I'm with Suz on it has to be weather appropriate. With Angie on the heel has to be MY comfort (nothing over 2.5 for me and I'm trying to amass a collection of 1.5 inch pointy toe flats) and I'm going to wear slim not skinnies and BFs with this look. That's my personal interpretation and I can't wait for winter to be over to break it out!
To me it veers into trashy when the clothing is Too bodycon (either tight or revealing or both) AND the heels are OTT. Otherwise classic, not too young if adjusted for yourself and not too sexy same reason.
Oh and yes you can pull this look off, just make it yours.

It's a classic not too young, not too sexy, it's a great way to elongate the legs.
love the outfit on photo 3 with a lace top, black pumps (not too high). Chic and classy!

it took me a while to get comfortable with this look, as i also remember this for the the 80'. in the new england town i grow up in, it was jeans with heels vs preppy, and this look was considered very "fast" and urban. at the time i would wear this look one day, and dress as a total preppie the next.

i think because i wore it in high school, i also wondered if this look was to young for me. but the more i see it, the less i feel that way. i should add that for me, a high heel is 3 inches, and usually i wear more of a kitten heel.

I could not do heels that high, I would topple over for sure! And I kind of agree with Suz, it seems strange to wear open shoes in winter. My foot would freeze. I do like the look though, and agree with Angie that it can be done with a lower heel. I also like flat boots. It's probably not quite as sexy though.

I agree with JJ. When you pair skinny jeans with sky high heels or platforms, the look may turn trashy. But BF jeans, straight legs or a slim bootcut with a heel is NOT too young or too sexy. And I'm not just saying that because that's what I'm wearing today for casual Friday. LOL! I've paired slim bootcuts with a striped tee, black blazer and 3" heel booties.

This can be a fine line between tarty and "cool". One thing that I noticed is that most of the pics are RATE or have a RATE aspect. Most of the pumps are not "traditional, classic" pumps. I thing that proportion is important here too. That is that if you wore a tight, skimpy top or mid-riff....well, hello tarty girl. I think that you have to aim for "fun".

Yikes, I like this look. I hope it doesn't look trashy or too young. I am a 56 year old pear and when I wear heels (around 2.5"), I feel like it makes slim pants look more proportionally correct. And also, I feel more elegant, because of the heel. With flats, I just seem to feel too low to the ground. Haha I love the elegance of the pointy toe.

I look so much better in a pair of jeans when I wear a heel, even just a couple inches totally changes the look for me. I think all of these looks are lovely and something I will emulate come spring/summer. I like how this look kind of dresses up the jean and dresses down the heel, great combo.

I like the look and am planning on some combination of pumps and jeans when I go out to dinner tonight. I haven't quite figured out my outfit but heels and pants are on the agenda. I agree that's it's all in the styling and has the possibility to look trashy (which I hope to avoid with my own outfit).

I am on the same page as Tina.b and morethanbeige. I like the look a lot and see nothing trashy or skewing juvenile about this look, especially with the examples you've posted.

I really like the look and think that it can either look classic or trashy depending on other elements in the outfit. If wearing 2.5/3 inch heels with skinnies but the top is flowy or voluminous, I think the outfit is both stylish and can be any age appropriate. Take those same skinnies and heels, but add a low cut or clingy top, you've now ventured into the trashy zone.

I can't imagine you ever looking trashy or mutton dressed as lamb Denise and am sure you would pull off this look beautifully.

I also really REALLY like the pumps with the BF or distressed slouchy jeans - the juxtaposition of dressy heels with jeans just tickles my fancy. I'm dying to try this look with a pair of black patent pointy toed kitten heels once the weather allows.

The short answer: no.

I think to some degree it depends on getting the details right, but honestly, jeans with fancy high-heeled shoes is a look I feel very comfortable and confident in. (I'm 40, for the record). I read somewhere once that a woman can rock dramatic shoes at just about any age, even when she's too old to wear certain tops, bottoms or dresses. I agree with this. And jeans are a really good way of dressing down the fancy shoes so that you don't feel all "done up".

I personally wear them with skinnies and a crisp button-front shirt, as I feel that the shirt always looks a bit more mature and dignified than a tee shirt. And once you're past a certain age, looking dignified is a good idea. Another alternative is a flowy batwing top, as long as there is sufficient coverage -- anything too bare might look wrong -- or a nice fitted tee shirt underneath a suit jacket, especially one that is not cropped.

As for high heels with boyfriend jeans, I've never tried that look, but I bet you could make it look fantastic.

I like the look. Pretty much anything I might have said about it has been covered but I would say you could easily give it a whirl if it tickles you fancy without risking the "too young" statement. My grandmother wore 3" heels with everything and I loved her style.

I like the look and I don't think it looks too sexy or inappropriate. (I mean, I guess you could make it overly sexy by wearing skintight jeans and really high pumps, but the way most people and bloggers do it is fine). I personally don't wear it just because I don't wear pumps at all - they are hell on my feet.

It looks fine to me, but I probably won't be wearing the combination. When I'm in jeans, I'm usually after comfort. Heels take the comfort level down several notches for me.

So interesting!

Denise, you do crack me up.

Oh my word. I have been advocating wearing heels with jeans for years!! I don't see it as trashy at all. Not skewing young either, nor anything but a great look. The bloggers look fab!

Personally, I'm not a fan of platformed pumps. I am ultra close to developing a poison eye for them and severely high heels in general. But I like to have a very short list of "posion eye" items. You CANNOT be a successful fashion stylist with a long list of items and looks that give you poison eye.

You look great in that look and certainly not too old for it.

I like the look with ankle-short skinnies as I would with short cigarette pants. I had a terrific pair of skin tight Roots yoga jeans (which I sold in a moment of recklessness), which went so well with pointy high heels. Sigh.

Suz, totally with you on the discrepancy between what bloggers of north climes are sporting and actual north climes. It makes me wonder if the "What I wore" really was worn. I think the whole point of exploring fashion in a more human way (as opposed to what big companies do) is to try to actually wear it.

In seasons other than Summer, I like to wear my shoes with knee high nudes, like Angie in today's post. In the winter when the weather is very cold like now, I wear a pair or wool socks over it inside my boots, which I remove at the office when I change into my pumps or other shoes.

I travel from office to office for my job as a corporate French teacher. The other day I had dressed with Angie's black-white-blue formula, and had brought my heeled Oxfords to complete the look once inside. Except it is extremely cold here right now, i'm talking polar, -20C, so much so that my black pants were not enough so I thought I was being clever by wearing nylons under them. I completed the protection with thick wool socks to be removed inside, when I'd slip on the Oxfords. Nylons - especially the thick, circulation promoting kind I use for this - offer an okay extra protection under pants which are already thick enough. However when I arrived I quickly realized the heating system was cranked up in that particular office, and that I'd never be able to sustain 3 long hours with my nylons under my pants. So I removed my nylons in the restrooms and put them in my purse. Except now I was left with no socks. Which wasn't so much of a visual problem - the pants were long enough to cover the top of my high-vamp shoes - as a comfort issue. It was horrible! I sweated in my shoes for the rest of the time, as was so uncomfortable that by the end I took a toilet break to sneak my nylons back on!

I don't think this look is necessarily too young or too sexy; it all depends on the styling of course. You could totally rock it Denise!

I think it can be done right, like EA does, who's not really young.

Again, my mental block with wearing this look myself has to do with growing up in a time where jeans and heels were considered a bit tacky Interesting that only a few people here have similar memories. Perhaps it's an age and geography type of thing.

I like it. It's classic if you ask me. But, as always, there's a dark side and a light side. Dark side: trampy. I think, unfortunately, of Jessica Simpson. Or Olivia Newton John in Grease at the end there.

I think, perhaps, as a person really gets up there - it might be best to forego denim. Might happen naturally tho. Stiff denim interferes with the digestion.

I like it!

I am 47 and I've been doing this look for years -- when weather permits, and for going out (not a daytime look). The majority of my heels are all around 1-1/2- 2 inches max though.

For example:

1) With shorter pants lengths (ankle, or the dreaded cropped), adding a pointy toe heel seems to look better with my petite proportions, i.e., not so stumpifying.

2) I still like wearing my skinnies with scrunch, even if this trend has moved on, because it adds weight and balance, I guess. I like then adding a round toe heeled pump, to add even more weight.

3) I have often worn my black ponte knit skinnies, which shrunk in the wash and are now an awkward ankle length, with strappy wedges. To my eye, it looks totally cute, even a little retro. But maybe my eye is messed up!

4) With skinny jeans adding a pointy toe heel just seems to elongate my leg that extra couple of inches I need to have the "ideal" proportions. My legs are average-length -- not really all that stubby (that's in my head, my tape measure says different). I can handle ballet flats but I much prefer adding a heel, activities permitting.

I did not know this was trashy -- never would have occurred to me.

Coming back to say that no, I don't think it is either young or old, I see it as ageless. I have no doubt that you can rock this look Denise. You would make it tasteful.

I don't really remember a time (since I started paying attention) where people weren't wearing jeans with some form of heels, depending - irrespective of what they're being worn with - on what kinds of heels were in fashion at the time. Ballet flats come and go, oxfords and sneakers as well, so aside from heels, what else is normally worn with jeans? Loafers maybe?

I don't think the look is inherently either too young or too sexy, but like anything else, could be made so by the actual items being worn - a 3 or 4" pump is different than a 6" platform lace up sandal, and a skinny or a bf jean is different than a painted on pair of jeans. Though, to be fair, I wear jeans and heels all the time so I'm pretty biased!

ETA: You should absolutely try pairing your jeans with your heels!! You look so great in all of your jeans already, heels will be unbelievable!

I think it's because jeans started out as being worn by factory workers and cowboys, and then later on teenage rebels (James Dean), and then hippie wear. They were worn with boots, sneakers, and other flat shoes, probably platforms in the hippie era. It wasn't until the late 70s that we started seeing designer jeans (Gloria Vanderbilt, Calvin Klein) and people started wearing them with heels. I distinctly recall a "trashy" or "tacky" association with the 80s-style skinny, tapered jeans and pumps (specifically pumps!) -- just as there was a "rebel" association with denim in the 50s. Nowadays, I think that "tacky" association has gone away, as we see jeans worn with heels a lot.

*love*

i'm a platform shoe gal. must have a chunky heel and a polished finish preferably in black, bonus points for suede.

wear with knee high stockings in the winter.

ea is my fashion icon.