Halfdays history in the making: our takeover of the Million Dollar Cowboy Bar

BTS of how we rebranded one of Jackson’s most legendary institutions into the Million Dollar Cowgirl Bar

Aug 28, 2025

From the start, part of our vision for Halfdays has been to celebrate the culture of the mountains – not just the sport. Skiing is fun, yes. But what makes it magic is the whole world around it: the trips with friends, the après, the outfit planning, the bars you stumble into with your ski boots still on.

So we asked ourselves early on: if fashion brands can collab with Ritz Paris (FRAME) or Katz’s Delicatessen (Madhappy), why can’t an outdoor brand partner with the institutions that actually define mountain town culture? Why can’t we celebrate the places skiers actually love – the ones with history, soul, and a few scuffs on the dance floor?

At the top of our list: the Million Dollar Cowboy Bar in Jackson, Wyoming. If you’ve been, you know – it’s an iconic spot. Saddle barstools, live music, neon lights, and decades of Western lore baked into the wood. It’s where my co-founders and I have ended every night out in Jackson, and where we dreamed of one day seeing Halfdays come to life.

It didn’t happen overnight. The Cowboy has been family-run for decades, and with that comes a deep pride and protection of the brand. It’s an institution with history, legacy, and a name people travel the world to experience – so the idea of letting an outside brand come in and tweak it wasn’t an easy sell. We pitched, re-pitched, and pitched again. For almost a year. And finally – we got the green light to do what no one had done before: rebrand the Cowboy for one night as the Million Dollar Cowgirl Bar.

And yes, we’re all still screaming about it.

We celebrated with a Ladies Night that was part old-school Western, part Halfdays spin. Brandi Cyrus DJ’d. Our community showed up in boots and fringe. And of course, we dropped a full merch collection – tees, sweatshirts, hats – stamped with Halfdays, Wyoming. You can still grab it at the bar, or online at halfdays.com.

This was more than just a party. It was proof of concept: that outdoor culture can be celebrated in cool, culturally-relevant ways – just like fashion and beauty have been doing for years. And this is only the beginning.

Now here’s the play-by-play of our visit to Jackson:

Tuesday

My co-founder, Kiley, and two of our marketing team members, Andie & Sophie, flew in early to shoot the campaign for this product launch. They crushed per usual.

Special shout-out to our co-founder Karelle for showing up to shoot at 6:30 with her horse. Yes, she showed up with her real-life horse in Jackson’s town square at 6:30 am.

Wednesday
I arrived in Jackson and checked into the historic Wort Hotel – a western classic in its own right. That evening, we kicked off the trip with happy hour at the hotel + a very chic dinner @ Glorietta to welcome all of our lovely collab partners: Emon, Payton, and Kristen.

Thursday
To kick off the celebrations, we spent the morning on horseback, riding through Spring Creek Ranch.

That evening was our main event: Million Dollar Cowgirl Bar Ladies Night. Starting at 5:00 pm, the Cowboy was ours. It was the most iconic evening. The place was totally packed – we had over 400 people show up. Brandi Cyrus DJ’d and we danced for hours. There was a branded photobooth, free drinks sponsored by Wyoming Whiskey, and a Million Dollar Cowgirl mug for everyone that walked through the door.

Friday

To reset, we hosted a morning yoga flow and then gave ourselves the day to relax. We had lunch at Persephone and dinner at Snake River Grill – which may have been my favorite meal of the trip.

To close out the weekend, we all hit the Jackson rodeo – as any cowgirl would.