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Shop a fashion editor's picks, from Steve Madden to Prada.14-day returnsVideosYou will see more English now.6:50How to Wear Jeans with Ankle Boots | 15 Cute Boot Outfits!YouTube · Marlene | Life with Mar6 minutes, 50 secondsOct 25, 20213 key moments in this video11:06How to Wear Boots With The Hottest Jean Trends of 2022/2023YouTube · Busbee Style11 minutes, 6 secondsFeb 16, 20227 key moments in this video7:06How to wear BOOTS with JEANS | TutorialYouTube · Emily Elizabeth May7 minutes, 6 secondsSep 9, 20207 key moments in this videoFeedbackView all Steven By Steve Madden Darla Sock Booties, How To Wear Ankle Boots With Jeans. For a classic casual look, combine a pair of slim black jeans with black boots. Look for jeans with a taper down to the ankle, which should sit just on the top . Steven Madden Wallet, The Ultimate Guide to Styling Black Jeans with Brown Boots. 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