Floral Cheesiness

With my first purchase of winter cropped pants ever, I am now a full convert to the wool shorts trend. I am so in love with this pair that I had to wear them again soon and try them with tights (and I am on the scout for more more more). I wanted to do booties and a blazer, but it is nowhere near that kind of cold yet in GA, so I thought this flippy cardigan would be a nice pairing.

The BF didn't say anything this morning but did present me with the raised eyebrow, which usually signifies the silent "I love you, but I question your attire, so I am not going to say anything at all because I don't want you to kick my butt." I don't know, is this look a little too "young?"

Top: J. Crew silk brulee tank (similar online here)
Sweater: Forever 21 peplum country (worn here and here before)
Shorts: Forever 21 wool blend (worn here before)
Tights: Anne Klein
Shoes: Franco Sarto (similar online here)

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Here's a case of "you looked way better online" - take these leather plimsolls from Boden and how those gazelle-leggy models are able to look so sporty-chic in them with only their bottom halves showing:

And here's reality of the leather plimsolls (and these pics do nothing to convey the Chester-the-Cheetah-ness of these big pancake-wide shoes with the weirdly tan color rubber toe caps). And no, I didn't bother tying them - partly because I tried with one and you can't really use the laces to pull the shoe together:

I guess I should stick to my rubber-soled ballet flats for casual footwear for now - or even my Skechers. Do you have any recs for finding good casual / sporty footwear?