My Own Personal Style Challenge: 1 Faux Leather Pencil Skirt, 8 Ways

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Hi friends! Back to the basics today with a little shop-your-closet inspiration post that was honestly so much freaking fun to put together.

1 Black Faux Leather Pencil Skirt, 8 Outfit Ideas

I’ve owned this black faux leather skirt for a few months now, and I while I LOVED how it looked with all of the sweet sweaters and blouses I styled it with in-store (I picked it up at a fave local boutique here in Half Moon Bay, Crow’s Nest), the second I got it home, it immediately felt…intimidating. Overkill. A lovely option for date night, maybe…but even pulling it out for that pushed me a bit out of my comfort zone.

BUT…I’m taking off for Vegas in a couple of weeks, and if Vegas isn’t an excuse to bust out a leather skirt — faux or no —, I’m just not sure what is. So one afternoon I took the time to play around with a few options that felt more…me, and I liked the results so much, that, well….here we are. First off, a few notes:

  1. Obviously, I’m working with a leather(ette) style here, but I feel like most of these outfits would work just as well with a classic pencil skirt in a somewhat playful fabric, or even a knit pencil skirt. (Specifically thinking of this one from Free People, which a few of us also own and love.)
  2. I couldn’t find the exact skirt I’m wearing in stock online, but I’ve linked up quite a few below. This one is an exceptional dupe (and available in plus sizes, too), but this pull-on style looks so easy to wear and gets stellar reviews across the web (available on Amazon, too).

K, here we go!

1. Brunch Meets Business Casual

A shop-your-closet, minimalist wardrobe inspo with a black faux leather pencil skirt. Styling it up for everyday, date night, business casj & more — 1 midi skirt, 8 outfit ideas.

Pencil Skirt (similar) // Chambray Shirt (TTS) // Black Pumps (TTS) // Trench (TTS)

Popping this up top because it was hands down my favorite look of the bunch, and it was one of the last ones I put together as I was folding a basket of clean laundry that happened to hold this shirt. Something about the chambray here just lends such a sense of ease…and for a business casual version, you could tuck the shirt rather than tie it. Of course topping it off with a chic, easy trench lends a cool, collected vibe.

2. Date Night – With A Formal Twist

A shop-your-closet, minimalist wardrobe inspo with a black faux leather pencil skirt. Styling it up for everyday, date night, business casj & more — 1 midi skirt, 8 outfit ideas.

Pencil Skirt (similar) // Tie-Neck Blouse (runs large; order one size down)
Black Pumps (TTS) // Blazer (similar)

I just picked up this top in hopes that it would inspire Chris and me to lock in a solid plan for Valentine’s Day. And while we’re no closer to having reservations booked anywhere special (yet!), I am solidly in love with this blouse. I think the key to keep this from looking too vampy is the coverage here. Don’t get me wrong: this would look pretty damn sexy with my favorite little cami bodysuit, but again I feel like that pushes this outfit more into the territory of something I would chicken out on about 2 minutes before leaving the house. Adding the blazer to the high-neck top turns this into an outfit I’d even wear in a professional setting. (Oh hiiii, tradeshow days of my past.)

3. With A Sweater + Booties, a.k.a. The Easy One.

A shop-your-closet, minimalist wardrobe inspo with a black faux leather pencil skirt. Styling it up for everyday, date night, business casj & more — 1 midi skirt, 8 outfit ideas.

Pencil Skirt (similar) // Sweater (TTS) // Black Booties (TTS)

A total no-brainer of an outfit that would see you through all sorts of occasions: a workday, a school function…church? (Huge question mark there — I can’t even pretend I know what folks wear to church these days.) This is more or less the way I envisioned wearing the skirt when I took it home — and for good reason. It works.

4. You Knew There’d Be A Graphic Tee

A shop-your-closet, minimalist wardrobe inspo with a black faux leather pencil skirt. Styling it up for everyday, date night, business casj & more — 1 midi skirt, 8 outfit ideas.

Pencil Skirt (similar) // Graphic T (TTS) // Tan Booties (TTS)

Now we’re talking. I consciously paired this with a darker graphic tee because I feel like the monochromatic thing actually takes the edge off the skirt a little. (It would be awesome with a lighter or brighter band tee, too but the whole look would just draw more attention to itself.) I resisted the urge to go with black booties here, and I’m digging it. The lighter color is a bit more elongating and elegant. Would top this with an oversized, menswearish blazer or a car coat for drinks or a night of live music.

5. Dressed Down, Part 1

A shop-your-closet, minimalist wardrobe inspo with a black faux leather pencil skirt. Styling it up for everyday, date night, business casj & more — 1 midi skirt, 8 outfit ideas.

Pencil Skirt (similar) // Adidas Tee (runs small, order 1 size up) // Sneakers (TTS; also on Amazon) // Trucker Jacket (TTS)

I was so pleasantly surprised to find that this actually worked, because this is as close to my weekday uniform as it gets. (Read: absolutely within my comfort zone.) I would very realistically wear this to the playground, to the grocery store, to swim lessons (ok, maybe not to swim lessons because it is muggy AF in there and NO ONE should be wearing pleather in those conditions). You get it. I could see swapping out the trucker jacket for a long cardi, too, to add some softness.

6. Dressed Down, Part 2

A shop-your-closet, minimalist wardrobe inspo with a black faux leather pencil skirt. Styling it up for everyday, date night, business casj & more — 1 midi skirt, 8 outfit ideas.

Pencil Skirt (similar) // Sweatshirt (TTS) // Sneakers (TTS; Left, also on Amazon)
Mules (TTS; Right) // ALLSAINTS Leather Jacket (runs small, order 1-2 sizes up; fully-stocked!)

Ahhhh, another outfit that I would wear all day long (and I did! It’s actually the one I wore the remainder of the day when I wrapped up these selfies). The only thing I like more than a hoodie with a skirt is a hoodie under a leather jacket with a skirt. I was admittedly a little worried that the leather jacket PLUS the leather skirt would look and feel a bit suffocating, but the sweatshirt keeps it playful enough that it works (I think…?). With the sneakers swapped out for mules, I’d even wear this out to brunch or dinner around town.

7. With A Mod(est)ified Cami

A shop-your-closet, minimalist wardrobe inspo with a black faux leather pencil skirt. Styling it up for everyday, date night, business casj & more — 1 midi skirt, 8 outfit ideas.

Pencil Skirt (similar) // Tee (TTS) // Cami (TTS) // Black Booties (TTS)

I’m going to admit something here that might surprise you: this is the first time I’ve put a cami over a t-shirt. Ever. Ok, definitely not ever. That was a thing in the ’90s, and I for sure took part in it (I even put a few tube tops over tank tops — I think I have Fergie to thank for that one), but despite the fact that this is one of the most popular looks among many of my TME colleagues, I had yet to do it as an adult. And guess what? I kinda like it. It’s an easy way to mod(est)ify a lingerie-inspired cami (legitimately excited about that part, because I’ll get waaaay more wear out of them this way). Bonus points for feeling like I’m 14 again.

8. Cozied Up With All The Warm Stuff

A shop-your-closet, minimalist wardrobe inspo with a black faux leather pencil skirt. Styling it up for everyday, date night, business casj & more — 1 midi skirt, 8 outfit ideas.

Pencil Skirt (similar) // Turtleneck (TTS) // Tan Booties (TTS) // Faux Fur (similar shape in a teddy bear style)

This one is for all you folks living out a real-deal winter, and I am as smitten as it gets. I added sheer tights (another admission: this is one of two pairs of tights that I own) and a turtleneck and topped it with my gigantic faux fur coat and it’s borderline ridiculous and I am GUH-ROOVING on it, friends. The faux fur could just as easily be swapped out for a fave puffer, though if you’ve got something in the fur genre, why. the heck. not.

Shop Black Faux Leather Pencil Skirts

Shop Black Midi Skirt Outfit ideas

Pretty excited that I’m feeling way more inspired to pull this skirt out for all sorts of year-round occasions. How are you guys feeling about leather (or faux leather, as it were) skirts, guys? Any fave looks from the above? Would love to hear how you’d style it up, too!

Cheers,
Em

Guys! Follow me on Instagram for more peeks into our life on the Northern California coast. And if you feel so inclined, pop over to my personal food + lifestyle blog, The Pig & Quill, where I share salty scribblings from my kitchen and home life. Byeeeeee!