Brown Derby Shoes with Dress Shirt Chill Weather Outfits After 50

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Light Blue Dress Shirt Navy Floral Tie Grey Tweed Blazer Navy Overcoat Khaki Chinos Black Leather Holdall Brown Leather Derby Shoes

Marrying a dress shirt with khaki chinos is an on-point idea for a casually smart menswear style. Brown derby shoes are the simplest way to upgrade your ensemble. If you're not sure how to dress age-appropriately without giving up on style, this outfit is a surefire option.

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Clear Sunglasses White Dress Shirt White Pocket Square Grey Waistcoat Grey Check Blazer Beige Overcoat Beige Chinos Dark Brown Horizontal Striped Socks Dark Brown Leather Derby Shoes Dark Brown Leather Briefcase

Go for a straightforward but dapper choice marrying a dress shirt and beige chinos. And if you wish to easily level up this getup with one item, why not add a pair of brown derby shoes to the equation? This combination is a good illustration 50-something men can still very well slay in the style department.

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White Dress Shirt Dark Brown Pocket Square Dark Brown Suspenders Dark Brown Suit Navy Trenchcoat Navy Print Scarf Dark Brown Suede Derby Shoes

This sophisticated pairing of a dress shirt and a navy trenchcoat is really a statement-maker. A great pair of brown derby shoes ties this outfit together. And if we're talking fashion tips for mature gents, this look looks great on almost any guy.

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White and Red Vertical Striped Dress Shirt Grey Tie Dark Brown Leather Watch Dark Brown Leather Belt Camel Overcoat White Corduroy Dress Pants White Corduroy Blazer Dark Brown Leather Derby Shoes

Pairing a dress shirt and white corduroy dress pants is a surefire way to breathe refinement into your current outfit choices. Does this look feel too classic? Let a pair of brown derby shoes shake things up. This one is a stylish but also age-appropriate combo for a mature man.

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Dark Brown Sunglasses White and Blue Vertical Striped Dress Shirt Black Polka Dot Pocket Square Navy Polka Dot Scarf Black Overcoat Beige Dress Pants Black Socks Dark Brown Leather Derby Shoes Beige Double Breasted Blazer

A dress shirt looks especially classy when matched with beige dress pants. Feeling transgressive today? Switch up this look by wearing brown derby shoes. A perfect example for anyone who wonders how to dress as a mature guy.