Boot season is almost upon us! (Actually it is already upon those of us who believe that open-toed shoes shouldn’t be worn after about September 5. Meaning me. Yes, I am an odd duck.) Boots are a key element in most womens’ fall and winter wardrobes, and a pair exists to complement nearly every look.
But as versatile as boots are, they can be incredibly unflattering if paired with the wrong skirt or pant. With the popularity of Uggs and cowboys and slouchy boots and other styles that essentially fit our legs like contour-free cylinders of leather, whipping up an accidental set of artificial cankles is frighteningly easy.
So let us review the guidelines for flattering boot wearage before the cold really sets in!
Here’s a bit o’ info you’ve heard me say about eleventy gazillion times: It is unbelievably important to broadcast the presence of your delicious womanly curves in order to achieve maximum figure flattery. This is true of shirts, skirts, coats, pants, essentially all garments. And if you allow a set of curves in one sector of your body to be masked, you can generally offset that masking by wearing something more fitted elsewhere: Wideleg pants look best with a fitted top, and a voluminous sweater can still be sexy if paired with a sleek skirt.
Turns out these rules apply to boots as well, since they affect perception of our lower leg curves: Ankles and knees.
You take your ankles for granted, don’t you? You’re thinking, “C’mon, Sal, EVERYONE knows we’ve all got ankles. Do we really have to define them for the casual observer?”
YES YOU DO. Meet my Frye Campus boots. I adore them in their clunky, banged-up glory. But they are built like grain silos and among the least flattering shoes I own. Paired with this mid-calf skirt above, for instance, they give me mad artificial cankle. Below you’ll find the long view. (With apologies for decapitation. The combination of fright-wig hair, demonic red-eye, and super shiny night-face would distract the hell out of you, so I chose to crop.)
So we’re starting with the worst possible combo, here. The skirt falls mid-calf, which is an unflattering spot for anyone who isn’t a supermodel: By hitting the calf at its widest point and hiding the knee (where the leg narrows), a skirt of this length gives the impression of completely curvless legs. Additionally, the boots mask my ankles, another missed opportunity to define my womanly form for the observer. And here I’m wearing a loose top, which does nothing for my torso’s curves either! Triple whammy. You can hardly tell what my body looks like at all. I could be Twiggy or Oliver Hardy for all you know.
THIS is how I actually wear my sweet little spotted skirt: Fitted top and fitted knee-high boots. Neither helps with the calf flattery, but at least my waist and ankles are both defined, giving some impression of where the real me is hiding under all that cloth and leather.
Another fall boot-wearing style that I can hardly wait to sport is cropped cargos with tall boots. And yet …
… gotta watch it! Here’s another pairing that creates cankles where, in real life, there are none. The cropped pant hits me in the same spot as my skirt up above: Mid-calf. And since the Fryes fail to define my dainty little ankles, we’ve got some major tree-trunk leg going on, here.
So what the heck CAN I wear with my beloved Fryes? And what can you lovelies wear with any fabulously fun fall boot that fails in the ankle definition department and hits your leg at near-knee?
A miniskirt is your absolute best option, if you’re comfortable wearing one. I know minis are bit revealing for some of us, but bear in mind that in a month or so, tights will be seasonally appropriate. Tights with a mini is a lot less scary than bare legs with a mini, no? In any case, since a miniskirt falls well above the knee, you can see how the entire leg is shaped. Doesn’t much matter that the ankles are hidden. Here, I’m in the optimal mini-and-fitted-top combo, BUT …
OK, but miniskirts have limited application. What else can be worn with ankle-obscuring footwear?
Not much, kittens. In my opinion, your only other option for a knee-high, cylindrical boot is untucked pants or jeans. Doesn’t show much of the boot shaft, of course, but is still cute and flattering.
The problem with stuffing your jeans into a pair of Uggs is that they both mask ankle curves and often reach so high on your leg as to mostly mask your knees. No ankles, no knees, no optically identifiable lower body curves. Even the slenderest of willowy college girls can be made to look 10 pounds heavier if she sports this look.
If you’re hell-bent on jean tuckage, here’s what I’d recommend:
- Boots that taper in at the ankle, like my fitted knee-highs or granny boots pictured above
- Boots that hit mid-calf or lower, paired with slim-fitting jeans. A shorter boot paired with jeans that show off your calf-to-knee-to-thigh ratio can be really cute, and is far more flattering than shoving your jeans into knee-high ankle-maskers.
Hope this was helpful! For more photo-heavy how-to’s, take a peek at:
Know Your Necklines
Skirt to Leg to Shoe Ratio part 1, part 2, and part 3
How to Look Awesome in a Photo part 1, part 2, and part 3
Universally* Flattering Styles part 1 and part 2