October 5, 2011

Today's Everyday Fashion: Booting the Problem

Fall is in the air, and as the weather turns crisp each year I struggle with one question: how do I wear my skirts in the colder months? My go-to shoes are usually a pair of pumps, and while there is always the option to add tights, those won't keep you very warm on a super-chilly day. That's why I immediately loved this idea of wearing slouchy boots with a pencil skirt! It's a little bit Western, still professional (for most work environments, always check your own dress code at work), and the best part is that this look can extend the life of your skirts so you can wear them in the winter! Tell me - do you wear skirts in the winter? What are your favorite tricks for weather-proofing skirts during the colder months?

Inspiration photo: New York & Company
Shirt: Ralph Lauren Outlet, $20
Skirt: Limited, $25
Belt: Gap, $40
Scarf: c/o Happy Scarf
Boots: Bakers, $90 (similar)
Necklace: Westminister Abbey gift shop, $35
Watch: Michael Kors, family gift

1. Chinese Laundry leather boots, $120
2. Old Navy navy pencil skirt, $29.50
3. Forever 21 double buckle belt, $8.80


  1. I love this idea! I was actually worrying about all the skirts in my closet getting lonley this winter and hadnt occured to me that this might just solve that! I might throw in some tights or fluffy socks as well!


  2. I wear Under Armour underneath my tights!

  3. love the look!!! :) the scarf is pretty and out with boots..gotta love the fall looks! :)

    xo Nav

  4. Cute look! I love that scarf! I've never worn a scarf like that but I like the look! And I'm actually wearing boots and tights with a dress today! I'm kind of picky about what boots I like with skirts but sometimes it really does work best and makes it a little more casual!

  5. That scarf is amazing tucked into the belt! So impressed. I chicken out of winter skirts and skirts in general but I want to try something with these grey tights I've had for forever from F21 that I've never worn - any suggestions? I don't have many skirts so I'd prob need to invest in one but the one you have on looks like  a nice universal option. But gah I'm obsessed with the scarf under the belt.

  6. Thanks Caitlin! I'm loving gray tights for fall this year. They are on my wish list and I plan on posting some outfits with them as soon as I find some!

  7. Sweater tights are a great suggestion! You could also add some leggings to an outfit like this in really cold weather!

  8. I have started to amass more great colors of tights or i just wear boots and tough it out!  Welcome to boot season! its going to be awesome!

  9. Ha, I missed your post yesterday but great minds think alike because I just wrote about transitioning skirts into fall on my blog last night! I am loving this outfit, you always look so great!

  10. Amazing outfit. It looks so perfect on you. I love those boots they are so pretty.

  11. I always wear skirts in the winter! My trick is to wear leggings over pantyhose or thick tights, depending on the look I'm going for. Then I can wear any shoe I please! Here in northern Europe pantyhose is a must. In fact, people think you're tacky if you're not wearing any (exception if it's 80 degrees outside)! Funny how it's the reverse in the US. However, pantyhose has really grown on me over here and it can be very elegant. 


  12. I love your style! I've always loved fashion and your blog has helped inspire me to start my own blog up and do something with my passion for fashion.

  13. Thank you so much Amber! :-)

  14. Caitlin, that IS funny! Totally adds some insight into why Kate is always wearing them now (that, and I heard it's required by the royal court sometimes?). Pantyhose = big no-no in the US, but tights are everywhere of course!