Caro, Angie's post is so helpful - thank you! It explains why *a* navy blazer is classic, but not alway the SAME navy blazer. It also explains why IronKurtin's avant-garde style looks as fab now as it did in the 90s. Once again, Angie to the rescue!

I think Deb makes a really good point about looks we once wore, but have been in our closet for years and we are bored with. The exact same item might be worn by someone else and look current. For example, a number of years ago I wore a LOT of big, flowy summer skirts. I cannot wear them now. Other people look great in them and they are a style that never really is "out", but I overdosed on them and they still look dated ON ME.

Signature style is interesting, but we don't know that walking past someone on the street. It is helpful to bring it up here to make sure someone really loves an item they are buying, but how many people would really know that something wasn't someone's signature style? If they looked uncomfortable that would be a give-away, but otherwise I am not sure it is relevant to looking dated or not because it isn't information that most people have while looking at you.

And I have to agree that a lot of it has to do with fast fashion. Soon enough, rounded toes will look "dated" just like pointy toes did after the last time they peaked in the '90's. Realistically, unless they are extreme, almost all toe styles are always around, but a lot of people will say that whatever isn't completely current is dated. Same with skirt or dress lengths. Just because something isn't currently being shown on the runway doesn't make it dated, IMO. A lot of things that scream '80's or '90's to me are making a come-back, but they are old enough to be new again. In my eyes they might be dated, but to people younger than I am, they are new. If I wore them they might make me look like a throw-back, but on a teenager they would look new or cute or at least ironic.

There are too many factors for anyone to be able to summarize what looks dated and what doesn't, and what looks dated to me might not look dated to someone else. I think each of us knows it when we see it, but again, we might all look at the same picture and half of us will say it looks good while the other half votes dated.

The subject of datedness always confuses and bothers me. For one thing, I guess I'm not aware enough of details. Round toes vs pointed...huh? I didn't think twice about the collar on kiwichic's jacket and thought it looked great. Others said the collar made it dated. Why??? It's just a normal collar. So I always feel puzzled and in the dark.

The other thing is that the whole issue is subjective. In every single post, some people will say the item in question looks dated and some will say it looks great. There is no consensus, even among people who know more about fashion than the average person. There is no right answer and no way to please everybody.

So I'm going to say my subjective opinion is we worry too much about it. I'm going with ironcurtain...if a person likes it they should wear it. If it looks great...or even if they just think it does...it doesn't have to be the most current thing to be just fine. If something is so on the line as to make us wonder and have to ask whether it is dated, then it must not be all that bad. As Echo says, some people will think anything that isn't exactly the current trend is dated...no room for any middle ground. I call those people teenagers.

".....once again Angie to the rescue."

This is a very tricky question! There are some outfit/person combinations that so obviously scream dated to me (hello Elaine) and yet lots of time I love and admire looks made up of a mishmash of old and new. I do think it depends a lot on the wearer and if her personal style is about being very modern looking, very unique looking, very whatever looking. The main thing is to get a sense the wearer is aware of what she is doing.

In the case of Shannon's jacket, I think she carries it off beautifully and I think it is well designed in that hard to pinpoint way, which raises it above just any shoulder padded double breasted jacket one might thrift. In the case of the white leather jacket I recently posted, I think someone else will wear it beautifully even though it screams 70s. Anyway, Angie's post on the topic is gold of course.

Well... I would personally venture to say that "modern fit" negates dated-ness. I'm thinking of suit jackets as an example... sometimes a really dated lapel/button/stance combo just. looks. dated. no matter how slim and leggy it makes you look. I see this a lot at DFS when sorting donations. But if something made during the same era happens to fall just so so that it looks fresh and modern.

And then some things like Fluevogs - and I would say IK's shoes! - are artsy enough to transcend dated-ness.

And then other things look dated alone but look totally cute and retro when styled.

I guess this is all to say that flattery just ain't enough for this member of the peanut gallery.

Just wanted to say I am loving this discussion. Nothing new to contribute but Una, you are on fire with these thought-provoking threads!

I have a heck of a time judging datedness, unless it is really super-obvious. But then I run into the retro vs. dated question. Some things are so dated that they would just look like a costume if worn today, like 70s double-knit leisure suits with the huge collars, but something like a black leather motorcycle jacket from the 50s or a 40s-style suit would probably not strike me as dated. Generally I focus on figure flattery more than current-ness, and there are some styles that I either love or just don't like so I don't care if they are on-trend or not.

This is a really fascinating discussion. As someone who wears a lot of thrifted items, and gets a lot of inspiration from fellow thrifters, I think so much has to do with styling and how much the wearer owns it, as well as how it flatters.

As someone who was sartorially coming into my own in the early 90s, I have a deep and abiding love of dresses with combat boots (hello, Riot Grrl) - I love the look, and the comfort of it, as well as the underlying meaning ("I needn't adhere to your patriarchial ideas of what's pretty and feminine, Mainstream Culture!"). I don't wear them with a babydoll dress anymore, and I may have changed the boots from my 14 eye Docs to my Veronica Slouch shorties, but the vibe is true, I think. I think it's possible to maintain the throughline, without having to cater fully to the history of the look.

Another example is the ladies of A Beautiful Mess - they have a very vintage-y indie vibe, but they look fresh, thanks to the mixes and proportions. Jane from Sea Of Shoes does this astonishingly well (very fashion-y, but current), by mixing incredibly killer vintage and thrifted pieces with bleeding edge fashion and accessorising.

Flattering *and personal spin* are what keep an obviously out of date item from looking dated. Like IronKurtain (I think?), I really prefer the inspirational piece than the updated, quite often. Incorporating it is where things can get tricky, but a strong personal confidence goes a long way.

Yes, I'm eyeing those snipped square toe booties in my closet suspiciously. Oh....and the cardis might need to be tracked by the NSA, scanning for possible wearer-dating activity. LOL

Actually, I think wearers with a clearly identifiable "personsal style" can break the rules of fashion datedness with impunity. I'm not there yet, although I aspire to be.

I also aspire to spend my fashion funds wisely and avoid buying simply to look like I know what's up in fashion. That creeps too closely to Jr. High thinking for my comfort. When I do replace or need new items, however, I feel that paying attention to what is trending or perceived as dated helps me look like a middle-aged woman still engaged with the world around her -- dynamic, open to change. This does affect my ability to maintain footing professionally and socially, whether I like it or not. Mercifully, I don't live in a trendy environment, so I have years to figure out what's new!

I get especially confused about datedness when people talk about "investment" purchases.

To me that connotes a 5-year item at least. OK, I guess Investment could be in comfort or utility--so I will "invest" in a pair of flats or boots that I'll wear at least once or twice a week for a year or so. However, that is more akin to a general rule of value.

But usually it means, the great jacket, the perfect suits, leather items, bags, and some kinds of footwear, and so on. So how classic can these be and still be current now and ok in 5 years and perhaps not be in the league of the Chanel bag? I mean the EXACT item, not an updated version of it.

Percentage-wise, I see a lot more kudos given on YLF for achieving the latest look than identifying whether an item has 5-year staying power. Still, there is a lot of advice with some caution about how soon something might date, and why, and I appreciate that a lot.

Or are we kidding ourselves and there are very few 5-10 year items and clothing is just darn expensive unless you're a wizard at e-bay and sales/coupons and what have you?

It brings me back to continually rethinking how much clothing I really need (meaning, don't need) so's I'll be more nimble, and being more inventive in ways to make more classic pieces look updated. It really challenges my previous approach to clothing.