Okay, so I had this itch the other day, you know? I was thinking about some old-school styles and the whole “black dress over a white shirt” thing from the 90s just popped into my head. I remember seeing it everywhere back then, and I thought, why not try and recreate that vibe myself? It’s been a while!

The Hunt for the Right Pieces
First things first, I had to actually find the components. This is always the most fun part for me, like a little treasure hunt in my own closet. I started by looking for a suitable white shirt. I knew I didn’t want anything too stiff or too fitted. I was aiming for that slightly relaxed, almost borrowed-from-your-boyfriend look, but not overly huge. I sifted through a few options. One was too sheer, another too formal with French cuffs – nope. Then, aha! I found this one, a pretty basic cotton button-down, a little soft from wear, which I figured would be perfect. The collar wasn’t too pointy, not too wide. Goldilocks, you know?
Next up: the black dress. This was key. I remembered having a simple black slip-style dress. It’s one of those thin strap, kind of A-line things, nothing too fancy. I dug it out. It’s made of a slightly slinky material, which I thought would create a nice texture contrast with the cotton shirt. I checked the length – it hit just above my knees. Perfect. I didn’t want a maxi dress for this particular look; it had to have that slightly edgier, youthful feel of the 90s.
Putting It All Together – The Experiment
Alright, moment of truth. I put on the white shirt first. I decided to leave the top two buttons undone for a more casual, less “office” vibe. Then, I carefully slipped the black dress over the top. This part always requires a bit of fiddling, doesn’t it? I had to make sure the shirt collar was sitting nicely, peeking out from under the dress straps. I also played around with the sleeves of the white shirt. I rolled them up a couple of times, just to show a bit of wrist and make it look more intentional and less like I just threw things on, even though that’s kind of the vibe too!
I then spent a few minutes adjusting how the shirt lay under the dress. Did I want it perfectly smooth, or a bit rumpled? I opted for slightly rumpled. It felt more authentic to that grunge-lite aesthetic. I also made sure the dress wasn’t bunching up weirdly over the shirt.
Thinking About the Finishing Touches
Now, for the accessories, because that’s what really sells a 90s look, right? My mind immediately went to footwear.

- I thought about some classic trainers, but it didn’t feel quite right for what I was going for.
- Then I remembered my chunky black boots. Bingo! They have that slightly stompy feel that was so popular. I pulled those on.
- I briefly considered tights, maybe some sheer black ones or even fishnets if I was feeling bold, but I decided to keep it simple with bare legs, since the boots gave enough of a statement.
For jewelry, I kept it minimal. Maybe a thin silver chain or a simple choker would have worked, but I actually decided to go without a necklace this time, letting the collared shirt and dress neckline do their thing. Sometimes less is more, even with a throwback look.
The Verdict
So, I stood in front of the mirror and took a good look. And you know what? I was pretty happy with it! It definitely gave off that 90s nostalgia I was aiming for. It felt comfortable, a bit edgy, but still totally wearable. It’s funny how these styles come back around. It’s a simple combination, but it has a certain attitude. I felt pretty cool, actually. It was a fun little style experiment for the day, and definitely something I’d do again when I’m feeling that retro vibe. Success, I’d say!