Dark Brown Ankle Boots with Dress Shirt Chill Weather Outfits In Their 20s

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Yellow Knit Scarf Grey Duffle Coat Light Blue Dress Shirt Beige Leather Belt Navy Jeans Dark Brown Suede Ankle Boots

This combo of a dress shirt and navy jeans combines comfort and utility and helps you keep it clean yet contemporary. Our favorite of a countless number of ways to round off this outfit is with dark brown ankle boots.

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Black Sunglasses Beige Cowl-neck Sweater White Dress Shirt Beige Coat Orange Leather Clutch Beige Culottes Brown Leather Ankle Boots

This off-duty combo of a dress shirt and beige culottes is very easy to pull together in no time, helping you look cute and prepared for anything without spending too much time rummaging through your wardrobe. If you want to break out of the mold a little, complement this getup with dark brown ankle boots.

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Red Beanie Red Turtleneck Multi colored Plaid Dress Shirt Olive Parka Blue Jeans Brown Leather Ankle Boots

This combination of a dress shirt and blue jeans is hard proof that a pared down off-duty ensemble doesn't have to be boring. If not sure as to the footwear, stick to dark brown ankle boots.