Stylish rolling bags to lug around your daily necessities

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Ultra Chic 18
Ultra Chic 18″ Quilted Rolling Tote with Laptop Compartment in blue.
In my new job, my office is in an inconvenient location, and I don’t like to drive from building to building around campus. Consequently, I find myself lugging quite a lot of stuff around with me throughout the day: books, papers, laptop, regular daily stuff.

Some of my colleagues have enormous box-like rolling contraptions that they use to cart their materials around campus. I’d prefer something that serves the same purpose but looks more stylish and less utilitarian. A rolling briefcase or suitcase could work, but I still want it to look interesting, unique, and pleasant (and I don’t want it to fall apart after a couple of weeks’ hard use).

That’s why I’m hoping for suggestions from Homies. Does anyone have suggestions for stylish rolling bags to lug around my daily necessities? -Maryr

Let’s pack it up and get a move on. Here are some of my favorite stylish, fun, and downright funky rolling bags for work, school, and every day life…

Olympia Deluxe Rolling Overnighter, in tulip.
Olympia Deluxe Rolling Overnighter, in tulip.



Solo Classic Collection Leather CheckFast Rolling Case
Solo Classic Collection Leather CheckFast Rolling Case

Kensington Contour Balance Notebook Roller Bag
Kensington Contour Balance Notebook Roller Bag

Leather Vertical Detachable-Wheeled Ladies' Briefcase in various colors.
Leather Vertical Detachable-Wheeled Ladies’ Briefcase in various colors.

Striped Rolling iPad, Tablet or Laptop Weekender Duffle Bag
Striped Rolling iPad, Tablet or Laptop Weekender Duffle Bag

Houndstooth 16
Houndstooth 16″ Rolling Canvas Laptop Bag Brief Case

Vaultz Locking Mobile Business Case
Vaultz Locking Mobile Business Case

Urban Junket Kristen Wheeled Bag
Urban Junket Kristen Wheeled Bag

Any other worker bees lugging fashionable work bags? What are you using?

Comments on Stylish rolling bags to lug around your daily necessities

    • Depends on your personal style. The whole Columbia/North Face/REI/LL Bean/outdoorsy look seems to keep wearing a backpack. Corporate chic goes to roll-y bags (or GIGANTIC leather(ish) laptop bag-purses). Confused academians end up with a beat-up briefcase, often in beige canvas. 😉

  1. Thanks for publishing my question, Megan! 🙂 And for doing the hard work of looking for some stylish and fun rolling bags.

    I’m of the confused academic variety, and I vacillate between corporate chic and cutesy/fun. My goal is usually to find something that reads “professional” but still lets me show a bit of my own personality. The last one on Megan’s list definitely fits the bill.

    I’m not a fan of backpacks for myself, mostly because I’ll look like a student (reference: OBH posts about looking too young), and I’ll still have to use a purse for my wallet, keys, and cards.

  2. Brilliant! Shoulder bags are starting to hurt my already-nearly-crippled from computer use arm/shoulder (don’t let this happen to you, young uns!) & backpacks don’t look great with my CorpGoth fashion sense (& really, when you carry as much crap as I do on pubtrans & walking to work, it’s still a back-ache, even w/an ugly & very practical backpack). I’ve been needing yet resisting a rolly bag, but dang, that stripey one is calling my name. A little pricy, but it’s an investment I should make instead of buying cheap bags & throwing them out when they break from overuse. Thanks! Saving for my next paycheck 🙂

  3. I immediately thought of Vera Bradley travel bags. Their smallest rolling bag comes in 22″ I’m afraid, but if you’re toting a laptop, plus books, plus lunch, the extra storage space might be worthwhile.

  4. I love these! I, too, have been experiencing major back/shoulder pain from an overloaded messenger bag, but hate wearing a backpack on the train (especially when I don’t get a seat–it just sticks out and gets in the way). I just wish that more roller bags came with an optional cross-body strap, for walking up stairs or uneven surfaces. And is big enough to carry books, folders, and lunch. Damn, I’m needy! I really want to buy one, but I just can’t find the right match for me. 🙁

    • I once had an unstylish rolling bag (really just a backpack on wheels). Another thing to keep in mind if you live in cooler climes: rolling bags are totally useless on snow-covered sidewalks! I live somewhere now where that shouldn’t be a problem, though.

      • Snow-covered sidewalks are probably the #1 reason why I want a crossbody strap and not just a tote bag on wheels. I’ve looked into rolling backpacks, but they are either too rugged or look too much like a high school backpack. I could do a backpack if it looked more like the black stipey bag.

        • Ugh, snow. We just moved close to my job so I can walk to work and these would be GREAT. I’m currently carrying my large purse on a crossbody strap and my paperwork in a large tote, but they are heavy and inconvenient. A crossbody strap on the tote is only going to make me look like a pack mule. A tote on wheels would be perfect (especially for picking up groceries after work), but I live in a super snowy area. Would a backpack on wheels actually work better than a tote? Should I just resign myself to pack mule status?

  5. I’m not sure this is entirely on topic, but these bags on wheels are so cool They are shaped like animals and you can pull them along, but they also function as a child seat so you can tow both your child and your child’s luggage through the airport or wherever whilst said child pretends they are riding a cow.
    Probably not desperately practical for professional use but still worth a mention under the heading ‘stylish rolling bags’ I thought.

  6. We accidentally bought* two Little Life Clownfish Wheelie Duffle bags for our nephew last month. I’d have LOVED to keep one for myself but the handle is a bit too short for me to use. However I’m 5’7″ (170cm) so if you’re a shorter person who loves fun animal themed luggage (or even – shocker – if you’re a child!) maybe you could rock one of these!

    *Over enthusiastic sale shopping!

  7. I recently did the Charlotte airport death march with an over the shoulder laptop bag, so I’m thinking if I ever do that again I want a bag that rolls. I’d rather not spend another $100+ dollars on a bag, and I want it to fit under the seat. That isn’t all that easy to find for a 17″ laptop. So before I buy another bag, I am going to try something else. I bought some small swivel casters at Home Depot and I am going to attach them to some luggage straps and put them around the bag. That way I can take them off so the bag still fits under the seat. I don’t suppose I’d do this for every day use, but I’m hoping it will work well enough for airports.

    • Please let us know how that works for you. I travel a lot (and live on the second floor in the snowy north) so I would totally steal your idea if it works!

  8. I highly recommend the Zuca Sport and Lifestyle rolling bag. It has a heavy duty frame that doubles as a seat, and the wheels will absolutely go through snow. There are a ton of fun options to choose from. I’ve used the same one for 4 years of heavy use at gaming conventions and in everday life. It has held up like a dream. A full size laptop will fit inside as well as several large books.

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