I wear this type of look a lot. It is an easy uniform for me. The right length blazer (i like the length in this picture above--with leggings it has to cover the bum) and good leggings are the key. The leggings have to be thick and look more like pants than exercise gear.I quite like the look of leggings + oversize men´s shirt with bold but simple jewelry.
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Just an example of the current trendy look. Masculine oversize items to contrast with leggings.
It's easy to swap out black or dark skinny jeans with this look. Also can wear docs, boots like this, or block heel boots for some length.