We require a lot from our luggage. The right suitcase not only needs to look good and be easy to carry, but it also has to do a damn good job of keeping everything we've packed protected and organized. So we asked some of the most stylish travelers we know for the bags they rely on when leaving town.
I travel a lot (125K+ miles each of the past three years) and I always pack bags that go in other bags. Generally, I leave these smaller bags packed in between trips as to minimize packing time. I bought this three-piece Kelty x Beams set in my favorite color the last time I was in Tokyo. I use the big one as my "International Economy" bag (which I only bring when I am flying a redeye to Europe or to Asia in steerage). It holds a travel pillow, Nalgene bottle and a pair of Muji travel slippers (because you don't want to hit the highly trafficked economy bathroom in socks). It can also be used to pack a pair of shoes or hold dirty laundry on your return. The middle-sized bag is for electronic accessories—chargers, an international power converter and even a spare memory card reader. If I didn't always leave everything in this bag, I'd inevitably forget something. The smallest bag holds essential items that I always bring with me (in my under-seat carry-on which is usually this Filson briefcase). I carry hand cream, Advil, an eye mask, tissues, Purell, a toothbrush and an extra set of headphones. If you fly in first class you won't really need this bag as everything here will be provided, but it's nice to have the stuff you like, regardless of the cabin you're in.
I usually have to travel with two or three heavy bags because of all my photography and digital equipment. And my go-to bag is this hardside spinner from Samsonite. I don't know how anyone survives without a suitcase that has this kind of mobility and security. Plus, for the quality, it's extremely affordable. I've had the thing for over two years now and it still looks brand new.
$270, by Samsonite
I swear by Rimowa luggage. Made in Germany from aviation-grade aluminum, I love it because it's chic and feels at once both modern and vintage. I use the small trolley as a sturdy carry-on and then larger suitcase (complete with multiple mesh dividers to keep your stuff in place) for everything else. Having a matching set makes the process of packing more exciting for some reason.
29" suitcase, $1,130; Mini trolley, $980 by Rimowa
I prefer soft cases because I always seem to come home with more than I left with, so the expandable space is a blessing. Swiss brand Victorinox, originators of the Swiss Army Knife, makes some of the best out there—lightweight yet durable. Everything else, in my opinion, is crap and seems to fall apart after a few trips. The brand has a great lifetime warranty, and will repair rips and wear-and-tear for free, no questions asked.
$250, by Victorinox
How to Pack a Suit: Step-by-step instructions on how to ensure your suit jackets and blazers arrive wrinkle-free.