Way back in the day–around my college years–I would occasionally wear over-the-knee socks or boots with a short dress because I loved that era of the Fresh Prince where Ashley would style looks with thigh high socks. While I don’t see myself pairing a fitted dress with boots nowadays, I did opt for an oversized sweater dress to keep the look updated. This option, known as “lampshading” in the fashion world, provides a better balance to the look. Thinking back to when I would wear a tight dress with over-the-knee socks instead of something with a looser fit makes me cringe. Fitted can quickly veer into the wrong direction, whereas the oversized style keeps it casual enough for the daytime.
“Showing skin in the winter? Wouldn’t your legs get cold?”
To answer that question simply, no if it’s done correctly. This may not work for colder states, but Texas has bearable winters so I was pleasantly surprised with how warm this outfit feels. The dress is essentially an oversized sweatshirt (with pockets!!) so the inner lining kept my body warm, while the combination of high boots and knit socks kept my legs warm. The trick to wearing this type of outfit and staying weather appropriate is picking the right fabric. Of course, you can always add opaque tights if you aren’t comfortable showing a peek of skin.