I've had this Longchamp tote for years, and it still holds its place as one of my most used bags. The current version is called "Le Pliage Neo," which has a thicker, more structured nylon material than their standard tote, but is still wonderfully lightweight and folds flat. I'd recommend it for school, work, and everything in between when you need a durable bag that's fairly water-resistant and easy to clean. For travel, it's also good for protecting other designer bags while going through security and getting crammed under the seat. It fits my larger Prada tote in addition to my big makeup organizer!
When on the road, I have no problem with wearing an item on repeat, especially if it means traveling lighter. I usually pick a versatile piece or two to be the "workhorse," then plan a few outfits around it by tweaking something as simple as different shoes or denim color for different occasions. I originally got this sweater just as a basic, but surprised myself with how much I reach for it!
Here's a few outfit variations I've worn featuring this sweater, just in the past few weeks...
Comfy travel (shown below): with stretchy leggings + block-heeled booties
Skirted: tucked into an A-line skirt, with weatherproof flat boots
Preppy casual: worn under a puffer vest, with gray jeans (not pictured) + cozy gear
Layered up: Under a puffer coat + shrunken fit moto jacket with skinny jeans
Fit-wise, an XS regular in this sweater is a slouchy casual fit on me. For someone my size I'd recommend xxs which looks like it just came back in stock! Also, note it's 100% cotton so shrinks down a little bit after a machine wash & dry. You might need to re-shape the mock neck a bit with an iron after drying.
I also wanted to mention this wool hat (comes in classic black, too), which runs very small in the inner circumference area! The negative reviews are mostly all about the smaller fit. If you can never find hats that fit narrow enough, definitely give this one a try in size S/M. It has a beautiful shape and flops at just the right places without being overwhelming.