How I Travel: The Bag Within a Bag

Today’s post is one that I’ve been meaning to do for a while, sharing how I normally travel with just a handbag/laptop bag, and a carry on suitcase. As many of you know, I absolutely loathe checking luggage (although I know that this is going to have to change with baby) and always try to travel without ever interacting with a baggage carousel.

My most important tool in my quest to travel lightly? The handbag within a bag! Unless I’m going on a short trip, you’ll never catch me at the airport with just a roller and a little gorgeous purse dangling off my arm. You are much more likely to see me instead with a trolley and what looks like a gigantic, stuffed bag on my shoulder. Inside that bag, is my actual “real” handbag – as well as a shawl, my laptop, water for the plane (purchased after security), snacks, my Kindle, and more. Doing so not only allows me to carry lots more than what just my handbag could carry, but also protects some of my favorite bags inside. The last time I went through the TSA Precheck line, they weren’t even letting people put their purses inside of a plastic bin – they all had to go on that very dirty rolling conveyer. I’m all for using and not babying my items…but subjecting your little box Kelly to that treatment without even a bin or bag to protect it, I’d say borders on abuse.

Here are a few of my favorite bags to use for traveling. I call them my “plane handbags” for that reason. I’ve picked them because they are each super light, fit most of my favorite leather bags well, and also quite a few other goodies as well. I’ve used both of these bags on multiple trips, by the way – and have never been questioned by aircraft crew about using them as my other “handbag” carry on.

The first is the old standby – the Longchamp Le Pliage. Here, it’s pictured with my 32cm Kelly inside and a shawl. It easily can fit a laptop in a padded case, my Kindle, a bottle of water, and some other goodies as well.

A size comparison on top of my Globe-Trotter carryon (my other frequently used one is the Tumi Alpha)- as you can see, the top of the Kelly handle peeks out here, as the bag doesn’t zip fully with it inside. Doesn’t bother me at all, but just something to note.

The Longchamp is one of my favorite bags (as it is for a lot of people). It isn’t the most structured, and I wish it had more pockets, but that’s really one of the genius features of the bag as well – it’s super light and folds up well. If you don’t necessarily your plane bag to fold up though, then I’d highly recommend looking into the Longchamp Neo as well – same dimensions, but a thicker, sturdier fabric that looks just a wee bit more formal and structured.

Another plus about either Longchamp (but especially the Neo)? They look decent enough to take to the office or meeting, which I’ve often opted to do in circumstances where I’m dragging my laptop and papers around, and/or having a designer bag isn’t appropriate.

Now, I’d like to show you an alternative “plane handbag” – the Kipling Sasha.

The Sasha isn’t as sleek as the Longchamp options, but I’ve found it to be quite a bit more practical at times. First of all, the bag comes with a long strap which can easily be shortened or lengthened to be crossbody – always a plus when running around a new city! As you can see, it also fits my Kelly with lots of room to spare. There’s a large zip pocket inside, which just fits my 13” MacBook Air without a sleeve – I usually don’t use it for that purpose.

As I mentioned earlier, the Sasha isn’t as “clean” a look as the Longchamp options, and can’t be used in a business meeting. But what the bag lacks in looks, it makes it for in other areas. I love the multiple pockets in the front, as well as the long zip. Often, I’ll stick my passport in one of the front pockets for easy access, along with a pen and my wallet.

And, one of the best features?

Yup – it slides over your suitcase handle easily! I can’t tell you how many times I’ve attempted to put my Pliage or another tote like this on my suitcase for easy rolling, only to have it tip over or fall off. Not a big deal, although it can get seriously inconvenient when you’re running to catch another plane or trying to balance everything you’re lugging. You’d never think this little bit of fabric would make such a difference, but it does. Plus, for other mamas – the Sasha makes a good diaper bag too, and you can adjust the cross body strap to hang over the handles of a stroller.

I do have some bags larger than the Kelly 32cm, and for those I also own the Kipling Ferra, which is a few inches higher. The Ferra fits my Bolide 35cm and also used to fit my Birkin 30cm easily, and could zip over both. It doesn’t feature as many pockets as the Sasha or the cross body strap though – just something to keep in mind!

I hope this post has helped some of you who have been looking to for ways to travel without checking baggage…or who just want to protect your expensive bags while traveling! And if you have any “bag within a bag” recommendations to share for fellow travelers – please do, I’m always looking for new finds, as I’m sure other readers are too!