I picked up this Proenza Schouler PS1 in Military about a year ago -- while I don't use it everyday, it's one of my favourite all-rounders: deceptively roomy, light to carry, and goes with everything.
This is the medium size, measuring 13" x 9" x 4", is just large enough for me to bring everything I need without giving me too much room to fit in the kitchen sink. I used to be obsessed with the oversized bucket bags of the mid-to-late 00's, but I'm starting to embrace a more streamlined (ish) approach.
This bag can be carried in hand and worn cross-body, but fair warning: the strap is not quite long enough to be a traditionally slouchy messenger bag. You'll see in the video that the 16" drop sits very high on me, especially with my freakishly long torso, but I almost prefer it because it reminds me of those one-strap backpacks in grade school.
I feel like I should have treated this bag with some sort of leather care, but I have no idea what products are safe to use on this leather. Got advice? Leave it below!
The bag closure is a flip-lock closure, with two additional straps to keep the envelope flap down; for a more casual look (read: when I'm in a hurry and can't give a bleep), I'll keep the straps loose, but the straps do give the bag more detail.