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Spears and Timberlake, who dated from 1999 to 2002, turned quite a few heads when they stepped on the red carpet in matching looks, with the *NSYNC star, now 42, rocking a Canadian tuxedo (and even a denim hat) while the Toxic singer, now 41, sported a strapless Kurt and Bart denim evening gown with a coordinating purse
Semi-formal shoes Block heels, dressy flats, wedges, low heeled sandals, slingbacks, and polished sandals, especially for outdoor or daytime weddings
Pamela $139 Black A-Line V-Neck Pleated Chiffon Dress 4.2 (196) +70 Click to save this to your favorites
Adding sneaker-like comfort without making a dress shoe look too much like a sneaker has been the biggest challenge for comfortable dress shoes in the past, and we think Cole Haan nailed it here
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