What I Packed for a Creator Conference in San Francisco — Outfits & Packing Tips

Mary Ann, Annie and I just returned from a three day conference in San Francisco. Let’s chat about What I Packed for a Creator Conference in San Francisco — Outfits & Packing Tips.Real outfits, real lessons, zero overpacking regret, well almost!

San Francisco skyline from the Grand Hyatt Union Square

The view from my room at the Grand Hyatt Union Square SF. If you are traveling to San Francisco I would highly recommend it. Great location steps from Union Square and an easy walk to many locations.

What I Packed for a Creator Conference in San Francisco — Outfits & Packing Tips

I’ve attended a lot of events over the years, but there’s something uniquely high-stakes about packing for a creators conference. You want to look polished and like yourself( not like you’re trying too hard) while also being ready to walk six blocks to dinner, sit through a full day of sessions, and network at a cocktail hour without looking frazzled. All in San Francisco, where rain was predicted and the weather can be extremely unpredictable.

Maiden Lane San Francisco

Think of this as your unofficial San Francisco packing guide for the conference circuit for those of us who care about looking intentional without spending the whole trip managing our outfits. If you’re searching for creator conference outfit ideas that actually hold up across a full day, you’re in the right place.

This is a full breakdown of what I actually wore over three days, what I packed and why, and the practical details I wish someone had told me before I zipped up my carry-on.

First, a Word About San Francisco Weather

I grew up in the Midwest hearing ‘the coldest winter I ever spent was a summer in San Francisco’ . My daughter lived in the Presidio Heights for a few years (beautiful but freezing).Even in late April, mornings can be in the low 50s, afternoons can climb into the 60’s, but the moment the fog (and the “breeze” rolls back in, that light jacket you’d stuffed in your tote is a non-negotiable. Oh and did I mention rain was predicted? Layering is more of a survival strategy than a style choice.

Jennifer Connelly and Cindy Hattersley walking to dinner in San Francisco

Yes it rained. Note those of us that have frizzy hair.

My 3-Day Creator Conference Capsule Wardrobe

I did a carry-on only even though I had the option of more since I was driving. My car was filled with conference booty (thank you Quince). Quince was kind enough to donate makeup bags and luggage tags for all of us.

creators conference goodie bags

Here’s exactly what made the cut and why.

The Foundation Pieces I Built Around

  • My comfortable Rag ane Bone Miramar jeans
  • My favorite denim trench/duster.
  • A fun pair of trousers from Spartina
  • A couple denim shirt jackets
  • My favorite Rag and Bone Military Blazer

Shoes: The Decision That Will Make or Break You

San Francisco is not a heels city, leaves those at home.I brought three pairs of shoes: white leather fit flop sneakers, gentle souls comfortable low-heeled ankle boot, and one pair of mules that I didn’t need.. The sneakers earned their carry-on square footage a hundred times over.

Accessories Did the Heavy Lifting

This is where I made my outfits feel like me rather than like a very sensible travel uniform. A few pairs of earrings (they weigh nothing), two scarves that doubled as layers, two handbags,a structured tote that held my laptop, a notebook, a portable charger, and still looked intentional, and my apple watch. That’s it. Accessories are where your personality lives.

Day-by-Day: What I Actually Wore

Day 1 — Arrival

Cindy Hattersley, Mary Ann Pickett, Annie Diamond at the Embarcadero

Travel day meant comfort first. White jeans, a denim shirt jacket with a red bandana, and white sneakers, and warby parker specs.I l wanted to be comfortable but pulled-together. The evening mixer in the hotel bar was casual, so there was no need to change.

Day 2 — Full Conference Day +Lunch & Dinner

the conference gang outside the Apple Store

Susan, Mary Ann, and me on our way to lunch. I am wearing a denim shirt, great pants from Spartina,mules and a fabulous gifted daily bag from Parker Thatch (love their bags),Raen sunnies (my favorite), and a vintage native american pin (similar here).

The gang after lunch at Nieman Marcus, and at dinner R&G lounge (great suggestion Mary Ann).

color consult with Susan Blakey

Our friend Susan is a color consultant and she graciously agreed to do a quick color consult for a few of us (sorry for the scary photo no makeup but I did slap on a quick lip color post consult). Can you guess what season I am?

Day 3 — Workshops + Trip to Sezane

selfie at Grand Hyatt SF

The only selfie I managed to take (I am a poor excuse for an influencer) Comfort and practicality were the whole mandate. I am wearing my Rag and Bone Miramar Jeans , Rag and Bone blazer (old, similar here), (this years version is shorter here) low heeled booties. gifted Tory Burch bag (love the color and a really old scarf. Warby Parker glasses frames.

Sezane shopping trip creators conference

Noelani from La Vie on Grand, Kim from Northern California Style, Juliet from Make Mine a Spritzer, me, Jennifer from A Well Styled Life,Mary Ann from Classic Casual Home and Susan from Une Femme Susan Blakey. I can’t imagine a better group. We had so much fun but missed our friend Kris from Driven by Decor, and Elizabeth from Pine Cones and Acorns who could not attend. All of these ladies have wonderful blogs. I highly recommend them if you haven’t checked them out.

Noelani arranged a private shopping event with the new Sezane on Fillmore Street. As you can see all of us got into trouble! If you are in the city I would highly recommend stopping by. I purchased this dress, and these pants, and this shirt.

What I Packed Beyond the Clothes: Content Creator Travel Essentials

The style side gets all the attention, but here’s what was actually essential for three days of conference life as a content creator:

You might enjoy my post How to Rock an Over 50 Travel Wardrobe-Hawaii here

The Honest Networking Outfit Advice Nobody Gives You

Conference dressing advice usually focuses on looking impressive. What it doesn’t say enough: wear something you feel good in at hour eight. Because by hour eight, you’ll still be ‘on,’ still having conversations, still being photographed in the hallway, and if you’re in shoes that are hurting you or a waistband that’s gotten tighter as the day progressed, it shows.

Confidence at a networking event is partly personality and partly logistics. If your outfit is working against you, you’re spending energy managing it instead of being present. That’s the part I’ve learned the hard way, and the reason comfort is now a non-negotiable criterion alongside aesthetics when I’m dressing for anything that matters.

For women over 50, this realization tends to come with experience, and I’d argue it’s one of the genuine advantages of being at this stage. Knowing that ‘polished, comfortable, and completely yourself’ is actually the best version of dressing well takes more intention than just grabbing something that looks good on a hanger. That clarity is worth something.

What I’d Pack Differently Next Time

  • One fewer ‘just in case’ outfit. I brought four complete looks for three days and of course wore three of them. The fourth sat in my bag untouched. It always does.
  • Dry shampoo in my tote, not my suitcase self-explanatory. Humidity or rain in our case, and conference days are a predictable combination.
  • Fewer shoes — always my downfall, and I never learn. The ankle boots and the sneakers would have covered everything; the mules were a luxury I wore almost exclusively in a climate-controlled conference room and on a very short walk to lunch.

The Takeaway

A creators conference asks a lot of your wardrobe. It’s not one environment several: airport (in my case the drive), sessions, lunch, cocktail hour, dinner, and the unexpected. The outfits that serve you best are the ones that transition without requiring a full change, that look like you, not like a version of you that’s trying to look like a content creator.

Bring fewer pieces. Make sure each one works with at least two others. Pack a layer you’ll actually reach for. And wear your most comfortable shoes to everything except the one event where a block heels genuinely feel worth it. That’s really all there is to it.

If you are traveling to SF you might enjoy San Francisco Travel’s website here. San Francisco gets a bad wrap. It is a wonderful city.

Thank you for reading What I Packed for a Creator Conference in San Francisco — Outfits & Packing Tips..We will be heading to France at the end of the month, and I hope to perfect my packing! Any packing tips you would like to share? I would love to hear about them.

Now let’s pop over and visit Annie and Mary Ann for their travel tips.

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25 Comments

  1. Great post! It reminds me of when I was working (retired 10 years now) and would attend three to five meetings/ conferences of 3 to 5 days a year. I quickly learned to mix and match and never wore uncomfortable clothes. I found knits to be more comfortable than structured shirts. Our days would last through dinner and drinks in the bar till midnight. When I did get a chance to change I would put on a long black sleeveless knit dress and add a cardigan. It was like wearing a nightgown but looked very polished. I never wore jeans, I found them uncomfortable then but I wear them now but only the pull on kind, no zippers or buttons. It’s not difficult to find stylish but comfortable clothes. And I love scarves, they really finish an outfit. And I learned from Susan the concept of tabletop dressing, the top is what most people see and remember.

  2. Dear Cindy!
    I am so envious..A wonderful trip to fabulous San Francisco. Loved your comments about what you learned. We always overpack and yes – shoes are the biggest issue. Valuable takeaways and thank you for sharing! Love the group picture – I follow Susan as well. BTW – I just bought a red dress to try and replicate your recent capsule along with a cool wicker purse. As always, thank you for your inspiration, Anna in Arizona! 🌵

  3. What an interesting and fun blog! It looks like you all had such a great time and being drawn to color, I loved that you were identifying your absolute best colors…it sure helped me 20 years ago. Your selfie outfit was one of my favs and it was such a great picture. Thank you for all the helpful information.

  4. Hi Cindy – just joined your blog from Marlborough New Zealand. (We are famous for our wine production). Love your style and came up on you by accident really….its great to see older women looking so stylie – I am 73 and still like to look well put together. I find I am not a great fan of sneakers (always feel disappointed in them for some reason) and tend to prefer ankle boots. If you can recommend your best ever sneaker that would be great. Sandy

    1. Hi Sandy

      Welcome! Your wine region is on our bucket list!! I have several New Zealand readers. I have had a hard time joining the sneaker crowd as well. I still am not a total fan with dresses (on me). I do like them with a casual skirt and cropped casual pants. My current fave for leather is https://go.shopmy.us/p-51623346. Super comfortable and accomodates the bunion! I love this olukai option for Summer https://go.shopmy.us/p-51634006. For walking the dog etc I am a new convert to this shoe https://go.shopmy.us/p-51881891. It is a slide in which is handy!!

  5. I’d say you are a “Winter”. I’m glad they are still doing color consulting. I had mine
    done many years ago and it completely changed the color of my clothes and makeup.
    Especially my lipstick!

    1. Hi Von

      I had mine done many years ago by a dear friend who has passed. She felt I was an autumn as does Susan. I find with my white hair I like many of the winter colors as well.

  6. Hi Cindy. The link for the dress you bought at Sezane goes to the home page for the store. I’d love to see which dress you bought. I love the other items that came home with you!
    It’s been so fun reading about this conference. I’ve been following 6 of you for years.

  7. You were in my hometown! Even though I haven’t lived there in many years, I still carry extra layers in the trunk of my car just in case. It looks like you had a wonderful time.

  8. Loved this. Yes, I always packe too much. I was amazed tht everyone seemed to wear jeans. Interesting. I’ve got to gt my jeans up to date. I want to try those Rag & Bones style. Wonderful that you all got togthr. I’m going to try and do that with some Mature YouTubers. Great idea. I would have loved to be a fly in the room and hear what you all talkd about.

    1. Hi Sandra!

      You should totally get together with your youtube buddies. I love my rag and bone miramar jeans. I just ordered another pair!

  9. Cindy So enjoyed comments on your conference. San Francisco weather is so unpredictable! I was stationed there a year and learned about umbrellas always, raincoats, and good shoes. I can’t imagine now how many miles I put in walking up and down those hilly streets! to go to my favorite places in Chinatown and the Ferry Landing and also the big department stores. I will always remember the huge fresh flower displays, strong coffee that come from beans arriving daily on the ships, glass counters of giant pearl strands, lux handbags, and the giant Williams and Sonoma which is gone now . Thank you again for sharing! Donnie

    1. Hi Donnie

      SF has suffered post covid, but it is coming back!! I miss the street vendors selling flowers! The picture of Annie, Mary Ann and I with a glass of wine is in the Ferry Building. We had fabulous food in Chinatown and at Kokari which I failed to share. I am glad it brought back fond memories for you!!

  10. Such fun to follow you ladies to your conference in SF! Could you please correct the link for the blister pads. It currently goes to the gift bags on Amazon. Unfortunately the skin on my aging feet is becoming very thin and susceptible to blisters… no matter how broken in or old the shoes are!

  11. I am going to London in May, and I will spend most of my time touring around art museums. I was wondering if the travel wardrobe for San Francisco would work for my London trip.

  12. What fun! I would love to hear the conversations you creatives shared. You all looked fabulous!
    And San Francisco always has been my favorite city in the world…. I left my heart there many years ago.
    I bet you’re a Winter…..

  13. The same hints go for traveling to Seattle, only prepare for more rain. Always enjoy your fashion cues. This has nothing to do with this post, but thank you so much for turning me,and other reader’s I’m sure, to Quince. I first thing I ordered from them was the denim chore jacket. Yesterday I just received their European Linen sleeveless swing dress in the color Chili. The clothes are so reasonably priced and look so expensive. Again, thanks!!!