I recently took a much-needed vacation that included hours of driving up the coast of California to visit my family, where they’ve just settled in Sausalito (hi, Mom!). And when people say that the Bay Area is the same (fairly chilly) temperature year-round, they are not joking. From a packing standpoint, I somehow managed to squeeze 10 days’ worth of clothes into the tiniest of carry-on bags. Sadly, however, I not only neglected to pack enough long pants, but also foolishly left behind my favorite leather jacket.
But the body part that wound up the coldest during my trip? My toes! Apart from my sneakers, I packed a pair of slip-on sandals that I wore basically every day—but wasn’t exactly ideal for the mid-60s temperatures. So I committed the ultimate fashion crime (for us non-Olsens, at least), and shamelessly sported funky socks with my slides for the majority of my trip. It was an adventure in itself, of sorts. What kind of socks would work with each of the outfits I packed? On a scale of 1 to crazy, just how insane would I look? Overall, things went well, and paved the way for what will perhaps be one of my transitional fashion endeavors for the fall—daily socks and sandals. Feeling inspired? Click through the above slideshow to shop some of the funkiest fall socks to start wearing now!