Thirded.
There are exceptions, but not with what I can tell regarding your specifics.
I could see ankle boots with a knee length skirt IF it was a skirt you could wear opaque black tights with and the boots were also black and sleek looking. Not only are your boots light brown/tan, but they’re (from the explanation you gave) clunky looking.
OK, I have to admit, my otherwise sleek new boots have exactly that problem. They get all pooched out right above ankle level.
I can partly correct that by tugging the tops up while twisting them around my calf. That almost gives a proper snug fit. Yeah, I have whomping size 11 feet, but I don’t have the mega mama calfinators to match. This adds one more reason to why I love to wear long skirts. They not only look good in themselves. They also compensate for a multitude of anatomical mismatches, dahling.
In my defense, when I talk about mixing black and brown, I’m talking very dark brown.
Fine, you’ve convinced me.
Now I simply must go out and buy more boots.
Look what you’ve done!
Brown is simply not in my color vocabulary. What I’m wearing right now is typical for me:
Black, black, black, purple, and black. You just can’t go wrong as long as you stick with black. Purple is the best color accent for black IMHO.
The problem with ankle length boots and knee length skirts is that the boots “cut” your legs off at exactly the wrong point, making them look stumpy. If you’re really tall with long, slender legs you can probably just about pull it off, but even then, there’ll be about a billion things which would be more flattering.
They’ll look much better with long skirts or trousers, imo.
Tossing my .02 in as I am a big calved girl with big ol’ feet (size 10 - 11ish depending of the material of the shoe). I’m also 5’9".
Personally, I’m a fan of pointy toed shoes. So what if I have skis for feet already? I find they make my feet look a bit narrower. For boots, I have primarily clunky platform stacked heel squarish toed boots that are mid calf and lower calf low heeled boots. I also have the calves to ankle issue and have found boots that are giving in that area- be they more of a stretchy material (like microfiber) rather than leather, or boots made specifically for a larger woman (since many tend to have smaller ankles to calf ratios anyways)
I will only wear the mid calf boots with skirts, and even then I want my skirt to be longer than the top of the boot. I know fashionistas say you can wear skirts shorter than your boots, but I’m not a fan.
And with regards to brown with black? Under most circumstances just say no. I can see brown boots with a mixed colored skirt and a black shirt, or maybe tawny boots with black skirt (as long as the shirt is white/buff/tan). But dark brown boots with black? Nope.
FWIW, I like boots from either Lane Bryant or Roamans, if I can’t find ones I adore in stores. These, for example, aren’t bad. However, [url=http://www.roamans.com/roamans/product/product.asp?pf_id=71182&dept_id=746&parent_id=742&]these[/url are more my style.
I have medium-sized feet (6 1/2 or 7) and muscular calves, therefore my boots are wrinkly around the ankles too. But I wear them anyway. Until I can afford to buy things that are cut specifically for my body (in other words, never), I’ll have to live with poochy boots.
Oh, and I love wearing black and brown together. I think they complement each other nicely. But then I think brown is even better than black as far as going with everything–YMMV.
Count me as another who prefers my skirt hem to overlap my boot tops. I like how Maastricht called it, a “country” look. I can’t explain why it pleases me so well, since I’m urban, but it just seems ideal that way.
<snerk> Yeah, but only if it’s thigh-high boots with a micro-mini. Preferably both in shiny white vinyl. That would look sooo Bond Girl. 
You would need to pack a gun to accessorize this look.
But seriously, folks, there’s a style of boot I love that I never see anymore. It must have gone out of fashion. Midcalf or so in height, made of thin, soft suede that’s all crinkled up and gathered at the ankle. It begs to be worn with a skirt that just covers the top, but shows the crinkly ankle which looks very attractive for some reason. Do you know the sort of boot I mean?
Ok, now I am confused. All you who say you have slouching - you all have it because your calves are big and your ankles are small? I have small calves and I get slouching too because my calves won’t fill out the boot completely and keep them up. So it looks like we are screwed either way!
I see knee-length skirts with boots all the time, the majority of the time you can see the top of the boot and I think it looks good, so I don’t think you have to wear a skirt that covers the top of the boot. Here’s an example of how I usually wear them:
Like this. With the skirt just above or at the knee and with the whole boot showing.
That’s how I wear them as well. I suppose it depends on your legs - mine are one of my better features, and I have decent looking knees, so I don’t mind showing them off.
I think the skirt over boot thing only really looks good on very tall women - on shorter gals it tends to look dumpy.
Ok, as long as I have all you boot-skirt girls in here, I am going to ask a question (hopefully the OP does not mind my asking in her thread). I just bought this skirt and I have black boots - should I wear tights or something with them or bare legs? Usually I wouldn’t wear hose with denim, but this is a little dressier I think than a regular jean skirt.
Also, would you wear that skirt to a class reunion or is it too casual? There is no dress code for the restaurant it is at or anything, but I want to look nice. Not overdressed either though. I want to look good in a “I just threw this together, and I look really good but I didn’t put on my best clothes for this either” kind of way.
I think bare legs are fine if you are wearing boots with the skirt. Since I’ve not been to a class reunion yet, I’m not sure if it’s dressy enough, but my instincts say yes, since it’s at a restaurant with no dress code.
Does your location of MI mean Michigan? Then I’d do tights, personally. It’s silly to see women go bare legged in cold-ish weather, even if wearing boots.
yes, I am in Michigan. I thought of the cold too, but really I just have to go from the car to the restaurant.
Maybe I should just wear a different skirt.
Or you could wear navy tights.
Of course not. The more boots, the better!
Linky no worky.
I like brown better than black for a neutral colour, for some reason. Perhaps because it’s more hippy than hipster. Wearing too much black makes me feel like one of those uber-cool assholes who hang out in Little Italy and sneer at you if you walk into “their” bar wearing a colour of some sort.
[confession]I wore the brown boots with black pants yesterday. Sorry, alice! I am so ashamed. The bright side is that I’m a civil servant so I was still one of the best dressed people in the building. And I only did it because I wanted to get started breaking in the boots, and I still have that new-clothes crush on the pants. It worked okay, I think, because they’re pretty light brown, not quite tan but close. I still wasn’t fully comfortable with it, though, and I promise I will never do it again.[/confession]
The link to the skirt doesn’t work. I’m assuming it’s a denim skirt you’re linking to, that falls above the top of your boot. I think it depends what you’re planning on wearing on top. If it’s a black chunky sweater, then boots, tights and a denim skirt is a really cute look. However, if you’re planning on wearing a lighter weight top, or a spangly blouse or something, the boot/tight look is going to be too heavy.
Hey, the skirt sold out! Well, it is a slim line dark denim skirt just to the knee. It has a little stretch and is very fitted and a little dressier than a regular jean skirt. I was thinking of wearing a lightweight merino wool sweater with it. I think you are right about the top, alice. I have been looking at other pictures online of skirts with boots and I think I am going to try it with black tights.
I am sure I will try it and several other things before I go. Now I have to find something for my husband to wear!
We should start a ‘put together an outfit for me’ thread where we can get advice. I am better at picking out things for other people than myself.