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.

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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.

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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.

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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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