Ankle Boots with Dress Shirt Dressy Cold Weather Outfits In Their 20s

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

Flex your styling chops by pairing a dress shirt and grey plaid dress pants. Add ankle boots to the equation et voila, the ensemble is complete.

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Olive Print Scarf Light Blue Dress Shirt Brown Coat Blue Skinny Jeans Black Leather Satchel Bag Black Leather Ankle Boots

Chic yet comfy, this getup combines a dress shirt and blue skinny jeans. Add a pair of ankle boots to this ensemble and off you go looking spectacular.

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Black Dress Shirt Silver Necklace Grey Check Coat Black Floral Skinny Pants Silver Leather Ankle Boots

Try teaming a dress shirt with black floral skinny pants for glamour with a modern take. If you're hesitant about how to round off, a pair of ankle boots is a nice idea.

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Black Polka Dot Bandana Red and White Polka Dot Dress Shirt Grey Check Coat Blue Jeans Black Leather Tote Bag Black Leather Ankle Boots Black Sunglasses

This outfit with a dress shirt and blue jeans isn't so hard to score and easy to change. Complement this outfit with a pair of ankle boots and the whole look will come together.