Playing with cropped (flared?) jeans trend

Ever since Angie started to post about the cropped jeans trend I was intrigued. I have already mastered the cropped skinnies in summer but honestly fall / winter version of cropped jeans left me baffled.
I was not sure if I want to buy any as I was not sure I will really wear them so idea of chopping the existing pair sounded good. There was only one problem – to find the existing pair which can be chopped. I do not have that many jeans to start with in the first place. There are 2 pairs of BFs which are the wrong silhouette for this trend. There are 2 pairs of bootcuts and 2 pairs of full length skinnies which I cannot bring myself to chop at all because it was such an ordeal to find them long enough in the first place (tall gals will understand).
The only possible candidate was Gap faded bootcuts which I turned into straight legs last year. Somehow I found that I was not wearing them as much as others in this shape and at full length so I went scissors- happy on them!
Here is where the bafflement began. I am restricted by the footwear I can wear in winter: I have only one pair of  flat Chelsea booties which are winter-worthy. Fortunately they are tall enough in the shaft to possibly work with the cropped trend. Unfortunately they are BLACK which is hard to pair with cropped LIGHT BLUE jeans - and FLAT which makes them more leg shortening for this trend!
However I tried. Here are my attempts from this month. In both cases the tops are ink blue - I wanted to bookend the black booties here so they are not too disconnected with the light jeans. Pics 1-3 are with high-low relaxed fit t-neck and knee-high socks to get some skin showing. I have included back and side shots so you can see how the hems look from all angles.
Pics 4-6 are with black socks (too cold for nylons), shorter sweater and a moto jacket. I have also added a shot with a long coat I wore over the whole thing.
I am just not sure if it looks ridiculous on me or not. When I look down on my feet in these jeans I find the look very funny – like I am wearing too short jeans here – but nobody looks at me at this angle but myself. Is the contrast between the light jeans and black boots too jarring? I am half-tempted to try Angie’s picks from Gap and BR but another part of me holds me back…
What do you think? Any suggestions for improvements? Also – is the length right or should I let the hems down a bit so they cover the tops of the booties completely? Or is this particular pair is a disaster and I should get a real cropped version to try before I decide if this trend is for me or not?

 Please help this cropped jeans challenged lady! 


Go to the full post to see all of the pictures →