Red and Black Chinos Smart Casual Fall Outfits After 50

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Clear Sunglasses White Dress Shirt Olive Pocket Square Dark Green Check Blazer Mint Sweater Vest Dark Brown Leather Watch Burgundy Chinos Light Blue Socks Dark Brown Leather Desert Boots

This combo of a dark green check blazer and red and black chinos is definitive proof that a simple ensemble doesn't have to be boring. Complement your ensemble with dark brown leather desert boots and ta-da: the outfit is complete. This ensemble is a really nice idea, especially for autumn, when the temps are getting lower. This outfit demonstrates that dressing well as you move into your 50s is totally doable.

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Beige Beanie Clear Sunglasses Beige Polo Neck Sweater Grey Leather Watch Burgundy Plaid Chinos Dark Brown Suede Double Monks

For an outfit that's pared-down but can be dressed up or down in a great deal of different ways, consider teaming a beige polo neck sweater with red and black chinos. Opt for a pair of dark brown suede double monks for an element of elegance. You can bet this outfit is the answer to all of your transeasonal wear problems. When it comes to fashion for over-50 guys, this getup looks great on most.

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Black Beanie Clear Sunglasses Black Turtleneck Grey Check Pocket Square Tan Blazer Charcoal Overcoat Burgundy Plaid Chinos Black Leather Tassel Loafers

This combo of a charcoal overcoat and red and black chinos is a foolproof option when you need to look stylish in a flash. Finish off with a pair of black leather tassel loafers to transform this getup. This one is a great choice if you're crafting a standout outfit for summer-to-fall weather. Classic getups like this are worth having in your wardrobe at any age.

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Charcoal Beanie Clear Sunglasses Black Leather Long Sleeve Shirt Tan Knit Wool Turtleneck Charcoal Leather Watch Burgundy Plaid Chinos Navy Velvet Loafers

A tan knit wool turtleneck looks especially cool when paired with red and black chinos in a relaxed casual look. Go off the beaten track and change up your outfit by rounding off with a pair of navy velvet loafers. As you can see here, it's very easy to look amazing and stay toasty come cooler weather, all thanks to looks like this. If you frequently wonder how to dress appropriately for your age without giving up on fashion, this pairing is a wonderful example.

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White and Red Check Dress Shirt Pink Tie Grey V-neck Sweater Beige Trenchcoat Burgundy Chinos Brown Leather Derby Shoes

A beige trenchcoat and red and black chinos are indispensable players in any man's sartorial collection. On the fence about how to finish off this look? Finish off with a pair of brown leather derby shoes to ramp up the wow factor. This combo is a viable option if you're putting together a well-coordinated ensemble for transeasonal weather. This combination illustrates that as a middle-aged man, you still have a wide range of outfit options.