Tuesday, October 27, 2009

How to wear Boots with Skirts/Dresses

If there are many (or any) boy readers, I apologize. I got an email asking for clarification on the rules for wearing boots with skirts to work. I have to admit, this is something I always wonder about when I'm about to attempt it! But, during the colder months, boots and pants/boots and skirts/boots and dresses---it has to happen!

I think it's totally fine to wear boots with skirts. It's just a fine line between looking like you're going skiing and looking like you're going clubbing...personally I'd rather be accused of the former.

So, some rules, please?
*Keep in mind, there really aren't DEFINED rules...or at least ones I could find..I will be doing more research and will let you know if I come upon them!!

1. Own a pair of classic boots. Not too trendy or too "one style" (such as western). These can be either flat or heeled.
2. Preferably, own a black and a brown pair :)
3. The boots should come no higher than to the knee (I know over-the-knee is in style but probably not the best for work...or for skirts!)
4. The skirt or dress should not be longer than the boot is tall (in my opinion...too covered!!)
5. Own some fun tights. I love JCrew's tights, but I limit myself to either buying them on sale or to purchasing one new pair a year. I wore a herringbone grey/black pair to death last year, so that will be my purchase this year.
6. Skirts should be your normal work skirts (twill, wool, dressier jersey, etc) and can range in lengths. I have some pencil skirts with a back kick split that I would easily wear with boots, or even a slightly shorter skirt or dress that, with tights, would work great! I think the trick is that if it is a slightly shorter skirt or dress, the tights make up the difference and keep you from looking like ... anyways ...
7. Keep the outfit from looking equestrian -- don't make the whole look morph into a costume!
8. Denim skirt...I'm not sure what the exact rules are, nor could I find anything, but I think you have to hold fast to rule #7, and if this skirt is going to work, it should be more of a dark dressier stretch denim, to the knee, than a cut-off frayed denim from Abercrombie that would be better for a Kenny Chesney concert with cowboy boots :)

Now, I have a pair of black boots that I wore all winter long last year with skirts and dresses. I have this one jersey dress that has ponies on it and I wore the two together a few times. It was like a play on words because I didn't LOOK like an equestrian, but because the dress had ponies on it, it was like a play on words outfit...

Top trends this year??
OOoooh I love them..the booties with tights, skirts/dresses...the t strap shoes/Mary Jane's with tights and skirts/dresses... Here are my favorite examples!

(c) The Sartorialist
More great work options!



Banana Republic

If she can do it, you can do it...so DO IT! :)

(c) The Sartorialist


  1. Awww !! your advise is precious as always :) and that skirt & boot length tip was very helpful.

  2. Love your post, Ann. I actually chose to wear a dress similar to the grey JCrew one your showing above with a new pair of boots I bought today to work :)...(My first time)

  3. I inspired myself to wear a sweater dress and boots today :)

  4. Great article Ann, Thanks!!!! ;)

  5. I think I did ok on Friday... was not work so it was a little edgier...

  6. Thanks for the great info!

    My problem is I have thick calves. Call it big-boned, call it fat... I'd love to be able to wear some boots with skirts but I usually run into two issues:

    1) Most boots' circumference (with the exception of those Ugz or whatever they're called) is the same size or smaller than my calf and therefore squeezes it. The result looks like my calves are being choked... well, maybe not THAT bad but bad enough where I feel uncomfortable.

    2) My legs are stubby :( Maybe it's insecurity or the notion of trying to look like one of those models but it doesn't look right on me.

    Anyway, enough. Great post :)


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