Claire Leather Double-Gusset Tote, $250, available at Italic
How much it should cost: $785-$1,250
Made by the same manufacturer as: Prada and Miumiu
Our review: I was pleasantly surprised by how much I've used and loved this bag since it appeared on my desk a couple months ago. It's deceptively spacious inside, which makes it great for carrying to work, and I love that it has multiple handle options so I can swing it over my shoulder if I need a free hand.
The interior has two large, open pockets on each side with a zippered divider pocket in the middle. I can easily fit my 13-inch laptop, charger, and daily essentials in one side, along with a pair of flats, my lunch, and a small umbrella in the other. Honestly, I kind of feel like Mary Poppins when I carry it!
I got it in the dusty blue color (the picture above shows it to be a little darker than it really is), which looks relatively neutral even when paired with colorful outfits, but it also comes in black for a more basic option. —Sally Kaplan, Insider Picks editor