“Pairing white denim with a white button-up in winter just doesn’t work,” she says.. “But rather, a monochromatic winter look comprised of a cream satin maxi skirt, oversized cream knit, and matching cream knee high boots looks extra polished and chic in the winter months.”
Gregory’s hack for transitioning a summer look to something more autumnal? Add one seasonal piece to your look.
Below are five of Gregory’s must-have summer-to-fall staples plus her expert tips on how to style them.

