Sometimes, you have to put on a pair of (admittedly, cheap large store) so-so fitting khaki pants and feel a bit frumpish and clunky and all the like, to realize that you need to focus on what fits well, flatters, and feels good on. So:
Order that dress. It's cool, it should be a good fit, and you know you'll feel good wearing it.
Pay attention to instinct and plan to pick up a pair of grey leggings. The ones from the big red store have worked out just fine.
Listen to fit feedback on the boots and INVEST (capital letters because it will be a significant outlay of cash) in a pair that are the fetch the gold ring from the mountain fitting pair.
Because you feel good in dresses and your guy likes how you look in dresses. Win-win, chick.
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