100 Fall Outfits For Men After 50

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Red Beanie Blue Chambray Long Sleeve Shirt Dark Brown Wool Shirt Jacket Silver Bracelet Brown Corduroy Chinos Brown Leather Work Boots

This smart casual pairing of a dark brown wool shirt jacket and brown corduroy chinos is super easy to throw together in next to no time, helping you look dapper and ready for anything without spending a ton of time searching through your closet. If you wish to effortlessly play down your outfit with one piece, round off with a pair of brown leather work boots. This combination is an appealing choice if you're figuring out a cool look that will take you from summer to fall. If you frequently wonder how to dress your age while looking stylish, this outfit is a practical illustration.

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Mustard Beanie Mustard Knit Turtleneck Navy Jeans Silver Bracelet Mustard Athletic Shoes

If you're hunting for a relaxed casual and at the same time on-trend look, dress in a mustard knit turtleneck and navy jeans. Add a pair of mustard athletic shoes to the equation to inject a sense of stylish nonchalance into this look. Seeing as temps are dipping, this getup appears a savvy pick for the season. This pairing is a big inspo to anyone who had doubts about wearing casual clothing in your 50s.

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Black Beanie Dark Brown Sunglasses Brown Gingham Long Sleeve Shirt Brown Cargo Pants Dark Brown Leather Casual Boots

This casual combo of a brown gingham long sleeve shirt and brown cargo pants can take on different nuances according to the way it's styled. Serve a little mix-and-match magic by sporting a pair of dark brown leather casual boots. So when summer is over and fall is taking its place, you may find this look your uniform. This getup should inspire anyone who wasn't sure about wearing casual clothing after fifty.

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Black Beanie Dark Brown Sunglasses Orange Cardigan Silver Watch Black Leather Belt Charcoal Jeans Black Leather Work Boots

An orange cardigan and charcoal jeans will convey this neat and relaxed vibe. For something more on the cool and casual side to finish your look, introduce black leather work boots to this getup. Seeing as fall is in the air, this ensemble is a good idea for the season. This outfit shows how to keep succeeding in casual dressing as an over-50 gentleman.

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Orange Beanie Dark Brown Sunglasses Orange Sweatshirt Navy Pea Coat Blue Jeans Olive Print Canvas Tote Bag White and Green Canvas Low Top Sneakers

Consider pairing a navy pea coat with blue jeans if you seek to look stylish without putting in too much effort. Throw in a pair of white and green canvas low top sneakers to instantly turn up the style factor of this look. It's a viable choice when it comes to planning a kick-ass look for weird transition weather. This combination proves that staying fashionable as you head into your 50s is easier than one might think.