Alright, so I decided to tackle the leather pants today. They’ve been hanging in my closet for a while, kinda intimidating me if I’m being honest.

Getting Started
First things first, I pulled them out. They’re faux leather, not the real deal, but they have that sleek look. I actually tried them on to make sure they still fit comfortably. Check. Felt okay.
Now, the big question: what goes on top? This is where I usually get stuck.
The Top Half Struggle
I initially grabbed a basic white t-shirt. Put it on. Stared in the mirror. It was… fine. Just fine. A bit boring, maybe? Felt like it needed something more.
Okay, plan B. I thought about a silky blouse. Found a black one. Tried that. Hmm, looked a bit too ‘going out’ for just a regular day. Not the vibe I wanted.
Then I spotted my favorite cozy, slightly oversized grey sweater. It’s soft, comfortable, definitely not flashy. Pulled that on over my head. Okay, this felt better. The softness of the sweater seemed to balance out the toughness of the pants. Yeah, I liked this contrast.

Shoes and Outerwear
Next up, shoes. What works with leather pants and a comfy sweater?
- Sneakers? Tried my white ones. Looked okay, very casual.
- Heeled boots? Nah, not feeling heels today.
- Flat ankle boots? Found my black chelsea boots. Slipped them on. Yes. This felt right. Grounded the outfit, kept it practical but still looked put-together.
It’s a bit chilly out, so I needed a jacket. My first thought was a black blazer. Put it on. Looked a bit too… office-y? Took it off.
Then I reached for my trusty denim jacket. A classic blue wash. Threw it over the sweater. Stood back. Okay, I liked this! The denim added another texture, made it feel more relaxed and layered.
Final Check
So, the final combo was: faux leather pants, cozy grey sweater, blue denim jacket, black chelsea boots. I didn’t bother with much jewelry, just my usual watch. Grabbed my simple black crossbody bag.
Looked in the mirror one last time. Felt good. Comfortable enough to walk around in, looked intentional but not like I spent hours planning it (even though I kinda did, haha). Success! Ready to head out.

So that’s my little process for figuring out the leather pants today. It’s mostly trial and error, seeing what feels right, you know?