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

Favorite

Unfavorite

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

If it's comfort and functionality that you're seeking in an outfit, reach for a dress shirt and blue skinny jeans. Add black ankle boots to the equation and the whole look will come together.

Favorite

Unfavorite

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

For an off-duty outfit, choose a dress shirt and blue jeans — these items fit pretty good together. Black ankle boots work wonderfully well here.