So, I’d been looking at these tall brown boots in my closet for a while. You know how it is, you buy something, you wear it a bit, then it just sits there. I decided it was time to actually get some serious wear out of them. I mean, they’re good boots.
Figuring out the Basics
My first thought, as always, was jeans. That’s just my go-to. I grabbed a few pairs. The skinny jeans were the obvious choice for tucking in. I tried a light wash, but honestly, the dark wash denim looked much better with the rich brown of the boots. It just felt more put-together, less… I don’t know, messy?
For tops with the jeans, I kept it pretty simple. I pulled out a cream-colored cable knit sweater. That worked. Looked classic, felt comfortable. Then I tried a simple black turtleneck. Also good. It let the boots be the main focus, which was kind of the point.
Moving on to Skirts and Dresses
Okay, jeans were sorted. But I wanted more options. So, I moved on to skirts. This is where it got a bit more experimental for me. I had this A-line corduroy skirt, sort of a rust color, hit just above the knee. I put that on with the boots, added some opaque tights because it’s not exactly summer, and you know what? It actually looked really decent. The texture of the corduroy with the leather of the boots was nice.
Then I thought about dresses. I have a few sweater dresses. I picked out a charcoal grey one, fairly simple, not too clingy. Pulled the boots on. That was a winner. Super easy outfit, looked good, and was incredibly comfy. I also tried a slightly more flowy, floral midi dress. I wasn’t sure about this one, thought it might be too much, but with the boots, it kind of grounded the dress, made it feel more casual and wearable for daytime.
What I Learned Works
So after all that trying things on in front of the mirror, here’s what I figured out for myself:

- Skinny Jeans: Definitely the easiest win. Dark wash is my preference with brown boots.
- Sweaters: Can’t go wrong. Cream, oatmeal, black, grey – all good. Simple is often best.
- Skirts (Knee-length or Midi): A-line or slightly straighter cuts seemed to work well. Corduroy, denim, even some thicker knit skirts. Tights are essential if it’s cold.
- Sweater Dresses: Yes. Absolutely. So easy and looks great.
- Colors with Brown: I found that creams, olives, deep reds or burgundies, mustard yellow, and of course, different shades of blue denim, all looked good with the brown. I wasn’t a huge fan of pairing them with very bright, almost neon colors, but that’s just me.
The key for me was making sure the proportions felt right. With tall boots, you don’t want your top half to be too overwhelming or your skirt to be an awkward length that visually cuts you off.
Honestly, it just took a bit of time pulling stuff out of the closet and actually putting it on. Sometimes you just have to see it on your own body. These boots are definitely more versatile than I initially gave them credit for. Now I’ve got a few solid outfit formulas I can rely on. So, if you’ve got a pair of tall brown boots gathering dust, I’d say just start experimenting. You’ll find what works for you.