Fashion question - boots and skirts

So today I went out looking for a pair of knee-high boots to wear with skirts. Of course I couldn’t find any (not that I’m bitter), all I could find was a pair of amazingly spectacular short boots which I fell instantly in love with.

This will give me TWO pairs of short brown boots and no knee-high ones.

My question: can I wear them with knee-length skirts? They always look stupid to me when I try them on, but my taste is notoriously unreliable.

Depends on the tights you’re wearing. With black or brown tights, yeah, it’s okay. Flesh-colored [erm, if your flesh is neither brown nor black] tights, no. Other colors – depends on what color the skirt is.

It really depends on how tall you are and exactly how tall the boots are. As a general rule, I wouldn’t do it.

However, I have seen girls around here that pull it off because,
a) They are short. No taller than 5’3"
b) The boots cover over half of their calf

What is the shape/style of the short boot? Is the skirt flared or straight? Short boot with knee length skirt is fashionable right now but whether you’re comfortable with the look is the big question!!

Wow! thanks for the quick answers. I see I’m not the only one with boots on my mind …

really? Brown boots, black tights?

… does that mean I can wear them with black pants too?

(Please forgive my enormous ignorance on the subject. I’ve only recently started dressing like a woman.)

I am about 5’9" and would be 6" with the boots.

I like my boots chunky (a product of having enormous feet) and my skirts flared or A-line. What difference does it make? I mean, I could go get a straight skirt if I had to …

This is a great question. I can’t bring myself to wear short (lower than just below the knee or mid-calf) boots with skirts. Some women can pull it off. Usually with a pair of funky tights or fishnet type hosiery; these women tend to be the more adventurous, the more punkish among us. It’s a tough look to pull off, though.

Also, what size/shape are your legs? Gals with heavy legs tend to look awful in short boots paired with skirts.

When in doubt, wear them with pants.

Keep in mind, I recently horrified my Doper Sistren by saying that I’ll wear a red turtleneck with a purple sweater, so YMMV, etc. –

But, yeah, I’ve worn black tights (a staple of my wardrobe) with a brown dress, and also with brown shoes – depends on the rest of the outfit, though. I have one skirt that’s tan, black, and touches of dark red – I’ll mix black and brown with that. I’ve also got a couple of sweaters that are brown, tan, charcoal, etc., mix.

Hm. This is all very interesting.

I’ll have to give it a go and see if my husband laughs at me. This is my strategy of last resort - although he has never learned the key lesson of “never laugh at your wife’s fashion experiments,” I often find it very helpful because he has much better taste than me. Unfortunately he won’t come shopping with me so it’s always trial and error.

It’s just frustrating because I have this awesome pair of black pants, and a lovely black skirt, that I really wanted an awesome pair of boots to wear with. I already have awesome short brown boots, and brown shoes, and black shoes, and I decided exactly what kind of black boots I want, and all I can find is more and more pairs of short brown boots I want to buy.

What, are rounded toes and stacked wooden heels not in this season? Or are they so “in” that the stores I go to, don’t carry them? Argh.

Maybe I should just go buy more brown pants.

And move to a place with a bigger closet :rolleyes:

It’s hard to comment without seeing the boots & skirt modeled. That said, it’ll depend on the boot, really. For example, biker boots would look good, I’m guessing. But you’ve got 3" heels on the boots, I’d have to see 'em to know.

I just bought some great black tall boots from DSW and they had two big aisles of them, all kinds - tall and short, pointed toe and round, pointed heel and chunkier. Most of them were less than $100, compared to most places I checked I thought that was a good deal. Do you have one in your area? It does appear that the more pointed toe and heel are more in this year though. I have some older black boots with a chunkier heel and rounded toe and they don’t look as sophisticated or dressy as my new ones with a less chunky heel.

I personally would not wear a short boot with a skirt, but they look good with pants. I am just a little taller than you.

I am actually having more trouble finding skirts I like to go with them! Everyone now has those peasant and frilly layered skirts and I like more tailored things.

Actually, they look quite a lot like that, except they’re shorter (just above the ankle), light brown, with a big heel and no buckle. Also there’s about an inch of platform so they really are enormous.

And I must say I’m disappointed, I clicked the “Cowgirl and Western Boots” link on that site and didn’t find anything that suits me. Perhaps I should change my username. Round Toe Stacked Heel might suit me better.

Velma, I don’t know what DSW is so I guess they don’t have them in Canada. Sigh. If only I had the guts to buy boots online, my options would increase substantially.

The problem with the pointy toes and skinny heels is that I think that shape looks goofy on a body like mine: long, wide feet (so pointy toes mean I usually have to buy even longer sizes, which of course are subject to availability) and cyclist’s calves. Last time I tried I couldn’t find any that fit both my calf and my ankle, let alone fit onto my foot without looking like a clown shoe. I find the chunky styles are more forgiving in this regard.

Hmm, cowgirl, enormous feet, only recently started dressing as a woman… sounds just like me.

For a cowgirl, as long as your skirt has that white eyelet lace trim at the hem, you can wear any length skirt with any sort of footwear. But for the life of me I just can’t picture you in anything but cowgirl boots! Tooled Mexican leather, the whole works. Seriously, hon, I bet you look totally hot. I agree with twickster’s preference for black tights to go with that combination.

Eastern urbanite Johanna, whose boots are knee-high black suede and only worn with long skirts.

Well, I just went and bought them ($40 - hooray for working above a Winners!), and when I was there I gave the knee-high black boots the old college try.

And … the ankles don’t fit. They’re always “slouchy” whether they’re intended to be or not. Seeing as the rest of me is somewhat oversized I’m surprised that my ankles seem to be smaller than the average size 9. I guess it’s a look I’ll have to get used to. How do the rest of y’all find the ankle part of knee-high boots?

I didn’t notice before that my new short brown boots are almost exactly like my old ones. I’m noticing a trend here … they’re both round-toed, with a stacked heel. It’s just that the old pair has holes in them and they’re badly scuffed up, and the new ones are a somewhat different colour (they look sort of “natural” or “distressed” rather than dyed) and make me a whole inch taller.

I think I need to broaden my horizons. Meantime, I need more brown pants.

According to this survey, 26% of people say it’s okay to wear brown shoes with black pants. I’m not entirely convinced.

Johanna, thanks for the props! It was actually your Payless-four-inch-heel-boot thread that inspired my current boot hunt (although I struck out at Payless, all the boots in my size had short and nasty heels.)

In fact I am much more of an urban cowgirl, and my mount is of the two-wheeled variety. Unfortunately clothing made for this kind of rider is usually butt-ugly.

My wardrobe is largely based around flared pants but I do like me some knee-length skirts. One (a beige cordouroy one with an uneven hemline, it comes down in a point in the front) I think will go quite well with my new boots, I just have to find the right tights.

I also have big feet (size 10, US) and I love boots as well. I have a super fun pair that is hot pink faux ostrich skin with hot pink rhinestones. Way fun! Do a google on Justin boots and you will find all kinds of fun boots, in fun colors and regular colors and they fit! Also I have had them a year and only one rhinestone has come off!

Barrels

DSW either stands for Designer Shoe Warehouse or Discount Shoe Warehouse, I forget which. Here they are but it doesn’t look like they are in Canada.

I have size 8 1/2 to 9 feet too so I don’t like the super pointed toe either but I found a tapered toe works fine. I did have to try on a few to get ones that fit my calves well too (I probably have the opposite problem, boots tend to slouch or hang off my calves). Do you have Marshall Field’s in Canada? They have lots of boots out now too but they are a little more expensive. A good pair of boots will last through the years though so I can convince myself it’s worth it.

You really would have tons of options if you shopped online, maybe order a few pairs and send the ones you don’t like back?

DSW either stands for Designer Shoe Warehouse or Discount Shoe Warehouse, I forget which. Here they are but it doesn’t look like they are in Canada.

I have size 8 1/2 to 9 feet too so I don’t like the super pointed toe either but I found a tapered toe works fine. I did have to try on a few to get ones that fit my calves well too (I probably have the opposite problem, boots tend to slouch or hang off my calves). Do you have Marshall Field’s in Canada? They have lots of boots out now too but they are a little more expensive. A good pair of boots will last through the years though so I can convince myself it’s worth it.

You really would have tons of options if you shopped online, maybe order a few pairs and send the ones you don’t like back?

Oops, sorry for the double post, that is happening to me lately. And now I see that we actually have the same calf problem, I assumed cyclist calves meant you were muscular and having trouble b/c the boots were too narrow. I get the slouchiness too, and I have space between the boots and my ankles. This time I shopped for some that had a firmer shaft (inset your own joke here) so they stay up better (and another joke here). The pull on stretchy kind don’t work for me b/c they don’t cling to my calves to stay up so I need boots that can stay up of their own accord.

Can you tell I have been thinking a lot about boots plus skirts lately? I am trying to put together an outfit to wear to my high school reunion so I have been all over the place shopping.

Mmm, boots. I just recently indulged in some boots. They’re rather of a different sort, but I have the same problem of gigantic calves and tiny ankles, further complicated by feet that are between UK sizes (why don’t they do half sizes?!). I wear skirts all the time, but most of them are long so it’s not so much of an issue for me. Also, all my clothing is grey or black, so I can’t really advise on the brown/black thing. Ah, the pleasure of a monochromatic wardrobe!

You can’t wear those boots with a skirt, I have hereby declared. Your feet will look like cartoon PowerPuff Girl feet, which is fine if you’re a 15 year old Hirajuku girl, but absurd if you’re anyone else. I mean, REALLY absurd.

Wear them with jeans, or casual brown pants. Do NOT wear them with black pants or I will cry like a little girl.

Ok, I’ve had my say.

:: golf clap ::
Seconded.