Only person I have ever seen wear them was Julia Roberts in Pretty Woman. But, you know, I live in the Midwest.

I've been seriously tempted by OTK boots for a while. I'd actually love two pairs - one dressier one and one like the find below for use with jeans or for a more casual feel with skirts. As someone who always runs cold, I'm particularly drawn to these Fryes for their furry lining.

Currently debating these, they had a small sale yesterday. But it was only $75 off

They don't fit my lifestyle but I have opinions based on observations. They look more pirate-y, and just plain costume-y when they than have heels than when they're flat, and the flat heel works better with the more sporty look I like best.

I like the flat ones with short skirts and tights, or jeans and leggings, worn with turtlenecks and crewnecks, simple sweaters with no details. I especially like them on women with short hair, there's a kind of Peter Pan androgyny to the look that is neither tough nor hard looking.

No opinion on age, not an important factor with these, except that it might be easier for an older woman with a more sophisticated wardrobe to style them elegantly.

Admittedly it's all fashion people, but lots of pictures

http://www.whowhatwear.com/pho.....knee-boots

Interestingly, most of the fashion magazines are saying to wear OTK boots with midi hems so that they look like leather or suede leggings/tights. Now, that would be easier with the boots that Anna just posted than with boots that have a higher piece in the front that comes just barely over the kneecap. But even so, I would say that either approach would work. The only awkward length would be one that barely met the top of the boots, so that the hem sometimes covered the boots and sometimes didn't.

Okay I want a pair. But I don't have the lifestyle to wear them.

I am going to move. Then I can wear them.

I have a wonderful pair that I bought 3 years ago...will be sure to put them into rotation this Fall/Winter!!

Anna, thanks for posting those pictures. Seeing the OTK boots in action and seeing how many of us wear them is really inspiring.

I went on the Nordstrom site and saw these this morning -- like the 5050s but half the price AND waterproof, even in suede. On my possibilities list for sure.

I bought a pair last year made by Naya in wide width. I never associated them with a pirate look, though, and am still waiting for the nomen to pull them out with my black leather boyfriend moto shorts and black tights. The boots hit just above my knee cap, and look great with skinny jeans.

OK, so I just bought the Blondos in hopes of wearing with any length dress (including midi), but see here that that may not work,

Here's the thing. I have a pair of knee high (well, not quite knee-high) Tsubos that I've worn in winter with dresses for years but while they're still in decent shape I'm 100% over them (pic below). They look and feel dated to me now. I know ankle boots are probably more on-trend but I need a flat heel and have yet to find a pair of flat ankle boots that works with dresses.

Thoughts?

Had a pair that I wore like Echo posted. Under a dress or skirt that hit the knee, they looked kind of like leather leggings. They were flat, and had almond or pointed toes. I loved them for their warmth on cold winter days. They were a bit rumpled looking due to being a little bigger around the leg than I needed, and after 2 years of hard winter wear were done in.
It was an inexpensive experiment - they were faux, but one of the nicest faux leathers I had ever seen.

I've got your standard black riding boot now. I don't really like boots, but they are a winter necessity.

Thanks, Runcarla, That's my main concern about the OTKs and dresses, the sagging. (Something to check when I try them on.) Also, love your riding boot idea.

I have the Stuart Weitzman Lowland OTK and LOVE them (they come in a wide range of colors). I wear them with skinny jeans and any sort of top or with leggings and a tunic.
I haven't worn them yet with a dress, because I don't usually wear mini-dresses. Maybe I'll try it with tights

http://shop.nordstrom.com/s/st.....c=google-_