I need a rolling briefcase!

a black and white suitcase with handlesAfter my last couple of day trips, it is very clear to me that I need a rolling briefcase. I just carry too much stuff in my purse for it to be comfortable, especially for huge airports like DFW. Even though I’ve been talking about getting one for almost a year, it just hasn’t been high on my priority list (like, say, shoes). But I promise you, here and now, I will have a rolling briefcase, that I love, before the end of May. Part of this is spurred on by the fact that I have three conferences over the next three months—my poor shoulders can’t handle the weight of my purse. Of course, one of the reasons I haven’t gotten one yet (and I know this will shock those of you who have read my blog for a while) is that I’m just too darn picky! I want all the features I need, I want it to be cute, and I want it for a good price. Is that too much to ask??

Here are the features I want:

  • Lots of space inside. Of course it will need to have room for my computer, files, and purse stuff. But it would also be great if it had room for me to stick a change of clothes in for overnight trips. I often feel silly bringing my normal suitcase on a trip when it’s only half full.
  • Outside pockets. Internal space is important, but I need to have a pocket on the outside where I can stick things I need immediate access to—my keys, phone, boarding pass, and lipstick.
  • Sturdy construction. While I love my existing purse and my suitcase, I am rough on them. They get stuffed to the brim, shoved in tight spaces, rained on, dragged, and dropped on occasion. I need something that will hold up to serious wear and tear. Also, because I will likely set stuff on top of it, I need something that is pretty square—not just a purse on wheels, like so many of the rolling briefcases marketed to women.

Here are two of the ones I’m considering:

This houndstooth rolling briefcase by JKM and Company  (pictured above) is really, really cute. It looks to have plenty of pockets for clothes, files, a computer, and purse stuff. It’s also nice and square, and has good reviews. Plus it’s under $100!a blue and black suitcase

I also love this McKlein USA Willowbrook Detachable Wheeled Briefcase. It comes in six different colors, is leather, has two main pockets, and it’s detachable if you don’t need the wheels! It’s a little smaller than the houndstooth one, but I do love the turquoise… It’s available from eBags for $206 and Amazon for $158.

Readers, do you have a rolling briefcase? What brand? Do you love it?

This post contains affiliate links.


  1. My wife used a Mcklein when she travelled and she found it be rugged with just enough “glam” to meet her aesthetic expectations.

  2. I know exactly how you feel. I am also incredibly picky about what I want. For me weight is very important because I have nerve damage in my shoulder so anything I have to carry – even if it’s just picking it up to carry up a flight of stairs needs to be light weight. I also didn’t want it to be too big or wide because if I have to carry it on with my roller board I don’t want it to be so bulky that it draws attention. I ultimately went with a lipault model which is very slim. After getting it, it works for my purpose but it was way more expensive than I wanted to pay and I doubt I could fit my laptop and anything else in it. There is this awesome luggage store in Seattle I stumbled upon when I was at a conference last fall called Bermans luggage that had so many great styles to check out in person. A lot of them are really heavy though or really expensive. I also was looking at the mcklein detachable briefcase because I thought the colors were cute but it is heavy and very stiff (hard to get things in and out of easily). good luck on your quest and let us know what you ultimately decide on.

  3. Briggs and Riley, every time, for both my partner and I. Tough, light, and a lifetime quibble-free warranty.

  4. I would make sure that the dimensions allow for it to fit under the seats of the planes. Too often I have a flight on a CRJ or embrair where the overhead space is so small that your only option is under the seat or gate check it. Not something I want to do with my laptop.

  5. I need one too… My laptop bag also holds so many other things besides my computer that it has gotten really heavy. The shoulder straps feel like they cut into my shoulders. :(. Please keep us updated on what you get in the end!

  6. I’ve had a Samsonite wheeled briefcase for years and it works really well for me. Not cute at all, but tough and serviceable. Has room for laptop, files, chargers etc, as well as a separate compartment roomy enough for clothing and necessities for an overnight trip.

    I’ve been able to fit it in the overhead on American Eagle Embrair planes. Just checked their website and they have a few models on sale right now.

  7. I’ve had a McKlein rolling briefcase in red leather for the last year. I’m on the road every week and it holds up to a lot of abuse. I would go for a quality product-It’s an accessory but i rely on it to look professional.

  8. Just saw a new product by Baggalenni – a lightweight rolling briefcase in fashion colors

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