In a fit of boredom, I dug out all of my laptop/dual-use bags and cataloged them. Click on the photo to go see the larger version at Flickr.
Counter-clockwise from top left:
Land’s End Medium Zip-top Tote – heavy-duty canvas bag for toting random items between home and other places
Crumpler Chester Squander – Great laptop bag, I pack this when I need a serious “laptop + all accessories bag.” It’s kind of overkill for the new MacBook Air, but holds a 13-17″ laptop and all associated items easily.
Waterfield Designs Small Vertigo – This bag combined with their horizontal Sleeve Case was perfect for carrying my 10″ netbook + Kindle. Not sure what I’ll do with it now that I don’t have the netbook any more, but I can’t bring myself to get rid of it.
Timbuk2 Small D-Lux Bondage Laptop Messenger – My very first Timbuk2 bag, and my primary laptop bag. This particular color combo is discontinued, but the size is perfect for carrying my 13″ MacBook Air plus daily items such as lunch, wallet, sunglasses, etc. Alternately, I add a 3-section insert and pack my camera plus 2-3 lenses for a day trip, and still have room for the MacBook Air if needed.
Timbuk2 Xtra Small Custom Classic Messenger – A customized “Classic Messenger” with grab handle added, this is my daily bag. This size is perfect for my dSLR camera + lunch, wallet, and glasses. Just enough room for the essentials without being too bulky.
Belkin 8.9″ Messenger, brown – Tiny little tote for packing my Kindle (fits perfectly in the interior sleeve) and a few necessities.
Timbuk2 Xtra Small Classic Messenger – Same size, different color. For those days I want a small messenger bag but don’t want to carry a black bag.
Timbuk2 Small Classic Messenger – The basic, non-laptop version of the Classic Messenger. This one sees frequent use as a larger day bag, when I want to carry my dSLR plus a spare lens, lunch, and other small essentials to work or around the city.
Caselogic 13″ Felt Laptop Messenger – A slim, basic laptop bag that was a little small for my 13″ MacBook, but fits my new 13″ MacBook Air + essentials perfectly
Crumpler Considerable Embarrassment -The “big” laptop bag. This one holds “Considerable” stuff, I can fit my laptop, essentials, and a 3-section camera insert with my dSLR and a couple lenses.
No-brand Medium Tote bag – Peeking out over the back of the Crumpler, this tote bag is mostly used for holding other bags. It’s big and roomy and I can stuff a whole bunch of the other bags in to keep them organized
Timbuk2 Medium D-Lux Bondage Laptop Bag – A larger version of my other bags, this one is for those “one-bag” overnight trips when I want to get my laptop, essentials, and clothing all in the same bag.
Belkin 8.9″ Messenger, black – Same bag, different color. I liked the little brown Belkin messenger so much that I bought a black version too.
Disney Custom Denim messenger bag – A lightweight, formless messenger bag customized with my name and my favorite Disney character, this is a lot sturdier than it looks once appropriate laptop and camera inserts are added.
To see the camera inserts I’m using with my messenger bags, take a look at the Pile of Crumplers post on my photography blog.

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