Blue Jeans with Brown Leather Work Boots Smart Casual Chill Weather Outfits For Men After 50

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Navy Beanie Navy Sunglasses Black Turtleneck Black Overcoat Black Leather Gloves Blue Jeans Brown Leather Work Boots

For an outfit that's street-style-worthy and casually sleek, wear a black overcoat and blue jeans. Add brown leather work boots to your outfit to keep the outfit fresh. The ability to wear combinations like this is one of the dividends of reaching middle age.

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Black Beanie Light Blue Chambray Long Sleeve Shirt Navy Horizontal Striped Sweater Vest Charcoal Wool Blazer Dark Brown Leather Belt Navy Jeans Brown Leather Work Boots

For something on the classic and casual end, consider this combo of a charcoal wool blazer and blue jeans. Avoid looking overdressed by rounding off with brown leather work boots. So if you're looking for a good-looking and age-appropriate combination, you found it.