I decided to test my “stalkerazzi” skills this past weekend at San Francisco’s Westfield Shopping Centre and in random places around the city.
I tried to find some stylish looks within the hustle and bustle. I was looking for someone that stood out from the crowd - in a good way. Don’t get me wrong, while walking through the various neighborhoods of SF, there are many trendy people - but it’s seldom that I find someone that stands out with a unique style. I’m looking for someone who doesn’t look avant-garde, experimental or looks like they just stepped out of an Urban Outfitters catalog.
Perhaps I took pictures in the wrong area - I was in the tourist-heavy neighborhood of Union Square. Many people started looking alike after a while - and when I did see someone who had genuine style, they were walking too fast for me to snap a photo of them. They must’ve knew that I was “stalkerazzi-ing” them.
Nonetheless, here’s what I found and some stories (at least in my eyes) behind the outfit:

What’s her story? She is calling her “shopping lifeline” to justify her recent purchase. She’s not 100% comfortable with the purchase of a shirtdress and a boldly colored belt. Her friend is telling her to return the belt, but she’s thinking differently.
What works for her: I am loving the Kimono-inspired top and the springy tone of the the outfit. The light blue skirt and matches well with the white without making it too brighty.
What doesn’t work: The flats. I am not big on them to begin with.
What’s his story? His blind date is shopping inside H&M and he’s talking to his homeboy to tell him how much of a bust the date is. His epidimec of wearing sunglasses indoors has clearly spread to the other girl walking out of the store.
What works for him: You can’t really see it, but he was carrying a bag from the Cheesecake Factory. I wonder what he ordered.
What doesn’t work: One of my biggest fashion qualms is wearing sunglasses indoors. I know the SF Shopping Centre is highly illuminated, but I just think it is very unnecessary to wear sunglasses indoors. Unless you just got your eyes dialated, blind, a heavy user of narcotics or you are suffering from an intense hangover - don’t do it.
What’s her story? A lady who has a quirky style. She likes classic garments like the trench, but she always likes to add a twist of color to all that she wears. She’s works as a nurse, but on the side, she is a very talented artist who’s eye for color that will rub off on her child.
What works: The trench. I absolutely love the pattern and the spring-friendly shade. The knee high socks add a good touch because if they weren’t there, it would look like she wasn’t wearing anything underneath - that would just be in bad taste. And how cute is that kid?
What doesn’t work: Honestly, I couldn’t find anything terrible in what she was wearing.
What’s her story? A photographer who was looking for subjects to add to her portfolio for an exhibit she’s working on. Frustrated, her and her friend are exiting the mall annoyed with the lack inspiration.
What works: The hat was the thing that caught my eye as I took her picture from the second floor.
What doesn’t work: She was too far for me to analyze her outfit.
What’s her story? Her and her fiance are at Crate and Barrel registering for gifts. They are a classy couple with a modern eye for home decor. She is a owner of a start-up online high-end fashion boutique and he is a savvy IT in Silicon Valley. Her artistry and his need for structure make a perfect match.
What works: The coat was a fabulous purple. The back detailing was the kicker. If you saw the outfit from the front she had a romantic ruffled lavendar blouse. Paired with some brown boots and a huge hobo bag, her whole look worked.
What doesn’t work: She was moving around too much for me to get a good picture of her.
What’s his story? He’s a college kid majoring in graphic design who is obsessed with Superman. He’s currently working on his own graphic novel about a superhero based on him.
What works: I like how he’s still a child at heart with the novelty Superman t-shirt.
What doesn’t work: What’s with the draping of the sweater across the shoulders? We’re not in the Hamptons.
What’s their story? You know that movie Mean Girls? The movie was based on these girls.
What works: They are all walking in sync. How cute.
What doesn’t work: Uggs. Need I say more? Yes I do. I see a fashion oxymoron in how two of the girls are wearing the furry boots and one of the girls is wearing flip flops.