I had a doctor's appointment today and on the way back, I decided to take the metro to the mall. I stopped by at Gap to try the Sexy Boyfriend jeans and I have to say, I'm a little confused about what these are supposed to fit like.

I first tried my regular size (see pic 1 to 3). The waist fit pretty well and these are definitely slouchier than any other jeans I have ever worn. But are they slouchy enough?

Pics 4 and 5 show one size up. These are so loose in the waist that they sit on my hip and even then, I was petrified that they would fall off! I can take these off without unbuttoning. Is this the right amount of slouch? If I get this size, should I get the waist altered?

I'm also wondering if boyfriend jeans need to be worn with a pair of heels (however low) or if I can make them work with flats? I'm picturing my oxfords with these and I like the idea of that menswear-ish vibe.

Thanks for helping!

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