Skirting the Issue – Part Un

Une femme’s relationship with skirts has had its ups and downs, and I’m not just talking hemlines. I love the idea of them, but the execution is at times problematic.

As a child, I was mostly put into dresses instead of skirts, as my mother believed that dresses were more slimming. And I hated that feeling of a blouse coming untucked. In college, I sewed myself a blue calico wrap skirt that I wore almost every day with a Mexican peasant blouse (and a sweater in the cooler months) for a year, being too broke to buy any other clothes. The 80’s and early 90’s were the era of the long broomstick skirt with a tunic length top over, and I’ll admit to having embraced that trend, again believing it was slimming. But in recent years, une femme has not been a great enthusiast of the skirt. Anything requiring the wearing of pantyhose (I do not go barelegged except for the occasional weekend capri pant) was just too much trouble and required too great of a sacrifice of comfort. But since last year, my position has softened a bit, thanks in part to Spanx, in part to discovering that even a short, curvy femme can rock a pencil skirt, (thanks again to the late, mostly great Forth & Towne) and in part, to inspiration like this:
Photo: The Sartorialist

I really love this fuller silhouette (and the pocketses, preciousssss!), and recently purchased a similar style from J.Crew. At $1800, the original was a bit trop cher pour moi. When the J.Crew version arrived embellished with some ungodly huge-and-ugly beltloops, a trip to the tailor to remove them was the first order of business. In experimenting with how to wear it, I quickly determined that Ms. Herrera’s look above did not work for me, being too busty and short-waisted to carry off a tucked in white blouse. But once I’m a bit more mobile, I plan to try some other combinations, most of which will probably involve some iteration of a black top.

Owning a great pair of knee-high boots has also been an impetus to get me back into skirts. It’s tough to go wrong with a skirt/boots ensemble, and the look is really timeless. But I’ve also recently been tempted to try ankle boot with skirts. Next up: is there a way to wear this look without making one’s legs resemble tree trunks?

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  1. As someone who is 5’2″ and (ahem) definitely curvy, my answer to the “tree trunk” issue is black tights, black pumps or ankle booties or black knee length boots. And, you may not feel you can “rock” the white blouse thing, but perhaps a dark blouse in forest green or burgundy or purple (you’re either a purple person or you are not…I am not but it works for a lot of people)or even a dark rust might work.

  2. Good suggestions, thanks! Being a redhead, I’d go for either a forest green or dark purple. I think the key is going to be keeping the top dark, and close fitting.

  3. I love Carolina’s look. I think her photo illustrates how it’s all about the shoe. A sexy shoe takes keeps it current for an over-40.

    I’m 42, almost 5’5, and shortwaisted. As much as I love them, tucked in shirts aren’t good for me either, and I think I have to leave the ankle boots for other people.

  4. One of these days I’m going to figure out the skirt-boot thing. I know my husband would like it. I’ve always had a hard time finding skirts I like.

    As for ankle boots with a skirt – I’m pretty sure it wouldn’t work for me – I don’t have thin enough legs and since I’m fairly tall at 5’9″ – I would look like I’m walking around on a couple of 6×6’s. LOL.

    I also think I’m more of the “pencil skirt” type. But I might be wrong about that. Time to start trying on different things I guess and see how it works.

  5. I’m just not a fan of the ankle boot and skirt/dress combo. I think it makes everyone’s legs look short. A shoe and tights in the same color would definitely help the situation, though. Black is obvious, but what about gray?

  6. I’m 5 foot tall and always have had a passion for ankle boots and skirts. I prefer no more than a 2″ heel for mobility – I walk miles – and I think the key is to select styles with the ankle “built-in”, in other words a structured contour. Makes you look like you have ankles under there whether you do or not. I wear them with tights but also shaded hose or some sort. I feel coltish in them, imagine.

  7. Ankle boots can work on short people! So long as it cuts below your ankle bone (a shoe-boot), or if it is slit or otherwise cut down in the front, exposing a sliver of the top of your foot, it acts to visually lengthen your leg – even if your tights are not the same color as your boots. Dark plum or wine tights contrast nicely but subtly with black of dark brown boots. Go play – it costs nothing to try on!

  8. I have piano legs (AKA “cankles”), so no ankle boots! Since I love skirts, I wear black tights with a shoe with a slight wedge like the Taryn Rose Kelsey.J Crew has some lovely thinner sweaters in Egyptian cotton that work well with skirts.

    Also- you might try a white blouse worn on the outside, ending just below the waist, if it is finished well, like Anne Fontaine’s.