, of course, is going to vary depending on who you are. (And, if you can manage it, cultivate for suitable occasions a voice which says ‘You WILL include my voice in this conversation.’)
– “clothes that fit and are well-made” would have to, for many people and especially for many women, be custom-made; thereby requiring financial resources many people either don’t have at all, or would only have if they chose not to do other things more important to them. Off-the-rack clothes are made in a limited number of shapes; human bodies come in a much wider range.
If you don’t already KNOW what to wear in various circumstances, the advice would be to dress conservatively so as to not stand out from everybody else, whether by over- or under-dressing, or choosing the wrong style. The rule of thumb is, if everybody keeps staring at you, you’re doing it wrong (or very, very, right).
Your age really has nothing directly to do with it, unless your favourite dresses or suits are 50 years out of fashion.
I was told I had to wear a suit for work – was I doing it wrong? 
The last time I wore a necktie was to go to underground cartoonist (and author of Maus) Art Spiegelman’s gallery show last winter. I also had on a topcoat, vest, pearl-grey bowler, and sneakers. I was pleased to see that Art was wearing nearly the same, except with a black fedora instead of a bowler.
Bohemian New Yorkers have always dressed like freaks. My wife rarely wear tee shirts with things written on them, because she feels that folks over 40 shouldn’t do it. But all the other old men in our Brooklyn neighborhood do. Over the past three days I have worn tee shirts advertising the Maine soft drink Moxie, the City Lights bookstore in San Francisco, and FDR’s National Recovery Act.
Heh. I’m a woman, but I used to wear my hair center-parted and long. My mom always said my part looked like it was struck by lightning, because I never bother to make it perfectly straight.
I’m still gonna dress like a stoned teenager. T-shirts and cargo shorts most of the time, sometimes overalls, and jeans in winter. If there’s a good reason to wear a button down shirt in the era of cotton knit, I still haven’t heard it.
First thing I thought about when seeing this thread title was older folks desperately trying to look young by dressing in “what the kids are wearing.” At one time, that would have meant mini-skirts and go-go boots, tho I don’t follow fashion trends, so I have no idea what the kids are wearing these days.
Honestly, I don’t much care what people wear, but I do find it tacky when undergarments or too much skin are on display. It doesn’t offend me or scandalize me - it just looks awful, IMHO. I also crack up when I see men in jeans with smaller waist sizes buckling them under massive guts. If that’s your fantasy, dude…
Dressing appropriately for the setting is of moderate importance. It is easy to attach to much significance to fashion.
Even some bankers and lawyers are moving away from formal clothing. This is a shame. It is important to be comfortable, formal clothing does not have to be constrictive if you choose the proper material for the climate. Some work settings are much more informal.
It is common for groups to want to differentiate themselves. Slang and fashion are easy ways to do this. I am not likely to wear low hanging jeans, exposed underwear, exposed belly buttons, gaudy jewellery, clothing with attached price tags or prominent brand names (with occasional exceptions). But T-shirts were objectionable when they came out, and some old folks still frown on shorts.
Clothing should fit and flatter the figure. So probably not everyone should expose their least flattering parts, regardless of age. But if you want to, it’s a free country.
I think the trends towards more colourful clothing, comfort, less required formality, fewer “rules” and mixing, say, jeans and sport coats are good. Still, many folks don’t dress very well. They don’t have to. Nothing wrong with prioritizing other things. But it is easy and fun to develop an individual style, and a generally positive thing as well.
I don’t think most older people would want to wear clothing in public that makes them look like a goth, cosplay victim, is very revealing or makes strangers quake with laughter. But if they want to, all the power to them. My own tastes are slightly more formal.
When I was little (born in 58) older women wore short sleeved house dresses and short permed hair. I thought, that’s not me, I’m never going to do that.
As I got older, I saw Cher didn’t do that either so figured it was more lax now.
I am 60, and I do wear yoga pants and sleeveless tank tops in the summer.
I don’t feel that’s dressing too young for my age as I have the figure for it, but theres a point where one would go over the line, such as hmmm, I actually don’t know what that would be, maybe a mini skirt?