Brown Derby Shoes with Dress Shirt Dressy Fall Outfits

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Black Sunglasses White and Black Vertical Striped Dress Shirt Black Print Tie Brown Overcoat Tan Double Breasted Blazer Khaki Dress Pants Black Socks Dark Brown Leather Derby Shoes

Swing into something smart yet modern with a dress shirt and khaki dress pants. Add brown derby shoes to easily ramp up the wow factor of this ensemble. As you can see here, it's super easy to look stylish and stay comfortable when cooler weather hits, all thanks to combinations like this.

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Brown Wool Hat Black Sunglasses Yellow Dress Shirt Dark Brown Polka Dot Tie Brown Wool Three Piece Suit Olive Overcoat Black Socks Dark Brown Suede Derby Shoes

Reach for a dress shirt and an olive overcoat and you're guaranteed to make women swoon. If not sure as to the footwear, complete this outfit with a pair of brown derby shoes. If it's one of those bleak autumn days, what better to cheer it up than a seriously stylish look like this one?

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Black Dress Shirt Black Print Pocket Square Brown Wool Blazer Silver Watch Black Dress Pants Olive Polka Dot Socks Dark Brown Leather Derby Shoes

Go for something elegant yet trendy in a dress shirt and black dress pants. Introduce brown derby shoes to the mix to instantly dial up the street cred of your look. Seeing as temperatures are dropping, this ensemble is a good idea for the transitional season.

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Grey Dress Shirt Grey Tie Black Waistcoat Black Sunglasses Charcoal Blazer Black Dress Pants Dark Brown Leather Derby Shoes

This refined combo of a dress shirt and black dress pants is truly a statement-maker. You could perhaps get a little creative on the shoe front and tone down your ensemble by rounding off with a pair of brown derby shoes. When it comes to dressing for transitional weather, nothing beats a knockout ensemble that transitions easily between seasons.

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Purple Gingham Dress Shirt Dark Purple Tie Charcoal Wool Dress Pants Dark Brown Leather Derby Shoes Grey Cardigan

This elegant combination of a dress shirt and charcoal wool dress pants is a popular choice among the trendsetting chaps. Brown derby shoes are the simplest way to infuse a hint of stylish effortlessness into your getup. You can rest assured this combo is ideal for fluctuating fall weather.