Alright, so I’ve got these black riding boots, and honestly, they were collecting a bit of dust. I figured it was time to actually, you know, wear them. But then the whole “what do I wear WITH them?” thing hit me. It’s not always as straightforward as you’d think, or at least it wasn’t for me this time around.
My First Go-To: Jeans, Obviously
So, the first thing I did was grab my trusty skinny jeans. Seemed like a no-brainer. I pulled them on, tucked them into the boots. Yeah, that worked. Pretty standard, right? I tried a few different tops. A basic long-sleeve tee was fine for super casual. Then I threw on a chunky knit sweater, one of those oversized ones. That felt much better. More balanced, I guess. I also tried a more fitted turtleneck with a blazer over it. That looked pretty smart, actually. So, skinny jeans were a definite yes, but the top half needed some thought.
Then Came the Leggings Phase
Next up, leggings. Because, comfort. And they slide into boots like a dream. I have a bunch of plain black ones. First, I tried a shorter top and, nope, not for me. Just felt a bit… unfinished with the riding boots. So, I switched to a longer tunic-style sweater. Big improvement. It covered what needed covering and just looked more put-together. I also tried a long, open cardigan over a simple top with the leggings and boots. That was a winner. It felt cozy and looked decent enough to go out in.
Venturing into Skirts and Dresses (This Was Tricky)
This is where things got a bit more experimental for me. I don’t wear skirts with tall boots all that often.
I pulled out a few:
- A shorter, A-line skirt. With tights, it was okay. But it felt a little… young? Or maybe just not my vibe right now with these particular boots.
- Then I tried a knee-length pencil skirt. Hmm. The proportions felt a bit off with the riding boots. Maybe it’s just me.
- Sweater dresses! Okay, this was a good one. I have a couple that hit just above the knee. Threw one on with the boots, and it was instant. Easy, comfy, looked pretty good. Didn’t even need to think too hard about it.
- I also tried a slightly more flowy, midi dress, just to see. It kind of worked, but I had to make sure the dress didn’t clash with the structure of the boots. A darker floral print was better than something too summery.
What I Learned Through All This Trying-On
So after all that rummaging through my closet and trying things on in front of the mirror, a few things became pretty clear. For me, anyway.
Slim silhouettes on the bottom are key with riding boots. Skinny jeans, leggings, or even slim-fit trousers just tuck in neatly and don’t fight with the boot. Baggy pants over them? Not a look I was going for.
Tops that have a bit of length or volume seem to balance out the tall boots. Tunics, longer sweaters, or even a blazer helped. With dresses, something that flows or has a bit of weight, like a sweater dress, just felt right.
It wasn’t about buying a whole new wardrobe. It was about actually spending the time to see what I already had could work. Sometimes you just gotta make a bit of a mess in your room and try stuff on. No magic formula, just seeing what feels good and looks decent enough to walk out the door in. And now, I’ve got a few go-to combos, so those boots won’t be gathering dust anymore. Job done, I reckon.
