I just answered a question about going-out clothes during the cold months and wanted to add something that I completely forgot about…
SWEATPANTS BARCRAWL. I use the term barcrawl loosely. Basically one time my friends were all being boring on a Friday night because it was “too cold” so I suggested a sweatpants barcrawl and we just went to the bars in yoga pants, sweatshirts, scarves and uggs. But because there were so many of us it looked like it was intentionally planned.
Voila— I just solved all the worlds problems.
Honestly this is one of life’s greatest struggles. A mix of painful cold and paralyzing fomo. I feel you.
In the fall I pretty much always wear dark skinny jeans, black booties, a cute tank or blouse under a leather jacket or an oversized slouchy sweater. My school bar scene was pretty casual so no one really went over the top, but I always dressed up a simple tank or sweater with a statement necklace or earrings. Jcrew is my go-to for necklaces, and forever 21 and H&M have a lot of fun, oversized earrings— studs though, I always stick to studs.
In the winter, anything goes. I seriously wore a knee length parka to a bar once in negative five weather. The dedication is real. Anyways, I swap out the fall booties for full on knee high black leather boots (all my boots are from Nordstrom, I have found they have the best collection of classy boots that are good quality) and wear chunkier knits / more layers.
My best piece of advice for going out clothes is — better to be too classy than too tacky. Crop tops and short shorts are fun for summer, but I avoid tight skirts or high heels like the plague.