Okay, so everyone’s been asking about my skirt outfits lately. Not really, but I decided to actually document the struggle for once. Because let’s be honest, sometimes getting dressed feels like a full-time job, especially with certain items.

That One Skirt
So, I had this skirt. You know the type. Bought it on a whim, looked great on the hanger, or maybe the ridiculously skinny mannequin. Mine was this pleated midi, a nice enough navy blue, but the fabric? A bit… particular. It creased if you looked at it wrong and had this weird sheen that could either look expensive or cheap, depending on the light and, I swear, the phase of the moon.
I decided, this weekend, I am wearing this skirt. No more excuses. It was practically gathering dust, judging me from the closet.
The Great Top Debacle
First, I grabbed my go-to: a simple white t-shirt. Tucked it in. Looked okay. Just… okay. Like I hadn’t really tried. And with this skirt, ‘okay’ wasn’t going to cut it after all the closet guilt.
Next up, a silk camisole. Felt a bit too much like I was heading to a fancy dinner when I was actually just planning to get groceries and maybe, just maybe, meet a friend for coffee. So, no. That went back on the hanger pretty quick.
Then I thought, what about a sweater? I pulled out a few:

- A chunky knit. Made me look like a walking marshmallow. The skirt just got lost.
- A fine-gauge merino wool. Better, but the neckline was wrong. Too crew-necky.
- A slightly oversized cashmere v-neck. Now we were getting somewhere! But the color… a bit too close to the skirt, looked like a failed attempt at a monochrome outfit.
I must have tried on at least seven or eight tops. My bedroom floor started to look like a clothing store exploded. You know that point where you’re sweating, slightly annoyed, and considering just wearing pajamas out? Yeah, I was there.
Footwear Frustrations
And don’t even get me started on shoes. Shoes can make or break an outfit, right? Well, they were definitely trying to break this one.
Ankle boots? Made my legs look shorter with the midi length. Not the vibe.
Sneakers? Too casual for the slightly dressier feel I was accidentally creating with the better top contenders.
Ballet flats? Felt a bit… juvenile with this particular skirt’s style.

Heels? Please, I was going for coffee, not a red carpet.
I eventually settled on some low block-heeled loafers. They felt like a compromise. Not thrilling, but they didn’t actively sabotage the skirt, which at this point was a win.
The “Final” Look and Some Thoughts
So, after what felt like an eternity, I landed on the skirt, a cream-colored, slightly looser knit sweater (found it hiding in the back of a drawer, of course), and the loafers. Added a simple long necklace to break up the sweater. Did I feel like a fashion icon? Nope. Did I feel presentable enough to leave the house and not embarrass the skirt? Yes, finally.
The whole process was a reminder. Sometimes those ‘easy’ pieces are the hardest to style. You buy something thinking it’ll be versatile, and then it demands a whole new supporting cast of clothes you don’t own or that don’t quite work.

It’s a whole thing. You start with one item, like this skirt. And suddenly, you’re questioning your entire wardrobe, your life choices, why you even bother with clothes. It’s exhausting! But hey, at least the skirt got an outing. It’ll probably go back to judging me from the closet for another few months, but we did it. We survived the outfit skirt day.