Three Ways to Wear a Black Midi Skirt

I shied away from the “midi” length for a while. I thought it was super awkward and extremely hard to find shoes that actually worked. As time went on, I warmed up to the midi. What’s not to love? It doesn’t ride up as easily as above the knee styles, less risk if the wind blows, always looks sleek and you only have to shave below the knee. Three times a win!

I was doing a Boohoo.com haul – looking for some affordable dresses for a “non-wedding day photo shoot” (#covidbride), and I saw this pleated, flowy number that I had to try. Plus, it was $16, so basically it bought itself. This one is sold out now, but here are some similar ones – all under $50. FYI – we will get into steals and deals later on.

It arrived and I LOVED it. It was a little longer than I expected, but there was still plenty that could be done with it. I immediately knew it would be a summer (and fall and spring and winter) staple. The length and shape can go from day to night, casual to office, trendy to timeless. I’m already picturing the re-do of this post when we get back to sweater and boot season – OMG YAY – so cute in my head! 

For now, I’ve determined three of my fav ways of how to style this black pleated maxi: out and about, soiree chic and to the office. Most of what I’m wearing has been in my closet for years, so I’ve linked to similar items – all under $25 each.

Black Midi Skirt Options: here, here and here

Out and About

Probably my favorite of all three looks, just because I can see myself wearing it the most. I tied up a graphic tee that my friend Maria bought me at a concert of my favorite band Dashboard Confessional (I had a very long emo phase). Mine is a ladies’ cut, so it is a slim fit. However, I think if you didn’t have a ladies’-specific tee, the boxiness would still look super cute with this since the fullness of the skirt would balance the top out. Don’t want to tie it up? Just tuck it in! 

I paired this with my trusty slip-on black sneakers (They are slim and low-profile so they don’t creep up and cut of the line of my short little legs too much and perfect for when I am running out the door) and a multi-colored clutch to tie in the color from the graphic tee and even more pop to keep it bright and casual. 

I was undecided on the necklace and could still go either way. If you want a more sporty spice look, get rid of it. If you like making it more feminine, keep it!

Graphic Tee: here,here,here
Slip-on shoes: here and here 
Multi-color clutch: here and here
Accent necklace: here and here

Social Soiree

I was originally going to call this look “Garden Party”, but I don’t know a single person who has actually been to one of those. So here we are…”social soiree”. I love a monochromatic look. It feel like it elevates separates to be a true cohesive outfit. Black on black? Even better. I got this bodysuit for $6.99 (WHAT?!) during the same Boohoo.com haul when I got the skirt. It’s sold out now, but I’ve linked some other options below. Any type of black bodysuit and fitted top would do here. 

I also love how tall a monochromatic look can make you appear because you’re not breaking up the line of sight from your shoulders to the bottom of the skirt. It’s a great tip for those of us on the petite side or dangerously close. However, we still want to accessorize in a way that gets us noticed, don’t we? I went with a hot pink clutch that is just big enough to hold my phone, cards, key and lipstick and called it a day. This guy has a strap so you can use it as a wristlet to keep your hands free. I got it secondhand, but I think it was originally from Target. 

Let’s talk about this shoe.  The watercolor floral is so soft and versatile. Realistically, I could have accessorized with: yellow, green, blue or white instead of the pink I chose to highlight. That’s the beauty of multi-colored accessories. They provide so much more versatility than a solid and are fun as heck. I got these at a Payless Shoes Going Out of Business Sale, but floral shoes are always going to be in style. I’ve linked a few below. I think the key on finding the right pattern is one that isn’t overly “crisp”, otherwise you run the risk of tablecloth territory. 

Bodysuit: here, here and here
Shoes: here, here, here and here
Clutch: here, here and here

To The Office

As companies continue to adopt less rigid wardrobe guidelines, it has allowed women to take risks in silhouettes that can look feminine, but also fully in-charge. Since this midi skirt is so flowy and unstructured, I wanted to use a traditional top half to keep it professional. 

I love a bright blazer. When I was in “Corporate America” I had one in nearly every color. The structure showed polish and organization, the color expressed personality. I paired this red one (from H&M back in the day) with a black and white silk, patterned blouse. I tucked my top into my undies so that it stayed as streamlined as possible. You don’t want it to balloon out of your waistband. A blazer can already add bulk to you, so this is an important step. You could use a bodysuit or a fitted top here just the same in order to fix this problem. 

I liked that the pattern was angular, again, which feels more professional than something floral or swirly. Lots of unspoken messages in this outfit. Once closing time hits, you can shed the blazer and head to whatever is the next item on your agenda! 

I thought it was important that I paired this “inspo” outfit with a bag I would have actually used on a busy work day. This one in particular has great details – suede end panels and fringe that would definitely draw some attention. It was a free Victoria’s Secret giveaway if you purchased a mountain of pink-colored items back in the day. I just flip the logo toward the inside to keep it “profesh”. If you work in a more traditional office setting, maybe a tote with more structure and less flair would suit you better.

I am not linking to plain black pumps, because there is nothing special about these and likely every woman already has a pair in her closet. If not, invest in a pair. I like to have a round toe and a pointy toe in my closet at all times. You can almost never go wrong with a black pump. This is my PSA. Thank you. 

Blazer: here and here
Top: here and here
Tote: here and here

So there you have it. I hope it didn’t take you nearly as much convincing as it took me to finally click “add to cart” on a Black Midi Skirt. It’s a staple that will allow you to reuse time and time again, and likely look different on each occasion.

Don’t want to read this article? Check out the video version on my YouTube channel instead!