I collect many things — including nice bags.
I love having an assortment of bags available to me. It not only presents the opportunity for a unique configuration for each trip I go on (either the "trip" of the day, or a business trip), but it also allows me to feel at home wherever I am — which is very important to me. There's nothing more important to me than feeling at home, especially when I'm on the other side of the country (or in an office).
The Tibeca Slim Leather Biefcase by Bosca is my daily-carry biefcase. It's a wonderful bag, that holds many things. I particularly like its doubled handles.
Mine sports a WWII screw-back Caduceus pendant in the center front. I use it without the strap (though I carry the strap inside, just in case).
Price: $475. Worth every penny. There are certianly cheaper biefcases out there, but this one should last a lifetime.
The Dolce Double Compartment Flapover Brief by Bosca is my "I need to carry a ton of things" messenger bag. It comes with a great shoulder strap, and doubles as a (single–handled) briefcase, if needed.
The extremely nice leather of this bag (which smells incredible) prevents me from customizing this bag. I'll get around to it, eventually. I like that it has a "stock" configuration, though.
Price: $795. Also not cheap, by any means, but again, it should last a lifetime.
The District MM Damier Infini Leather Messenger by Louis Vuitton is my every–day–carry bag. I always wanted to own a bag made by Louis Vuitton, but could never find one I liked. This, out of everything in their collection, is indeed the only piece I would ever consider owning (and do).
It is exceptionally well made, carries a legacy of an exceptional brand, and (most importantly) holds an iPad Pro 10.5" and all my Leica lenses perfectly, with plenty of discrete small pockets for accessories (like dongles and lens/glasses wipes). Overall, it is my favorite bag.
Functional, very body friendly, and soft to the touch, this is the perfect companion for everyday life. The supple Damier Infini leather makes it ultra-wearable and a myriad of compartments keep things organized.
Mine is customized with a few metallic pins on the shoulder strap: Pickle Rick (Rick and Morty) and a Digital Ocean logo pin. I love the constraints this bag puts on me. It forces me to really think about what I'm carrying for the day.
My backpack is an older rendition of the Alpha Bravo 'Knox' Polyester Backpack by Tumi. I've owned it for the better half of a decade, and it hasn't shown a single sign of wear. I absolutely love this backpack, as it continues to grow on me, and highly recommend it to anyone looking for a solid or unique backpack.
Mine is customized with an embossed Heroku logo, as well as some metal embellishments that have been permanently glued on it.
This bag isn't sold anymore, so the link below is to a Google Shopping result, which may stop working over time. You may have to hunt around for this bag.