Dressy Casual Outfits For Three Days In San Francisco
What I Wore to a Content Creator Summit with 7 Stylish Bloggers
There’s a particular kind of pressure that comes with helping plan a conference in a city you used to call home. You want everything to be right.
San Francisco was home to me for nine years until four years ago. And when the opportunity came to co-plan a Content Creator Summit with Cindy and Annie, I pushed for San Francisco as our destination.
We wanted our fellow bloggers to leave having learned something, but also having experienced San Francisco the way I knew it.
Coming from my new beach town life in Florida, I hadn’t even started thinking about what to wear in San Francisco for three days. But I was excited to pack for it using what I already had plus a couple of new additions.
The Packing Reality: A Medium Suitcase
Packing for San Francisco requires thinking about the weather. I knew I’d want my lightweight wool coat for evenings and I also packed a raincoat (incidentally, you will probably want a raincoat in Summer too with the fog).
Those two coats alone meant I checked a medium Quince suitcase and not just a carry-on. It’s a great lightweight bag. AND I had room for a few Sézane purchases on Day Three (recap about that here).
Day One: The Ferry Building + Dinner at OneUp
Pulling up to the Grand Hyatt Union Square felt like a homecoming. Union Square is in the center of San Francisco — walkable to almost everything. It was also the perfect base for everything we had planned.
After checking in, Cindy, Annie, and I did what any sensible person should do on their first afternoon in San Francisco: we walked to the Ferry Building, a beautifully restored historic terminal lined with local food vendors, artisan producers, and some of the best casual eating in the city.
For Day One, I needed a dressy casual outfit for San Francisco that could handle a brisk afternoon walk along the Embarcadero and then transition to dinner just by putting on black booties.
- L’Agence cropped jacket, well made and feels chic. I bought a size 4 for a fitted look
- Banana Republic white tee (new, something about a fresh tee gives you a boost). Sized up to medium
- Mother Flare jeans
- My existing silver bracelet jewelry by David Yurman
- Black booties (similar)
- The black crossbody that I actually took was by Quince
Dinner was at OneUp Restaurant, right in the Grand Hyatt. We decided to choose the hotel restaurant for night one as everyone is tired from travel, no one wants to coordinate a rideshare across the city, and you need the first evening to feel easy and welcoming.
Day Two: Conference Room, the Neiman Marcus Rotunda + Chinatown
Day Two was the hardest working day. We had a very full agenda that Cindy devised for us to cover.
We spent several intense hours in the conference room. I want to say that this was the heart of the summit. The group engaged so enthusiastically that I, as the moderator, often had to vocally steer (ie. shout) so that each person was given a chance to be heard. Next time, I will lay out better ground rules 🙂
For a day spent mostly seated in a professional setting, I needed a dressy casual outfit that looked polished in photos but was comfortable for hours of focused work.
- cropped Veronica Beard jacket (a couple of years old) similar here
- Hermés silk scarf that Howard gave me years ago (similar) inspired the whole outfit and made me want to match with the booties
- fresh black Mango tee shirt
- J. Crew trouser jeans
- Quince triple compartment leather tote in stock in cappuccino (and a Quince quilted black leather crossbody)
- black leather belt
- Older comfortable suede block heeled booties (similar)
Lunch At Neiman Marcus Rotunda Restaurant.
Then we broke for lunch to walk to the Neiman Marcus Rotunda Restaurant. (Thank you Annie for making all the restaurant reservations).
If you’ve never been, the Rotunda is one of those only-in-San-Francisco experiences that visitors sometimes miss because it’s tucked inside a department store.
Here I am with Jennifer from A Well Styled Life. The afternoon brought us back to the summit for more work, and by evening we were ready for something completely different.
We took the group to R&G Lounge in Chinatown for a family-style dinner. R&G is a San Francisco institution — beloved by locals, delicious and unpretentious in a way that felt like a perfect counterpoint to the Rotunda lunch. We walked through Chinatown and experiencing it on foot — the lanterns, shops, the energy of the streets …made enduring a little rain worth it.
I didn’t want to get soy sauce on the white jacket so I switched to a Veronica Beard striped fitted tee and Vince navy cropped sweater jacket on top. I also wore the striped tee and cardigan jacket with above the light wash AYR jeans (my favorite jeans and Annie’s too) and pretty blue Adidas on the airplane home.
Footnote: My friend, Mercedes bought light wash AYR jeans, too and was wearing them last night (her new faves, too).
Day Three: Sézane on Fillmore + Dinner at Kokkari
If Day Two was the hardest working day, Day Three was the most fun! I wanted to wear something a little dressier that would take me through the day and into the night.
- Veronica Beard knit navy dress with Sézane dark brown belt
- Dolce Vita dark brown boots on sale but almost sold out.
- Madewell older silk bandana (this inspired the whole outfit too). Pull out your old scarves again.
- Dark brown J. Crew cashmere cardigan – sold out, other colors here.
- Theory double sided wool cashmere coat. Also sold out. I bought it last year. Quince has a similar one that my friend loves.
Kokkari is one of San Francisco’s most beloved restaurants — a stunning space with exceptional Greek cuisine. For a closing dinner, it was exactly right: beautiful, warm, and little dressed-up. Around the table and on the walk home, I felt like Cindy, Annie and I had achieved a successful gathering.
Here I am with my new Sézane straw bag.
I had a planned for us to take the Hyde/Powell cable car from Union Square (past where we lived on Russian Hill) down to Fisherman’s Wharf. But everyone was too mentally exhausted (me included). But now we have something for next time 🙂
The Quick Packing Breakdown for San Francisco
For anyone planning a similar trip, here’s how the suitcase came together:
- Coat: Lightweight wool coat + raincoat (but realistically, I could have just used one raincoat)
- Outfits: Three core dressy casual looks built around mix-and-match pieces — jeans/trousers, a skirt or a dress, layering tops (like fresh tee shirts), two jacket/blazers and a cardigan
- Shoes: Three pairs maximum — a comfortable walking shoe, a heel or elevated flat, and one pair that could do everything in between
- Accessories: Scarves are BACK. One bag, simple jewelry.
A huge thank you to Cindy, Annie, and all of our incredible bloggers for making this summit everything I’d hoped it would be. San Francisco, as always, did not disappoint.
Check out what Annie and Cindy wore over the three days:
Most Lovely Things
Cindy Hattersley Design
Have you visited any of these San Francisco spots — the Neiman Marcus Rotunda, R&G Lounge in Chinatown, Sézane on Fillmore Street, or Kokkari? I’d love to hear about your San Francisco favorites in the comments below.
Shop The Post
Perfect packing, MA! A++. I love everything you wore, but the L’Agence and Veronica Beard cropped jackets are the creme de la creme. I also adore the VB dress you wore to Sezane … stunning. So glad you bought the straw tote, and it worked perfectly with the dress. I was happy to see the Quince tote in person, I’m going to finally pull the trigger so thanks for the link. You, Cindy and Annie hit it out of the park on this conference. I know we were a little rowdy and unmanageable in our all day session. That said, it just showed how enthused we all were to be there and barely able to contain our excitement. You were an excellent moderator. xoxo
Great post! I used to attend a conferences in early December during the mid nineties in SF. We would lunch at the Rotunda and do a little Christmas shopping. It was so popular we would make next year’s reservation while we were there. We would go to Chinatown for dinner and shop there. I remember buying a tablecloth there. Maiden Lane was so charming, cute cafes in the street and unique shops, not a designer shop in sight. We’d go to Gumps and Williams Sonoma and Nordstrom’s. The Coach store was one of my favorites. We’d go to Kuletos and Postrio for dinner. Fun times. San Francisco was absolutely magical then.
Mary Anne, So enjoyed your post!
There is a woman in your group I don’t know.
She is blonde with wire rimmed glasses.
Her blog?
Please give us details on styling your hair.
What do you ask your stylist to do, when cutting or styling?
Color? (Not to insult you)
Blow dry?
Curling iron?
Flat iron?
Details, lady.
Please and thank you!!!!!!
That’s Jennifer. I put the link to her blog under the photo where she shares lots of good info!
Love your outfits!
Thanks, Annette!
What a great post! You look fabulous in all of your outfits! I love traveling vicariously with you! I can’t believe that it’s been since 2010 that I’ve been following you! Time flies💕
Thank you, Nancy!!
Mary Ann! What fun we had in SF!! I loved every one of your looks! Your jacket with the blue sneakers to your Veronica Beard knit dress! I can’t wait for our next summit!!
I know, Annie, we will have to do it again!
Mary Ann, the new blog looks beautiful! As do you in all of your outfits. If I had to pick a favorite…the blue dress and the brown boots. Perfection.
Have a wonderful week.
Thanks, Elizabeth!
So fun reliving the conference through your post! Enjoyed it so much!!