Alyssa’s everyday Zara Boots ($40)

Although I tried to fight it for many years, when winter rolls around in San Diego, it’s time to put the flip flops and sandals away. This is the time of the year when San Diegans are able to show off their boot game, so I went hunting in North Park on my way to happy hour for the best ones. I parked on the neighborhood streets a few blocks down and began making my way to Working Class, a local eatery with great happy hour snacks and beer. On the short stroll, I came across Alyssa, a yoga teacher from Del Mar, who was headed back home from Pigment.

Her black Chelsea boots (Zara, $40), were the perfect compliment to any outfit, and could be dressed up or down. Alyssa decided to rock them with a graphic t shirt and light washed denim frayed at the bottom. “I wanted to get Doc Marten Chelsea boots but they were way too expensive ($150), so I settled for these from Zara. They’re really comfy!”

Resilient, decade old moccasin booties ($50)

After the happy hour with friends, we decided to head over to Seven Grand to enjoy the ambiance and whiskey. It was then that Mac’s moccasin booties glided past me, and I stopped to inquire where she snagged them from. Mac, an environmental consultant, had picked them up from Shiekh Shoes ($50) at the Valley Fair Mall in the Bay Area, where she’s originally from.

“I’ve had these shoes for over a decade now, as you can probably tell. I like to buy pieces that I know I’ll keep with me for years.” I commented on the glitter splattered around the booties, to which she laughed, “I somehow get glitter on everything. I can’t even tell you what it’s from. I’m always randomly crafting.”

Unique dark purple Docs ($150)

The final boots to end my hunt were ones that I don’t see often - dark purple Doc Martens ($150, Old School Shoes in Santa Cruz) on the feet of Sofia, a painter from Seattle. “I’ve always wanted Doc Martens but I wanted them to be different than all the black ones everyone gets. I chose purple because it’s my favorite color, and I feel like it makes more of a statement and helps your outfit pop a little more.”