Okay, let’s get into this. It feels like ages ago I even started trying to make dresses and booties work. For the longest time, I just thought, nope, not for me. Looked clunky on everyone I saw, honestly. But then, you see it done right, and you’re like, wait a minute.
My First Awkward Attempts
So, I dived in. Grabbed a few dresses, hauled out all my booties. My bedroom looked like a discount shoe store exploded. First up, I tried a cute, kinda short, flippy skirt dress. Paired it with some flat, chunky ankle boots. Disaster. My legs looked like they’d been chopped off. Seriously, it was bad. I remember thinking, “This is why people stick to sandals or heels with dresses.”
Then I thought, okay, maybe a longer dress? So, I pulled out a midi dress, one of those flowy ones. Tried it with the same chunky booties. Still… not quite. It was better, but something was off. The proportions felt weird. It was like my feet were having a separate, very heavy party from the rest of my outfit.
Figuring Out the Annoying Details
I started noticing things. The height of the bootie shaft was a big deal. Too high, and it cut off my leg at a weird spot, especially with midi dresses. Too low, and sometimes it just didn’t look substantial enough, if that makes sense. And the heel! Oh boy, the heel makes a difference. Flat booties were the trickiest for me with dresses. They just… dragged everything down.
I spent a good few weekends just trying combos. I’d put something on, stare in the mirror, take a photo, and then immediately change. My family thought I was losing it. “Are you okay in there?” my husband would yell through the door. “Just battling fashion!” I’d yell back.
One particular nightmare was trying to wear booties with a more fitted, knee-length dress for a work-ish event. I had these sleek, black heeled booties I loved. But with that dress? It was a no-go. It made the whole look feel… confused. Like, am I trying to be serious or am I trying to be trendy? Couldn’t decide, and it showed.
The “Aha!” Moment (Sort Of)
The real shift happened when I was getting ready for my friend Sarah’s art gallery opening. It was one of those cool, slightly edgy events, and I really wanted to wear this new dark floral maxi dress I’d bought. But it was autumn, a bit chilly, and heels felt too formal, sneakers too casual. Booties were the only answer. I must have tried on every pair I owned. It was getting ridiculous. I was sweating, makeup half-done, dress on and off about ten times.
Then, I grabbed a pair of slightly more fitted ankle booties, with a bit of a pointed toe and a decent block heel – not too chunky, not a stiletto. And I put them on with the maxi dress. And I actually didn’t hate it. The dress had a slit, so you’d get a peek of the bootie. The pointed toe helped, I think. It didn’t look so… abrupt.
That was the moment I realized it wasn’t about a dress and a bootie. It was about which dress and which bootie. Groundbreaking, I know, but it took me ages of looking frumpy to get there.
What I’ve Settled On (For Now)
So, after all that trial and, mostly, error, here’s what I’ve kinda landed on. This isn’t fashion gospel, just what works for me and my legs.
- Flowy Midi/Maxi Dresses: These are my go-to with heeled ankle booties. Especially if the bootie has a slimmer ankle or a bit of a V-cut at the front. It stops that “tree trunk leg” look.
- Shorter Dresses (Above the Knee): This is still tricky. If I do it, the booties need to be sleek, probably heeled, and I usually go for ones that don’t come up too high on the ankle. Sometimes, adding black tights can bridge the gap if I’m wearing black booties, makes it look more intentional.
- Knit Dresses: Sweater dresses in the fall? Yes, please. These actually work pretty well with a variety of heeled booties, from sock booties to slightly chunkier ones. The texture seems to help.
- Bootie Color Matters: Nude-to-me booties, or booties that match my tights, can really help elongate the leg. Black on black is easy. But a starkly contrasting bootie with a bare leg and a dress can be a tough one to pull off unless you’ve got legs for days.
Honestly, it’s still a bit of an experiment every time I try a new dress-bootie combo. Some days I nail it, other days I look in the mirror and think, “Well, that was a choice.” But I’m not scared of it anymore. I just know I need a bit more time in front of the mirror if booties and dresses are on the agenda.
