Brown Ankle Boots with Dress Shirt Fall Outfits In Their 20s

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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 combo of a dress shirt and beige culottes delivers comfort and casual cool. Hesitant about how to finish? Add brown ankle boots to the equation to amp up the chic factor. As you can see here, it's extremely easy to look on-trend and stay toasty when cooler weather hits, thanks to this getup.

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Multi colored Plaid Dress Shirt Tan Sunglasses Dark Brown Leather Watch Orange Leather Tote Bag Navy Skinny Jeans Tobacco Leather Ankle Boots

Pair a dress shirt with navy skinny jeans for a casual ensemble with a twist. This ensemble is complemented wonderfully with a pair of brown ankle boots. As you can see, this ensemble is a really smart idea, especially for summer-to-fall weather, when the temperature is starting to drop.

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Charcoal Dress Shirt Black Suede Button Skirt Dark Brown Suede Ankle Boots

This relaxed pairing of a dress shirt and a black suede button skirt comes to rescue when you need to look chic in a flash. Throw a pair of brown ankle boots in the mix and the whole look will come together perfectly. There's no better way to spice up a bleak autumn day than a cool outfit like this one.

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Dark Brown Suede Lace-up Ankle Boots Blue Ripped Skinny Jeans Beige Blazer White Crew-neck T-shirt Black and White Gingham Dress Shirt Black Sunglasses

You can look totaly chic without trying too hard by wearing a dress shirt and blue ripped skinny jeans. Up this whole look by finishing off with brown ankle boots. When temps are dipping and fall is in the air, you'll love this look as your go-to for in-between weather.