I always travel with one suitcase and one tote bag, that’s it. I find managing more pieces, even if they’re small, leaves me feeling uncoordinated and harried. Travel is already discombobulating, no need to make things worse!
I’m actually better about packing my carry on than my suitcase. I only bring what I need, even going so far as to downsize into a smaller wallet since on most trips I’m unlikely to need my Costco card, my ski pass, etc. etc. Most things I carry in my purse every day: wallet, phone, keys, sunglasses, pen, small pouch with grooming necessities, business cards (hey, you never know!), and travel umbrella (I picked this particular habit up in London and it’s saved my butt a couple of times since). For a trip, I add my passport, headphones, jewelry pouch if I’m bringing any, iPad and Kindle, assorted chargers/converters, my latest needlepoint project, and a small cross body bag to use at my destination.
I do carry on in a regular tote – the small Goyard is a great size, quite lightweight, goes with everything, and I like that I can used the attached pouch to keep my phone within easy reach. I don’t see the point of keeping travel-specific totes that would just take up storage space at home (remind me to rant another time about the ludicrousness of travel-specific stuff in general!) and I prefer not to call attention to myself as a tourist via use of recognizable travel prducts. All that said, carrying a decent amount of stuff on one shoulder throughout a long travel day does get old.
My husband swears by using a backpack as a carry-on for comfort and functionality. For him, it’s easier to stay organized if he has a small pocket for each object rather than a potential black hole of stuff. However, he’s a dude, and it’s a brave new world full of techie dudes who carry backpacks instead of briefcases daily: he doesn’t necessarily look like a tourist!
I must admit, the carry-on bag is one of those places where I sacrifice a little function for form. It’s not the first, and it certainly won’t be the last!