I admittedly have a bit of a thing against traditional bootcut or flared jeans. It has something to do with the lack of sleekness (extra fabric flapping around the ankle and shoe) and some old notion that they aren't current. I know this is wrong, and I need help adjusting my eye. All I wear are skinnies and cropped flares, and I feel a little out of touch . I have 1 or 2 pair of bootcuts that fit and that I'm willing to wear ...the question is, how?

What is the most up-to-date way to style them? Caveats:
1. I am not in great shape and carry a lot of weight in my midsection . This may be tmi, but I look about 5 months pregnant at the best of times.

2.Tucking in is beyond my scope of imagination, thus my reliance on the long-over-lean formula of skinnies and a long top or jacket.

3. My legs are decent, and proportion is not an issue.

4. I don't love button-up shirts - they never fit properly , and can look too masculine on me.

So all of these barricades aside, tell me how to style them, with what jacket or top, and with what footwear - please! I want fashion forward looks, nothing too staid, unless it involves a Gucci belt and a Smythe jacket (my fantasy look but way out of reach now). Heck,even Accidental Icon posted a pic of herself wearing a pair today!