Earlier this week I sent a letter about what shoes go with your pants - we looked at straight leg cropped jeans, kick flare pants, wide leg jeans, wide leg trousers, and pajama style pants. It was a lot (read it here). At first I thought I’d include skirts in with that send but then….it was a lot. So here’s part II, as promised - what shoes go with your skirt.
A MIDI SKIRT
A midi skirt, especially one that’s kind of flared, like this one, is pretty easy in terms of shoes. You want the skirt to hit mid-way between your ankle and your shin, though the camera angle here makes this one look longer. It’s pretty and ladylike with a dainty heel…. This coat is from The Row (try this one too), the shirt is thrifted (but I like this one and this one), the skirt is The Row, and the shoes are ancient Saint Laurent, but these do something similar. Oh! And the feather brooch is Indress, of course.
Or more masculine and clompy with knee high riding boots. Try these riding boots.
Ok, this is a screenshot I took of the video, which is why I look so crazy, but this also works super well with little sneakers.
It DOES NOT WORK with ankle boots (even though these are gorgeous and heaven). You need the boots to either go all the way up to your knee, or to not be boots and be shoes instead. This cuts your leg off at such a weird place and does nothing good for your leg, the boots, or the skirt. Ankle boots + midi skirts = X
If you lose the jacket, you can wear it with loafers (also love these loafers), or ladylike flats (I prefer loafers to keep it a little more tomboyish and not so sweet). You want the skin of your ankle and shin to show so that it lengthens your leg.
A cutie pie minimalist sandal also works here (but not with the coat, too off balance), it makes everything feel very low key and casual, and again, makes your legs look longer. The only thing that DOES NOT WORK!!!!! Does not!!! Is an ankle boot that doesn’t go all the way up under the skirt. It will likely cut your leg off at a very unflattering point, and just looks kind of unintentional and half-baked if it doesn’t go all the way up under the skirt and cover all of your skin. You either want to show ankle, or cover the whole shin. Those are your choices.
However, ladylike skirt with lady shoes….no good. Too obvious and too frumpy/Gossip Girl.
It works with heels, but this is a very specific vibe. To me feels a little too on the nose…. it’s sexy as hell, but for my style, a little too retro I think.
However knee-length skirt + riding boots? CHECK CHECK CHECK! I love. Very classic. Ankle boots are also X here, I explain why in the video.
MINI SKIRT
My goodness I love a mini skirt. This one is Tory Burch. My blazer is an old Dries men’s one. The length works with almost any shoe - the ladylike flats look great. I think because the skirt isn’t frilly or ruffly, it’s more graphic, it doesn’t skew too lady with these bow pumps.
Loafers or riding boots - also GREAT GREAT GREAT! Loafers + mini skirt = horny boarding school, which is my favorite thing.
Sneakers are also CHECK! I wish these were darker, but it is what it is.
However ankle boots…no. Again, no. Does something weird to your leg and is neither here nor there. It looks unbalanced to me. Heels I would also say - proceed with caution. It is a very SEXY look!!! If you’re going to do it, choose a heel that’s a little more offbeat and intellectual than kinky - unless kinky is your thing in which case, hell yeah, girl.
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