Honestly, trying to pull off shorts with thigh boots felt kinda silly at first. Like, where do you even start? But hey, I see people do it online, figured why not give it a go myself. You know me, gotta try everything once.
The First Attempt: Total Mess
Grabbed my oldest pair of denim shorts – the comfy ones, kinda faded. Threw on my black suede thigh boots, the ones with a small heel. Stood in front of the mirror… and cringed hard. Legs? They looked weirdly chopped off. The shorts felt too casual, the boots too much. It just screamed “wrong”. Like, really wrong. Almost took a pic for laughs, but nah. Deleted it fast.
Trying to Fix It (And Kinda Failing)
Thought maybe different boots? Dug out my cheaper faux-leather flat ones. Nope. Legs still seemed short and awkward. Tried longer shorts. Worse. Just looked frumpy. Got frustrated. Almost tossed the whole idea. Was ready to just wear them over jeans again, safe and boring.
The “Oh, Maybe?” Moment
Okay, so maybe it’s about balance. Needed something to make it look intentional, not accidental. Swapped the faded shorts for a more structured pair – dark wash, straight leg cut, hit mid-thigh. Then, remembered this basic black oversized sweatshirt I always forget about. Pulled that on. Added some simple silver hoops. Back to the suede boots.
Looked in the mirror. Huh. Didn’t hate it this time. The dark shorts matched the boot better, the sweatshirt hid my hips a bit and made it feel less… leggy? Put on my big black tote bag. Kinda liked this messy, edgy feel. Took a mirror selfie. Looked put-together-ish. At least better than the first disaster!
What Actually Ended Up Working
Played around with that outfit for a while. Found a few things that really clicked:
- Dark Wash Denim Wins: Doesn’t matter if they’re jean shorts or something like tailored black shorts, dark colors blend better with the boots.
- Big Tops Are Key: Cropped tees? Disaster on me. Oversized tees, sweatshirts, chunky knits – that works way better. Creates shape on top so legs + boots aren’t the only thing.
- Boot Height Matters: My flats never looked quite right. Needed that little heel to feel… cooler? More balanced? The heel just helped.
- Keep the Accessories Simple: Too much jewelry felt cheap. A good bag and maybe a hat worked better.
Would I wear this every day? Probably not. It’s definitely a “going out” or “trying to look cool at the mall” vibe for me. Takes more effort than throwing leggings under them. But now? I kinda feel like I cracked the code, at least for my own weird body type. Won’t lie, I wore the sweatshirt-shorts-thigh boots combo to get coffee yesterday. Felt pretty damn good.
