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You look cute in them, but the shorts/boots look reminds me of vintage flight attendant. I guess it all depends on what sort of image you're trying to project.
I think they'd work much better in a different styling - top tucked in (belt or no belt, up to you) and low boots (chelsea boots or oxfords or something like that, not higher than ankle booties). For me, this is the only way they can look good, sorry. Otherwise not a huge fan of winter shorts either.
HUGE yay for you. I think this silhouette looks fab on slim rectangles and ITs (woohoo!) because winter shorts draws my attention right to the slim hips.
I like this particular outfit as-is (lovely textures) but don't love it. The like-but-not-love is mostly a color problem, to my eye. May I ask whether the shorts are tweeded with a warm white (eg, cream) or a cool white (eg, pure white)? I ask because the cream sweater's tone is too-close-to-contrast but too-warm-to-match the shorts.
