Red Briefcase Warm Weather Outfits After 50

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Light Blue Sunglasses Multi colored Bracelet White Crew-neck T-shirt Burgundy Leather Briefcase Navy Sweater Vest White Chinos Navy Canvas Desert Boots

A navy sweater vest and a red briefcase are a good go-to combo to keep in your casual closet. You know how to play it up: navy canvas desert boots. No doubt, a foolproof option if we're talking dressing ideas for older guys.

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Black Sunglasses White Dress Shirt White Pocket Square Charcoal Tie Grey Suit Burgundy Leather Briefcase Black Leather Brogues

A grey suit and a red briefcase are the kind of a winning off-duty outfit that you so desperately need when you have no time. Tap into some David Beckham stylishness and add a pair of black leather brogues to the mix. Those who wonder how to dress with style in your 50s, you have your answer.

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Navy Sunglasses Burgundy Leather Briefcase Silver Leather Watch White Polo White Chinos Brown Suede Desert Boots

Stylish yet practical, this look features a white polo and a red briefcase. Turn up the classiness of this look a bit by finishing off with brown suede desert boots. Think you can't pull off cool casual outfits as you reach your 50s? This pairing is hard proof of otherwise.