Cabo dispatch

And a moment of appreciation for Gap.

Aug 20, 2025

Hi! Sorry this is coming to your inbox a day late (some of my flights were rescheduled due to the Air Canada strikes)!

Gap has been back

If you haven’t seen the new Gap ad, it’s pretty iconic. I’ve been saying for a while that Gap is officially back. Their clothes are great, lots of 100% cotton items, really clever brand collabs (Doen, Malbon, now Beis), and their ads have been crushing it. I loved the Parker Posey one at the height of White Lotus and this better in denim one with Katseye after all that Sydney Sweeney AE drama… so so good and excellently timed. It feels so authentically Gap.

Obviously the entire industry is being hit by fast fashion, and Shein and Amazon have completely changed what the economics of clothing are. But this is exactly where heritage brands can carve out a new lane and thrive: brick-and-mortar experiences (cc: Skims), good products, and storytelling that feels authentic instead of forced. Gap’s proving it can be done.

The thing is, I’ve always loved Gap, even when it slipped into cringe territory. There was a stretch when it was considered mall-core in the worst way but I still found myself going back for their basics. The quality never really faltered, especially when you consider the price. That’s why this moment feels so satisfying to me: the brand is finally syncing with a sharper cultural read.

📍Chileno Bay

We hadn’t been back to Cabo since maybe 2014 and wow, I forgot how much I missed it. Getting there from the East Coast is no joke, but we knew we wanted to head west so we could bring the kids along on a work project at Pebble Beach where we were doing a collaboration with Porsche. (Gull debrief in the next newsletter about what it was like to bring my kids on a work trip but to summarize: it wasn’t smooth sailing.)

We stayed at Chileno Bay, an Auberge property, and I have to say: they really have it dialed in. Comfort stations on every few holes of the golf course, incredible amenities… I didn’t realize Cabo was such a golf destination but it makes sense now. I’d honestly consider moving west just to make Cabo weekends a regular thing.

The heat was intense but the whole stay was dreamy. The only downside was the prices, very New York vibes. $40 breakfast items were the norm. Still, totally worth it, and the beaches were so gorgeous (and seaweed-free). We were there for four nights and for once, I actually wanted two more days. Usually by day four at a beach I’m itching to leave because I get bored, but not this time. This was the exact recharge we were looking for between late Vegas nights and a four day car extravaganza.