I'll admit that I sat out the boyfriend jean trend while pregnant and post-partum because I felt schlumpy enough without adding extra bagginess. So I'm a total novice to the boyfriend jean look and I have no idea what I'm doing. But it seems like an ideal MOTG formula so I'm giving it a go. Any advice or suggestions would be much appreciated!

I've tried buying several pair online and they all looked ridiculous on me (massively baggy, ballooning at the hip) and I sent them all back. Maybe it's because I'm an IT?
I pulled out these stretched out old skinnies that I already owned and rolled them up. They still seem a bit tight. But are they baggy enough to work for experimenting with the "boyfriend jean" look?

And finally, how do you transition this look to fall?

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