Blue Dress Pants with Chelsea Boots Fall Outfits For Men After 50

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White Dress Shirt Black and White Horizontal Striped Tie White Pocket Square Black Overcoat Black Double Breasted Blazer Dark Brown Leather Briefcase Blue Wool Dress Pants Dark Brown Suede Chelsea Boots

This combination of a black overcoat and blue dress pants comes in useful when you need to look sophisticated and extra stylish. Want to break out of the mold? Then why not introduce chelsea boots to the mix? When it's one of those gloomy fall days, sometimes only a kick-ass look like this one can cheer it up. Just because you've passed the big five-oh, doesn't mean you can't look fashionable, and this getup demonstrates exactly that.

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Black Turtleneck Black Quilted Barn Jacket Navy and Green Plaid Dress Pants Black Leather Chelsea Boots

For an ensemble that's worthy of a modern fashion-savvy guy and effortlessly classic, choose a black quilted barn jacket and blue dress pants. Our favorite of a ton of ways to finish this look is a pair of chelsea boots. On not-so-bone-chilling days, you can wear this transitional ensemble and look absolutely amazing. Outfits like this help accept this next milestone that is your 50s with dignity and confidence.

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Navy Pea Coat Black Sunglasses Black Leather Gloves Navy Wool Dress Pants Black Leather Chelsea Boots

Go all out in a navy pea coat and blue dress pants. To add a dash of stylish nonchalance to this ensemble, add a pair of chelsea boots to the equation. On not so cold afternoons, work this easy-to-transition look and look absolutely amazing. Dressing inspo like this will help you stay incredibly fashionable even well into your 50s.