Dress Shirt with Ankle Boots Dressy Cold Weather Outfits

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White and Blue Gingham Dress Shirt Black Coat Burgundy Scarf Charcoal Wide Leg Pants Burgundy Velvet Ankle Boots

Rock a dress shirt with charcoal wide leg pants to pull together a stylish and put together outfit. Complete your outfit with ankle boots and ta-da: this look is complete.

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Red and Black Check Dress Shirt Red Coat Black Print Leather Clutch Black Skinny Pants Black Leather Ankle Boots

For an outfit that's nothing less than steal-worthy, dress in a dress shirt and black skinny pants. Our favorite of an infinite number of ways to finish this look is with ankle boots.

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Gold Earrings Black Turtleneck White Dress Shirt Black Leather Belt Blue Jeans Burgundy Leather Ankle Boots Olive Coat

This pairing of a dress shirt and blue jeans is proof that a safe off-duty ensemble can still look chic. If in doubt about the footwear, stick to a pair of ankle boots.

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Red Coat Black Wool Tights Black Suede Ankle Boots Gold Bracelet Black Embellished Sheath Dress Red and Black Plaid Dress Shirt

This pairing of a dress shirt and a red coat lies somewhere between elegant and relaxed. Introduce ankle boots to your ensemble for maximum effect.

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White Dress Shirt Silver Necklace Silver Clutch Grey Plaid Dress Pants Beige Cutout Leather Ankle Boots Pink Polka Dot Coat

This pairing of a dress shirt and grey plaid dress pants is extremely easy to pull together in seconds time, helping you look amazing and prepared for anything without spending a ton of time combing through your closet. On the footwear front, this outfit is rounded off wonderfully with ankle boots.