asked and answered: what to wear with leather?

Yay, reader question! Being answered in a timely fashion! I’m pretty proud of myself. Amy asked such a great question over the weekend, I had no choice but to answer straightaway:

All the leather out there reminds me of my unresolved question from last fall: how do you match leather tops/skirts to boots? Do we avoid leather boots completely? Do the boots need to match the color of the leather top/jacket/skirt? If not boots, then what kind of footwear, especially in the colder months? Thanks! ~ Amy

Amy, you’re so not the only one wondering about this. Matching leather is a hurdle it took me years to master – and finally, I realized I was worrying too much (as usual). In general, the only rules I stick to are these:

  1. Too much of any one color leather is a bad idea, unless you’re Courtney Love and it’s 1992. So, I’d say avoid tall black boots with a black leather jacket and a black handbag.
  2. Black mixed with chocolate brown is my worst nightmare. Just don’t. 

Beyond that, I think the sky’s the limit! Black leather jacket and black heels? Sure! But you could also do tan ankle boots, a bright flat or a bold-hued heel. Don’t force yourself to match, but don’t fight it either.

So, those are the ground rules. But the leather skirt is a trickier problem. For me, tall boots with a leather skirt is a little too “Sunday morning walk of shame”. My general rule is that if I’m wearing one overtly va-va-voom piece, that’s plenty. For a leather pencil skirt, I’d stick with heels. (I’m the biggest heel-phobe ever, and even I won’t wear a pencil skirt with flats.) A low heel is fine, but look for something with an ankle strap – it nods to the sex appeal without being over-the-top. And for heaven’s sake, no tights with ankle-strap heels. I know, this doesn’t bode well for winter. Fashion is a cruel mistress sometimes.

Shoes for a leather skirt, via shopping's my cardio

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If your leather skirt is an A-line or flare? I’d still pair with heels, especially if the skirt is black. But you do have more options. I love this paired with a demure d’Orsay heel – keep the height low so the look is playful.

Shoes for a leather skirt, via shopping's my cardio

1 / 2 / 3

Now, if you break out of the black leather box and go for something with color, you open up a whole world of options. A lighter color tones down the dress factor and the severity, so you have room to play. Ankle boots definitely work here, if you have the height for it, or give a pair of smoking loafers a try. It’s the perfect way to make this style work for more casual fare, especially if you add a little extra preppy up top: maybe a cashmere sweater layered over a button-down and a great statement necklace.

Shoes for a leather skirt, via shopping's my cardio

1 / 2 / 3

Anyone have more advice for Amy? Leave it in the comments. It takes a village, friends.

Got a burning fashion quandary? Hit me up! Twitter, Facebook or good ol’ email: editor {at} shoppingsmycardio {dot} com. I’m here to help!

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7 comments on “asked and answered: what to wear with leather?

  1. A

    I love my biker-esque black leather jacket with both gold heels (today) and black low-top Converse (the more beat up, the better). I think I also did purple suede heels and a grey jersey dress with it once, too. So far, have worn my cognac leather skirt with opaque black tights and black booties, but I think I will also venture into knee-high black boots with a flat heel. I think my purple suede heels would make it look pretty fab, as well.

  2. shoppingsmycardio Post author

    A: Love all of these options! I think the cognac really does open up more possibilities, probably because it’s more casual than the black. And I’m definitely on board with the purple suede!

  3. lpm

    Thank you for these tips! I bought that A-line leather skirt, and I will be paring it with heels.

  4. Sarge in Charge

    I completely agree with your rules. A leather skirt (even a more demure one like the bottom option) is just so “bad girl” that you need to go more “good girl” with your shoes. I have one very similar to that last option and always wear it with a pretty demure shoe, such as loafers or Rachel Comey Mars ankle boots. I love the cognac color because it is great with just about anything, no need to worry about matching leather.

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