San Francisco is never going to get unbearably cold, so don’t bother packing a hulking marshmallow of a parka with a fur-lined hood. You will be extremely annoyed about carrying it around all day and it will be too puffy to tie around your waist. Instead, opt for a lightweight jacket with a hood that is large enough to shield your face from the occasional drizzle but light enough to fold and store in a backpack.
A layered wardrobe is the key to being comfortable on your San Francisco excursion. Start with a tank or t-shirt and add at least one extra thin layer before choosing the right jacket. I emphasize slim and manageable fabrics because there is nothing worse than feeling like an over-stuffed sausage. There will be multiple times in a day when you will want to quickly add or remove a layer so keep it simple. Zip-ups, button-downs, and wrap styles in thin fabrics like cashmere and chambray add warmth without adding volume.
Sunglasses and hats
This city gets a generous bit of cloud coverage and it’s rarely scorching, but if you are walking around you will want to protect your face and body from the blazing midday sun. Apply and reapply a high SPF sunscreen throughout the day. Neutrogena spray sunscreens are great because you don’t have to rub them in and adding more later is effortless. I also highly recommend an appropriate hat to keep the heat in or the sun off. One of the most dapper shops in San Francisco is Goorin Bros, a flagship haberdashery in North Beach. You will find shelves and shelves of mens and womens straws, wools and flat caps of the highest quality and craftsmanship. Finally, you will need sunglasses at all times. You will need them to shield you from sun, obviously, but you will also need to use them like aviator goggles when the wind kicks in and carries a smart car dangerously close to your retina.
Having the right socks and shoes should be your number one priority when you visit San Francisco. I’ve seen far too many poor souls traipsing these harsh streets in sub-par footwear that is basically ruining their entire experience. When your feet hurt you cannot think or care about anything else and you certainly can’t enjoy this fair city. Avoid such drudgery by packing a pair of comfy weightless sneakers, padded socks, and sturdy leather boots for going out at night.
You are going to want to carry a lot of stuff with you on your City by the Bay adventure. Don’t struggle with hauling around a heavy purse or messenger bag when you can select a comfortable and fashion-forward backpack instead. Opt for styles that are roomy enough inside for a few extra clothing layers, water bottles, a fold-up umbrella/rain poncho, and sunscreen. Try not to store anything important in the outer pockets and be sure to move your over-stuffed backpack to your front if you are traveling on jam-packed MUNI or BART.
The gloss-free zone
One of the rookie mistakes I made when I first moved to San Francisco was wearing lipgloss. I would step out of my house and instantly become entangled in a whirlwind of my own hair and street garbage, and my lipgloss was the glue holding it all together. Another time I pulled my hair back, popped on what I thought was a non-sticky gloss, and decided to take a casual bike ride downtown. Not even 10 minutes into my ride I felt like I was slapped in the face by an invisible assailant. I pulled over to the sidewalk and took a look in my compact mirror. There was a bug stuck in my gloss and its legs were still moving. Don’t be like me and risk wearing lip gloss in this windy city. Nothing good can come from it.
One last suggestion…
Nothing makes you look more like a tourist than sporting any type of San Francisco, Alcatraz or Golden Gate Bridge paraphernalia. I get it, it went from 75° to 40° in five minutes flat and you need another layer of warmth or your vacation is ruined. But rather than settling for a $60 hoodie with a typo, call a lyft and get yourself to Union Square where there are hundreds of snuggly options that won’t get you sneered at or preyed upon. Uniqlo and H&M are across the street from one another and offer tons of warm clothing that is affordable and that you might even want to wear again! In the same vicinity you can also find Macy’s, Forever 21 and the Westfield Shopping Center, great solutions if your clothing or shoe choices didn’t go as planned.