I have the same bag, and I'm a big fan. After three seasons of flying to ski trips, I've settled on this luggage arrangement which has worked extremely well for me.Here's what I do...
I have this bag : https://www.dakine.com/en-us/bags/travel-bags/snowboard-gear-bags/boot-pack-50l/
Wear:
- Walking boots
- Casual clothes
- Ski jacket
- Ski Boots (with multiple pairs of socks stuffed inside)
- Baselayers, Facemask, Ski Gloves, Goggles, etc.
- A few days worth of casual clothes
- Toiletries
- Skis, wrapped in towels for extra padding.
- Ski pants stuffed into side
- Ski poles
- Helmet
- Any extra baselayers or misc. clothing that's not necessary for the first day or two on the slopes