I've seen them a variety of ways and I think the best thing I can say is that they are Less Unflattering on most people with darker hose. I don't think they are a shoe that does any esthetic favors for most women's legs or feet with a dress if they are over about 25. But they look okay if everything from leg to toe matches or blends.

This post was edited by palimpsest on Thu, Nov 6, 14 at 9:02

Thanks, pal...that puts me out by a few decades!

Certainly don't want to be rockin' that Phyllis Diller look!

This post was edited by AnnieDeighnaugh on Thu, Nov 6, 14 at 9:18

I think they can be young and hip, in good ways, as long as the person wearing them isn't an apple. Not a good look for apples.

Casually, I like them with jeans rolled up, boyfriend look.
That seems more current than jeans tucked in.

My 6th grader just wore black suede ones to a dance with a short dress. Bare legs. It's done. Was a new one on me.

Of course it's a little easier to rock the look at the sixth grade dance. : )

Personally I think "Less Unflattering" is about the only variation on your question, as Pal implies. Never ever chop up your legs.

The reason I ask is, I'm a fan of the Vivienne files and one of her looks includes ankle boots with a dress, and I'm like, huh? And she doesn't get into things like hose...

I have always liked ankle boots with pants. With skirts/dresses, I think one needs to be young. Older people attempting that look resemble aging elves, IMO.

Sas, elves no less...what an image!
Lol!

I think the very young would probably look a little boring if everything they wore was flattering, but I think as you get older it becomes more important.

I don't think there is anything the matter with trying to be trendy in some way but It think most people have to be very careful about how you do it, the older you get. "Characters" can get a way with a lot, and I also knew an elderly woman that wore miniskirts, but always with tights, always very expensive, and of course she was very small and probably weighed 100 lbs.

Another of my mothers friends wore dresses that were so low cut that she appeared naked at the dinner table when she sat down, but she had a Marilyn Monroe figure at 75 and was extremely young looking. I know this embarrassed her children, even though she actually looked good.

I wear ankle boots but only with pants and never with the pant legs tucked in. Even with higher boots, I don't tuck my pant legs in because it just makes me look shorter and stockier.

I recently bought a pair of Born ankle boots that I am loving. They're totally flat heeled, so really not that flattering because I really "should" wear more of a heel, but they are incredibly comfortable and work well with a couple pairs of jeans I have in shorter lengths (so higher heels would make the pants "high waters").

I think the only way ankle boots look flattering with a dress is if the dress is above the knee and the legs are slim and long. Ankle boots with rolled pants for me!

Sueb - what Born boots do you have? I love Born shoes and I like them flat. Maybe I need a new pair of ankle boots....

I think they work OK with very long skirts.

....aging elves...I love it, lol

I don't totally hate Phyllis diller getup--wished I were so bold as to do something like that. She looked like a happy aging elf.

Gibby -- these, from J. Jill. Some of the reviewers say they run small but I found them true to size (with lightweight socks).

Here is a link that might be useful: Boots

Sas, I don't think I'd ever be mistaken for an elf, old or not, as I'm nearly 5'9, lol. I agree with Pal...I don't think age should stop one from wearing what's current, trendy, or, most important, flattering.

No way should you try to tuck pants into booties. Mid-calf boots are another matter. Depends on what you're wearing those with too, like skinny jeans.

Sue, your link took me to a Pottery Barn page.

Just to clarify, there is a difference in booties and ankle boots.
Ankle boots can have a seven inch shaft or so and still be sold as an ankle boot. Booties tend to have a 4"-6" shaft at most but are typically scooped with nothing on the ankle. Booties are the lowest boot.

Oops! The boots are at J. Jill, not PB ;)

Here is a link that might be useful: Boots

I'm such a sucker, I just bought these booties:

Here is a link that might be useful: Kork Ease Booties

And this is how I'll wear them. However, since I'm not in the Jennifer Aniston realm, I'll be wearing an actual shirt or cardigan:

Thanks Sueb! I have tall Born boots with that same super flat sole. Hmmm...I might need to consider those short ones.

A classic look: a cozy plaid woolen skirt (mid-calf length), a warm jacket or thick sweater, dark opaque tights (black, brown or grey) and ankle booties (low or medium heel).

One of my favorite combinations for those invigorating autumn days.

Here is a link that might be useful: How to wear ankle boos with skirts

Magdalena: I prefer booties with a wedge heel. Sometimes the regular heel looks a bit "dominatrix"to me. As for the Jennifer Annisten look--don't forget the bra!

I have flat as in totally flat, black suede booties which I got last year. I have worn them with all length dresses. skirts, with black opaque hose and also with jeans (tucked into the booties).
I think it looked very nice and I am 60, average height (used to be 5'5 now about 5'4 :) and could lose some pounds. I don't usually take to the young trends, but this was very comfy and looked updated.
I did not feel foolish at all wearing them and even got complements.
I think the ones with heels like the pic above this post are really cool but I look at them and my feet hurt. The wedge ones might work but I don't know.

Those boots are cute, not that I and my bootie could wear them. But esp the ones on the vivienne files...they look like what we used to call jodphur boots and I just can't imagine them with a skirt or dress. I think I'm simply not young or wild enough to do it. Here at least they are done with socks....and on a model with legs a mile long.

I think that will be my new mantra...too much bootie to wear booties!

Yeah hence the problem with models. It's pretty hard to make that model look bad, although the stylist tried mightily hard here.

I know if I wore that i get up it would elicit outright guffaws, and rightly so. I think most women in America over 19 and 105# cannot pull that off.

Still thinking elves...

:)

There are ankle boots and then there are ANKLE boots. The ones pictured in the Vivienne file I would NEVER wear with anything but jeans. Call me style challenged but that juxtaposition look is lost on me.

The vivienne file boot is known as a motorcycle boot or more commonly, Moto boot.
I have several but wear them with jeans.

Magda, that look is very popular around here, especially with the college crowd. I have seen several of the wedge boots.

I am not big on boots, mainly because I hate my feet covered. LOL So the least shoe I can get away with. I only wear boots if it's really, really cold.

I agree with looking stylish at any age, but IMHO, wearing something too young looking for a certain age is not stylish. It can become almost comical (as in the elf comment - love it!). Working part-time on a college campus, I have to remind myself, I'm a bit too old to be wearing the same outfits the 18 year olds are.

I saw somewhere recently that if you don't have skinny legs to make sure the ankle boot dips down in front-like the pic above with the skirt. I've seen them "dip down" more than that though.

Not a fan of bootees of any kind with skirts, and I finally now have a name for what I've been seeing....the Elf look! I have seen people wear short boots with certain outfits that did not look terrible (to me) but they've been few and far between. When they're covered by slacks the height of the boot is a non sequitur.

Annie, in summers we all (kids and I) wore jodphur boots that zipped on the side for riding because it was too hot for regular boots. Who knew that was going to morph into a fashion, lol??

I had to post this. I don't think we can speak in generalities about anything, including what works for every body type. Hillary Clinton would definitely be an elf. And I've seen a few 'elves' of various ages at work who should leave off the booties/ankle boots.

BTW, booties, ankle boots, and a new term 'shooties' (half-shoe/half boot?) - they are all the same category when you look at a shoe website.

Salonv and Annie:

The outfit in the picture I posted would work with lower heel boots like in the picture below. The top boot is by Gabor, and the bottom one is by Clarks.

I love booties and wear outfits similar to this one to work often.... blazer, ankle pants and cute boots. I have a pair of Clarks that I'm really fond of.... they're comfortable and aren't slippery at all on wet floors, etc. (we get alot of snow & rain this time of year....). I think these looks are all about showing of a GREAT pair of boots. :)

Another kind of skirts to wear with ankle boots: British tweed. Again, classic and timeless.

Here is a link that might be useful: Brora - Scottish Cashmere

Those tweed skirts would look better with wellies!

(I categorically reject the term "shoetie." Just because.)

Didn't read all the responses, but agree with Pal.

If not the same color, the look chops me up like capris do, IMO.

I think whether or not booties look really great has less to do with age and more to do with body type and attitude. Jennifer Aniston is not college-age and she looks fabulous in those boots, as would anyone at any age with her body type (trim and fit), and a youthful vibe. I like the look of them better with tights or socks, rather than with bare legs.

(I categorically reject the term "shoetie." Just because.)

I feel the same about the term "jeggings". ugh

I still think those long skirts just look off with the boots. The reason those models *sort of* pull of the look is because they are long and lean.

"The reason those models *sort of* pull of the look is because they are long and lean."

True that.

In my opinion, ankle boots go better with fuller calves. Most skinny models I saw online don't look good in such boots because their legs end up looking like pencils in a glass. Also, ankle boots tend to over-emphasize bony ankles. The fit around the ankle is crucial. It shouldn't be too loose, otherwise there would be that "pencil in a glass" effect.

I believe thick socks and dark tights help balance the heavier visual weight of ankle boots. Pants and thick fabric skirts do the same.

In the picture in this thread Jennifer Aniston's legs don't look skinny in those jeans, and her boots fit snugly around her ankles (the socks help that!). She has just enough feminine volume in her jeans-clad hips and legs to pull off the chunky boots.

I went shopping yesterday and there are probably more boots than shoes on display.

I had a real flashback as I was walking by Frye boots and Beatle boots!

But the styles of clothing. Yuck. I used to look in store windows and lust after many outfits, but not yesterday. And the fabrics are getting worse all the time, let alone the construction. I can't get past wearing something that feels like a plastic bag blended with sand paper. Stick your hand into the rack and the fabrics literally feel cold. How are you supposed to stay warm in winter in that stuff? Clothing knows nothing about fit and ease any more...everything seems stretch to fit. Very disappointing. Especially when they can do so much more with synthetics these days. I still have a blend shirt from when I was 14, and it feels and wears like cotton, but never ever wrinkles. If they did it then why not now!?!

Maybe I'm just getting old.
:(

As a life time fan of Frye boots, I recently added these to my collection. They were a third off and I could not resist the sale. So far, I have worn them with rolled up boyfriend jeans.

Kate Middleton (love her style) wears ankle boots all the time with skirts and hose. I think ankle boots and skirts work best when the boot is a similar color to what's worn on the legs. Black boots with black hose for example.

I agree that Kate's look works. It's because the it's all the same color making an unbroken line to the legs all the way down to the toes. Nude hose or a different color boot would ruin the look.

Agree about the matching color of the hose and boots. Also, Kate's boots fit snugly around her ankles, and the visual weight of her dress balances the boots well.

I saw two bare-legged or natural colored stockings variations of this this morning.

Both women were between 25 and 30, both had black boots and both were dressed in black with pretty short skirts.(several inches above the knee)

1) had a full short black skirt and an extremely voluminous 3/4 belted jacket with a very large collar and a lot of fabric. The fabric was a Japanese looking print and the cut was Japanese-inspired looking

The boots were very short barely more than a shoe that was filled-in, sort of.

2) had on a short tight skirt (black) and a black tailored jacket and she had on genuine Boots that came up over the ankle a couple of inches.

I think it looked fine on both of these women. But the first outfit in general would have been very unflattering on a lot of people. She had the trifecta of tall, thin and young. The second outfit was more universal, but I think it depended upon the monochromatic outfit where everything was the same color (or at least not distinctly light or lightweight on top) and I think it relied on the fair expanse of leg between the top of the boot and the hem.