I'm finally feeling set in terms of suitcases and what I bring on a plane. I love my carry-on bag (I have the carry-on size) and use it whenever I travel for work. I love that the sections inside allow me to be better organized, and I always fit an amazing amount of stuff inside. I have the same bag in the checked-bag medium size, and love that for when we're going on a longer trip. These do get marked up when you check them, but I just use a magic eraser to get any marks off.
For shorter trips when we're driving, I usually use this weekender bag (also comes in a twill here) - it's so beautiful and looks way more expensive than it is. I had a crazy pattern one of these that Mia commandeered and I never loved the pattern but loved the size and functionality, so I was super excited to see it available in solids! I actually got the black color with a black monogram and it looks so chic. This is what I grab when we go for a night at the in-laws house or a roadtrip with our friends. I rarely bring this on a plane because it gets heavy to carry around on your shoulder!
I also love using my Transport Tote as my personal item on a plane. I have the zip-top version, which is clutch on a plane when you don't want all of the random things you've packed rolling all over the place. I like to alternate between reading / watching videos on my iPad mini and listening to podcasts or playing games on my phone, so I love having this little tech envelope inside of my purse so I can easily pull out all of my electronics (plus a credit card so I can buy myself a snack box ;) and leave my larger bag under the seat.
While I'm set on suitcases and totes, I'm on the hunt for some solutions for my toiletries, makeup and jewelry. The bags I use have been in rotation since I was in college and are basically falling apart. I've long admired the Truffle bags, they are such chic bags for easily getting through the TSA! I bought one for Jeff's sister last year and was so jealous when I saw it in person, I wanted to keep it for myself. But for Christmas my sister-in-law asked for a Dagne Dover bag, and having seen it in person I definitely am looking at ordering one. It has a couple mini mesh bags inside of it for keeping stuff organized, and the whole thing is waterproof and can be wiped clean.
Here are my picks for the best travel bags:
Truffle Clarity Case / Vera Bradley Weekender Bag / Delsey Carry-On Suitcase / Truffle Clarity Clutch / Madewell Zip-Top Transport Tote / Dagne Dover Toiletry Bag / Mark & Graham Travel Organizer
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