SPG: What to wear in San Francisco

“The coldest winter I ever saw was the summer I spent in San Francisco”  — Mark Twain

In the past when I’ve thought of San Francisco, I would always think of the tech industry  and the now iconic style of a hoodie with a tee, jeans, and sneakers that goes with it. An hour in SF is enough to put this stereotype to shame – there is so much more fashion and style happening in San Francisco than I previously realized. For starters, there are quite a few fashion companies headquartered in San Francisco: Levi’s, Gap Inc, Cuyana, and Brooks Brothers just to name a few. The techies want in on the game and so San Francisco is leading the emerging fashion + tech industry that has started making big waves. Companies like Stitch Fix, ThreadUp, TheRealReal, and Poshmark are changing and reshaping e-commerce and online consignment.

On the street style level, there are some seriously well dressed women trotting around Grant Avenue. After all, half of the world’s billionaires live in the Bay Area (74 if you’re curious) – it now make total sense why Goyard opened it’s first US store in San Francisco, right? But wealthy, well-dressed (mostly over-styled, (am I right?)) women can be found all over the world.

What makes the San Fran street style stand out is it’s connection to it’s history and, now, it’s connection to the tech industry. While the techies are rapidly trying to change the landscape of SF and pricing everyone out in the process, the city remains resolutely proud in its *sometimes* grungy, fog covered neighborhoods that are fighting desperately to keep their identities. The Haight will always be the unkempt home of hippies and the Castro will remain the beating heart of the LGBTQ community. Don’t mess with the Mexican food of the Mission District and don’t even think about trying to clean up the Tenderloin. The battle for SF that is currently being waged by the techies has, in my opinion, brought out the pride of it’s long-time residents in spades. And there is something liberating in that pride. SF is now a place where it’s residents don’t feel afraid to express themselves and this is bleeding into the street style.

The women and men of San Francisco are wearing some of the most creative outfits I’ve come across and it makes me damn jealous (sometimes) that I left the house in a white tee shirt and jeans. It makes total sense that there are a lot of emerging fashion lines happening in SF right now and that, at the same time, there remain some of the best resale stores in the country. The new with the old, the tech with the history, and the constant push and pull that SF seems to experience between finding out how both will survive and stay in this small city on the water.

So what does one wear in the city that is attempting to seamlessly combine fashion and technology? To get the answer, I spoke with a very on point woman, Layne Cross.


Layne Cross has one of the best individual styles I’ve come across. The first time I met Layne she was wearing an orange dress (before everyone started buying orange) with one big ruffle and some boots – it was dead cool. She always looks amazingly pulled together in a way that is truly her own. It’s no surprise really as Layne has worked in retail management for over 10 years in the San Francisco Bay area. Here are her thoughts on what to wear in a city that famously experiences four seasons in one day.

Me: How would you describe San Francisco street style?

Layne: San Francisco street style is extremely eclectic and it also depends on what part of the city you’re in. It can range from the classic country boots and leggings and a really cute flannel to super funky mom jeans, a vintage tee, and a leather jacket to even the more bohemian girl who is wearing a floral dress, cargo jacket, and booties. 

Then there’s also this mix of very high-end edgy in  the downtown area. You’ll see a lot of street style with Saint Laurent and some of the higher-end brands that kids shop at Barneys, and stuff like that. 

So it really is extremely eclectic. For all the places that I’ve travelled, it’s some of the most extensive and wide range of style that I’ve seen. 

Me: I’m always in the same place in the city so I always see the same people.

Layne: It depends on where you go. Like, you go to the Marina and you see yoga pants and country boots, or a great Nike sneaker and a puffer vest. 

You go to the Mission, you’re getting a completely… you’re getting like a very cool girl vibe. The guys have just great outfits, like super skinny jeans, nice oxford button-up all the way to the top. Like very cool. 

Then the downtown definitely has a bit more of… there’s the business side of it but there’s also street style, like fashion style. It’s definitely a bit more avant-garde and trend driven, because a lot of people, like the young people that you see that are running around downtown actually work in the industry. 

Grant Avenue is full of those amazing boutiques like Dior and the Valentino store is amazing. So there are actually those people who are in it and it’s definitely more like a lifestyle for them. It’s very thoughtful rather than like a vibe. 

Me: What are some of the key pieces that you think you need in San Francisco?

Layne: Leather jacket, leather jacket, leather jacket. Need a leather jacket, for sure. That is great for like a night out or even throwing over something like a cute boho dress. I even wear my leather jacket to and from Soul Cycle. It’s just like one of the pieces that always just elevates your look. 

Another key piece is a fashion sneaker. I just saw these awesome pair of gold Nikes. I don’t care if it’s like that or if it’s just a regular Nike or a really cool Air Jordan that’s vintage. But a fashion sneaker is a must. I just got mustard green Converse, perfect for the fall, like done. 

So those are two. Then I also think like a day-to-night dress. I’m a dress girl. I’m actually a dress and jeans girl, but like a day-to-night dress. A dress that you can wear with sneakers or booties, and then one that you can also throw on like a great heel and just go. 

A lot of it’s about effortlessness in San Francisco and like adapting to the insane weather. So the more ways you can wear something, the more use you’ll get out of it. We definitely don’t dress for seasons. We dress for what’s the weather going to be like at 10:00 a.m. and what’s it going to be like at 5:00.

Me: What are the shoes that you would pack, other than sneakers? Do you go out to dinner in sneakers?

Layne: I think it depends on how you style them. I think some places it’s okay to go out to dinner in sneakers. In the Mission district for sure. 

I definitely think like a bootie, throw on a bootie. Again, we don’t dress for seasons so like a bootie is great year round, hands down the best thing ever. And you can wear them with dresses, you can wear them with jeans, you can wear them with pretty much everything. Wear them with cut-off shorts. It just looks it’s kind of a great look. So I would go with like a bootie.

Me: A bootie and sneakers, and you’re done?

Layne: Yes. Heels are a little impossible in the city. People definitely use Uber and Lift, but you’re walking around and that’s part of enjoying the city. Heels are like a no-go, for sure. 

Me: What bag?

Layne: Crossbody.

Me: Big or small?

Layne: I would say a convertible crossbody. Something that you can use as a clutch and then also throw it across if you’re going out to dinner. That sort of thing. Something to just slightly elevate your outfit. 

I also do like a pop of color because we wear a lot of black and a lot of neutrals in San Francisco. So if you can add like a pop of color, I’m thinking like a red patent or even a great kelly green or forest green. Something like that right now that’s a great way to go. It adds also a little interest to your outfit. 

But yeah, crossbody for sure. Convertible crossbody. 


Shop the story:

Leather Jacket

From L-R: Topshop Rosa Biker Jacket (sale! $58), Hinge Leather Moto (sale! $199), Treasure & Bond Convertible Leather Jacket (sale! $219)

Fashion Sneaker

From L-R: Nike Pre Love O.X. Sneaker ($80), Puma Basket Heart Sneaker (sale! $63) Air Jordan 1 Sage XX High Tops ($160)


From L-R (clockwise): Eileen Fisher Ives bootie (sale! $159), Isabel Marant Dacken bootie ($560), Blondo Verona Waterproof (!) bootie (sale! $99)

Day to Night Dress

From L-R: ASTR the Label button front dress (Sale! $52), Sea Weatherly Dress (sale! $217), J.Crew Point Sur v-neck ruffle knit dress ($138)


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