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Think oversized legwear, surreal prints, and materials that shimmer, shift, or baffle the eye

Late 1950s Bride with Bridesmaids and Full Wedding Group 1958 Outfits of Female Guests at Barbara's Wedding 1958 The two images left are especially interesting from a fashion history point of view

It all comes down to knowing your style, what occasion you'll dress for, and even considering whether the venue suits your look

For her engagement, the So High School singer seemed to wear the dress only with strappy sandals and her gold, diamond-studded, Cartier watch, which she wore on Kelces New Heights podcast earlier this month to announce her new studio album, The Life of a Showgirl