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Classic Fit Deck Pant by Nautica, $32.50 While jeans might not fly for many office dress codes, the right pair of deck pants can feel just as comfortable and not raise any eyebrows

Notes It has the ability to truly enliven any dish

Bonus: That smocking in the back for an adjustable fit

In fall or winter, opt for satin or heavier fabrics, and consider layering with a matching wrap or bolero for warmth without compromising style

Perhaps one of the most enduring images of everyday fashion in the fifties is the poodle skirt. Credited to Juli Lynne Charlot from California, these simple felt skirts were cut in a circle and could have any sort of embellishment, not just a poodle (Milford-Cottam 20)