Hmm. I completely share your dilemmas Angie. The only types I like are flat (or almost flat) like the last two pairs, worn over skinny jeans. I do get attracted to them whenever the fashion currents bring them in the first plan, but always pass on because I think it takes a really confident person to pull them off.

I only really like the suede boot. I think that black leather for this look is just too much sass.

Tarty!
I think ankle boots and booties/shooties are the best choice when going for arty and chic. Over-the-knee boots (especially in shiny black leather) scream trash. I think the only time they look halfway nice is on super-skinny women wearing leggings or skinny jeans with a very feminine yet conservative top – maybe a chiffon boatneck blouse.

I agree with you that the suede flats would look effortlessly chic under a flowy dress with tights or skinny jeans! If you have long enough legs, they’d look great and not over-the-top! I think the stiletto-heeled, black leather (patent or not) are slutty no matter what you pair them with.

I’ve never tried them but, on a practical level, is it comfortable to sit for any length of time in over-the-knee boots? Of the boots pictured, the 3rd pair that looks equestrian appeals to me the most.

Ditto on the mocha colored suede boot. They look luscious! I think they would look great with riding pants as well with a great tweed jacket.

I’m not fond of the black leather and especially not fond of the black patent leather. Maybe I’ve seen “Pretty Woman” too many times.

Call me a tart, then! I love the high-heeled version (not the first picture).

I like the the suede boots and the ways you plan to wear them, but I won’t go after the others.

While i think the second pair is kinda sexy I agree with Toni on the Pretty Woman front. Just a little too hooker for the avergage gal. And the flats are a little too swashbuckler for me, more “puss in boots” than “hot in boots”!

I like how the third pair looks but I don’t think I would actually wear over the knee boots. I also have concerns about the comfort of the boot around the knee. Also, I wonder if given over the knee boots and knee high boots if the knee high boots will just usually be more flattering. The over the knee boots do make a big statement while they are fringe, however.

I’m neutral on them. They don’t appeal to me, but I can see how they may make a statement at a club or out on the town. Arty or Tarty will depend on who wears them and how they are worn. I agree with the observations on the comfort issue around the knee.

They can look like hooker boots if one is not careful. I like the suede pair the best but would probably like them even more if they stopped just below the knee. All of them definately scream, Look at me!

I agree- flat, suede ones can look chic, but otherwise they can look pretty trashy. Serena on Gossip Girl wore a pair of slightly over the knee flat grey suede boots with her school uniform, and they looked amazing. Of course, she also has killer legs, so that doesn’t hurt!

If fashion was an Olympic sport, I’d given these boots a level of difficulty of 9.9. Best not attempted by most!

Part of me says they are fashion daring but there’s part of me that wants to put on a pair and get the approval I never wanted from the Ren Faire crowd.

Robin Hood
Robin Hood
Riding thru the glen…

And slightly on the subject, was everyone aware that Friday, Sept. 19th was “Talk like a Pirate” day?

I know this style is tough to pull off, but I’m so drawn to it. I’ve had my eye on a pair of over-the-knee Fluevogs for months … could push me into Tartville, tho!

Aye Matey–we be a bit late fer that one!

I cannot pull off this look, but I won’t say tarty because I’m sure the right girl in the right city would look fab. Even though Nina Garcia put this in The One Hundred, I just can’t do it.

Hot! I think it’s a sassy look, slightly tarty I guess but not in the worst way. I would have worn this look at age 25 or 30. I do feel a bit too old now, or maybe more “sophisticated” or something, so I will pass, but I can definitely see this as appealing on the right woman (someone with attitude and great legs) and with the right outfit (nothing too tarty on top.)

Oh, and yes, I would refrain from the high heel ones. I like the two pairs on the right. Fab!!

I saw a girl around town wearing a black suede pair with totally flat soles, tights and a dropwaist, floaty dress and I thought she looked amazing! It looked so effortless and sweet, I immediately wanted to try, but being so short I feel like perhaps I could only find a pair that goes up to my thighs! I wonder if it’s only a look for tall girls, since it messes around with proportion so thoroughly?

I don’t think over-the-knee boots look trashy per se; anything that potentially looks good on a woman has a chance of coming into the mainstream once our eyes adjust. However, I wonder whether OTK boots throw off one’s proportions when paired with most skirts/trousers we have. So far OTK boots in TV/movies look good paired with hot shorts or micro-minis, not exactly staples in the average woman’s wardrobes!

I like the mushroom color ones and the pink tight ones in pictures, but I’ve started to try to imagine outfits in different configurations. How would these look while sitting? Say in an airport waiting area or a doctor’s office…I just think they would look silly unless you are standing up.

Jane–excellent point. I didn’t even consider the sitting factor.

The only pair that appeals to me is the third pair. From a personality perspective, those boots would work very well for me – I would love to wear them and would be comfortable and confident in them. However, I don’t know how well they would far from a practical standpoint – sitting as Jane points out as well as looking too long on someone who’s 5′3″. If I were taller, I’d definitely go try them out and see if sitting or comfort were an issue – and if not, I”d wear them.

I think it has a lot to do with the specific boot and the specific person wearing them (and, of course, the specific outfit). Like other commenters, I do like the two pairs on the right.

Most definitely Art-y. I always give a lady a nice compliment when I see her in bootware such as this.

They have more tart than art, IMO. The only way they don’t look tarty is if they are flat heeled. A too short skirt will make them even tartier.

I love over the knee boots, and this spring bought a pair of very tall, cream boots, with a round toe and chunky heel. They can be a bit slouchy or can be worn above the knee, and have a gathered detail around the top. All of these elements distance them from the Julia Roberts in “Pretty Woman” hooker look. That said, I still have not figured out exactly what to wear with them.

Oh, wow, I just saw the 50-50s. Those are amazing and killer. I LOVE them!!!

My very modest and stylist 17 yo daughter has the flat suede ones, and she manages to make them look romantic and arty. It is possible!

Generally, I think over-the-knee boots need to be worn by younger ladies, and I also think the lower the heel, the more likely the chance they can be made to work without looking tarty.

Thank you ladies!

The SW’s are my favourite too, Kyle.

I’m not sure whether youth is a prerequisite. I believe that a middle aged woman can pull off this look with style if the variables are right (right boots, right outfit and right body type). Height on the other hand, is a prerequisite. I don’t see OTK boots working on anyone short.

I’ve had a few styles on my feet and they’re not uncomfortable when you sit down if the design over the knee is correct. But I prefer my knee high boots for sure.

Love the mushroom suede ones as well. If only it were cool enough here to wear them!

I agree with Lynn — the lower the heel, the less tarty. Even in black, I think that a low or flat heel does wonders to perception. (Or maybe it’s just that I hate walking in heels at my 5′8″ height — towering for HK.)

The flat ones might be OK with the right outfit…on the right person…who is the right age. The black ones (3rd from the left) are kind of cute…I wonder if you can fold down that flap that is over her knee!

In general, I just think that boots are on the expensive side, so why invest in something that is so outfit specific…spend your money on boots you can wear with just about everything.

I am 5′1″ tall.

I can’t imagine pulling this off without looking like Laura San Giacomo from Pretty Woman.

I don’t have large thighs, but they aren’t super skinny either. This alone should give any woman pause. Shortening already womanly thighs? In a fashion world that lauds long thin legs?

I will stick to my new-old-stock Colt mahogany brown flat riding boots. They are classic, inexpensive find on Ebay, and perfectly proportioned for my leg.

Hate to sound like I don’t love the idea. I just don’t see it panning out for me or my body type. Somehow if I tried to pull these boots off, I would reek of “fashion victim”

But, the pair third from the left are smokin’ hot! (then of course there is that whole height-of-boot issue for us petites! )

I think the last pair are darling and would look fabulous on the right build person with the right outfit. Sadly though, that isn’t me. You have to have the proper length of leg and I think you would have to be rather thin thighed really to pull off that look. I am just too short once again. But with a flat heel on them I think over the knee boots can be quit chic. Add a high heel and they get a bit slutty.

I remember when knee-high boots came out several years ago we called them hooker boots at my high school, but these are the real hooker boots. On the other hand, I think the right pair (like the brown suede pair above) could look great on the right person with the right outfit. I also like the equestrian pair. However, visually I would prefer both pairs as knee-high boots and not over-the-knee. I’m not inclined to try this look, because it only works with really tight skinnies, leggings, or a micro mini skirt, and even then on a girl who is pushing 6 foot and all legs. I’d rather have boots that I can wear with anything. But I’ll enjoy them on the model minority who can get away with them.

I would also call these ‘hooker boots’. Especially if you are like a lot of girls/women I see wearing them with super-short minis. Girls – if I can see cheek, then your skirt is too short.

I just bought a pair of killer heel black leather over-the-knee boots and worn with skinny jeans and a trendy, floaty top they look wicked!

I just bought a black flat suede pair . I dont think they look trashy at all without a heal . I have multiple dresses i wear them with in blue ,pink and purple with black or grey leggings . I usually wear very pretty and fun jewelry to add fun to my outfit . Her in ottawa Canada these boots are a blessiing as i can finally wear dresses in the winter without freezing .:-)

I love wearing otk boots!!!!

I just bought the Duo OTK style boots while on holiday in Bath. I have super skinny calves and have never been able to “fill” a normal size 10/11 boot leg so was thrilled when my 17 yr old fashionista daughter pointed out the store to me. With hubby’s approval, I got the equestrian style (like above) in black smooth leather. Had to wear them on the trip home to the States as I had no more room in my luggage. They did fine. Folded the flap down under my black jeans as I wasn’t packing the right clothes to pair with the new footwear and was seated comfortably for seven hours. Am now looking over my closet – with your advice to wear with neutrals and tights, I see several good outfits emerging. Granted, I am tall (5′10″) and relatively thin so I don’t have some of the issues mentioned above, but I think I can pull this look off and feel rather glamorous in the process. And if I imagine myself as Julia, who’s to know?

I have just received a pair of JC by jessica OTK black, high heel boots and let me tell they are just awesome and very comfortable!
I am in my forties with long legs; pair up with a feminine just above the knee shift dress looks sexy and not trashy. Definitely need confidence and longer somewhat fit legs to wear these though.
These boots are made for walking!!

I just bought a pair of flat black Napa over-the-knee boots by Stuart Weitzman. I am 5′5 and slim, but these boots make me look short. Paired with anything but a short skirt and I look like I am standing in a hole. In the late 80s, I had a pair of flat black suede thigh highs that I wore with a microscopic black skirt and a blazer. Somehow that was better look than the one I have achieved with this 21st century version of the style. Of course, I was 17 the last time I wore any over the knee boot. Maybe youth and height are the keys to success with this look.

I wore black thigh high boots before with a black mini skirt and tight fitting black turtleneck. It looked really nice because the only part of my skin that was showing were my thighs and not even that much. I also didn’t wear any accessories or anything since I didn’t want the outfit to look too attention-grabbing.