can pull off, but I’m really tempted to try. what do you think?
Dear HolyMama:
Seriously. What is up with you and the capitals?
As for the boots I think there are a few things to consider: How short is your skirt? What kind of boots are they (e.g., run-of-the-mill knee-high boots, Robin Hood ankle boots or, OMG, cowboy boots)?
- Short skirt/Cowboy boots: In your 20s? Go for it. You probably still have the legs for it and actually shave.
- Long skirt/Cowboy boots: Live on a ranch? Seems like a good idea where you live and you’ve seen people you’d actually trust wearin’ it outside the ho down? Then go for it. Besides, no shaving involved. That always gets my vote.
- Short skirt/Knee-high boots: Yes. You can totally do this no matter your age. Of course in your 20s the skirt can be above the knee. When you’re in your 30s or over "short skirt" can only mean "knee length" or you are going to crash and burn. Unless you’re Nancy Sinatra and then it’s just part of our national culture and you have standards to uphold–she must wear the short skirt. Or Tina Turner, because Oh.My.Word. she has the most perfect legs around.
- Long skirt/Knee high boots: Yes. Everything’s covered, no shaving. Heaven.
What’s that? What’s that you say? You say I haven’t touched on the Robin Hood boots? OK. Yeah, I totally think you should wear them with a short skirt. Take lots of pictures. Send them to me. I can’t wait to see the spectators’ faces. This ought to be good.

{ 10 comments… read them below or add one }
LMAO! Love skirts with boots. Short skirt with knee-high dress boots. Adorable! Come on, live a little!
YOU are the next fashion mavin! I’m looking to see you commenting on the red carpet fashions at the Oscars!
If I looked like Nancy Sinatra, I’d totally try for that look. Unfortunately, the “two pigs fighting in a blanket” look is out.
I’ve boots that are made for walking, but usually they’re walking with pants, not skirts.
the boots and skirt thing has always troubled me…so I don’t do it.
Nancy Sinatra, like wow. I have a complex now after seeing that picture. I think she could almost wear anything she wants and it would look fabulous.
thanks for the fashion tips, hoping to see more,
how about tips on how to mesh my land’s end mocs with just about everything. I love them, they are so comfortable. But they do look like clogs on my feet… the gauchos and mocs combo has me stumped, what do you do when it is too cold for sandals?? help me Chili, you are my only hope!!
HA, I am 25 and STILL haven’t attempted any boots with any skirts….I’m too scared I’ll mess it up…. I always spoof the “fashion trends”…
Back when I was in high school, I was all about the long flowy skirt and ankle boots. It’s scary, I know, but I thought I was totally cute. Never mind the blisters from the total uncomfortableness of said ankle boots… it was all about the Look! And we’re not going to even mention the Doc Marten boots. Ever. But oh, how I loved them. Seriously, there had to be something wrong with me.
You thought you had me, didn’t you? Well, I’m getting smarter. I finished my diet DP BEFORE checking your blog because I got tired of cleaning around my keys with a q-tip when your sassiness made me laugh. Sharp as a bowling ball, that’s me!
Now, the boots and skirts thing? Since I have calves the size of…well…CALVES, all my boots are sh-boots, or shoots, or shooties or whatever you call “boots” that just barely reach the ankle, and I wear them with pants. Or my bikini, cuz I’m an all-or-nothing kind of girl.
Oops! Did I just poke out your mind’s eye?
Sorry.
I love it!
OK so get this: The only time I ever wore boots with a skirt I was PREGNANT. And I looked HOT. And now those same boots will not zip.
But I have cute boys. But I have cute boys. But I have cute boys….
OH MY GOSH, YOU ANSWERED ME!!!!!
I LOVE THAT!!! (SORRY _ JUST CATCHING UP ON BLOGS TODAY AND WOOOOOOW! YOU ANSWERED MY SKIRT BOOTS QUESTION SOOOO WELL AND CURED ME OF MY CAPTITAL-Y STUFF!!! LOOOKEEE HERE!!!!!!!)