Star--that seems to work for a lot of people, wearing under jackets. I just wonder what happens when we need to take off the jacket?

Ket--you sell the crossbody so well! Such specific examples. In addition to the bags you mentioned, do you remember the messenger bag craze from the late 90s/early aughts? That's all I wore. That would be a good look again.

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I have to say I’ve been wearing messenger bags and other crossbody styles since the 90s trend; I am not a small person and am currently bustier in proportion than what I am used to. It has happened in my lifetime that I’ve tried on a bag and immediately rejected it due to the way it cut between my breasts, but rarely. Many more cross body styles of different strap types have worked just fine.

oh!! I do remember the 90s messenger bag craze! I feel it even bled as late into the 2010s?? I remember people where I lived, particularly young to middle-aged men, still wearing crossbody messenger bags through 2015 or so. Further, I remember Joseph Gordon-Levitt wearing one almost exclusively in 500 Days of Summer.


I think it's an excellent look. With the 90s making a strong sartorial comeback, it's time to bring it back, I feel!

Curious and excited to see if you embrace a messenger bag.


Jules--sounds like straps are important!
Ket--not sure if I will embrace this trend, but it sure does look cool on others.