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If you do prefer a wider pant leg, go for a cropped look with your dressy flats, and keep in mind a pointy toe flat is always more flattering than a rounder toe

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tank top + linen shorts + ballet flats + straw bag + accessories top | shorts | bag | shoes | bracelet | earrings Bring out your white tank top during the hot days spent strolling around street markets and eating at a delicious traditional Italian restaurant

In that case I could wear either, black would be a little smarter, a little more modern, but both work well See the article on Friday maybe to get a sense of what I mean, comparing that to the outfit I linked to Hi Simon, I came back to this article after reading your piece on commissioning a cap toe oxford from Kohei, and it got me thinking