169 Smart Casual Chill Weather Outfits For Men After 50

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Black Sunglasses White Dress Shirt Brown Plaid Waistcoat Brown Leather Biker Jacket Dark Brown Leather Belt Beige Jeans

This combination of a brown leather biker jacket and beige jeans looks awesome and instantly makes any gent look stylish. This ensemble shows that dressing well well into your 50s is not particularly hard.

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Black Sunglasses White Knit Turtleneck White Pocket Square Grey Overcoat Black Suede Gloves

This combination of a grey overcoat and a white knit turtleneck speaks manly elegance and class. This look is probably what you're looking for as an older gentleman.

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Beige Wool Hat Dark Brown Sunglasses Burgundy Turtleneck Dark Brown Overcoat Navy Skinny Jeans Dark Brown Leather Chelsea Boots

Wear a dark brown overcoat and navy skinny jeans to prove you've got serious sartorial prowess. Dark brown leather chelsea boots are guaranteed to inject a hint of elegance into your look. No doubt, a fail-safe option when it comes to style tips for mature gents.

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Black Sunglasses Black and White Bandana Beige Crew-neck Sweater Navy Denim Jacket Black Overcoat Olive Dress Pants Black Leather Derby Shoes

Dress in a black overcoat and olive dress pants to look like a true fashion maven. Dial up the wow factor of your getup by rounding off with a pair of black leather derby shoes. Just because you're in your 50s, doesn't mean you can't dress fashionably, and this combination demonstrates exactly that.

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Dark Brown Tie Beige Cable Sweater White Dress Shirt Olive Quilted Gilet Dark Green Wool Blazer Dark Brown Chinos Dark Brown Leather Casual Boots

Pair an olive quilted gilet with dark brown chinos if you wish to look casually stylish without too much work. Step up your ensemble with dark brown leather casual boots. And if we're talking fashion at 50 plus, this combo is ideal.