Briefcase Casual Fall Outfits After 50

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Clear Sunglasses Navy V-neck Sweater Navy and White Gingham Short Sleeve Shirt Navy Jeans Navy Leather Casual Boots Dark Brown Leather Briefcase

This combination of a navy v-neck sweater and a briefcase is uber stylish and provides instant cool. To introduce some extra depth to this ensemble, rock a pair of navy leather casual boots. As you can see, this outfit is a really nice pick, especially for transitional weather, when the temps are getting lower. If you're often not sure how to dress appropriately for your age, this outfit is a practical example.

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Clear Sunglasses Grey Vertical Striped Short Sleeve Shirt Dark Brown Shirt Jacket Khaki Chinos Grey Canvas Briefcase Charcoal Canvas Low Top Sneakers

A dark brown shirt jacket and a briefcase are absolute menswear staples that will integrate nicely within your daily casual routine. Get a bit experimental in the footwear department and complete your look with charcoal canvas low top sneakers. Can you see how extremely easy it is to look dapper and stay comfortable come colder days, all thanks to combos like this? This combo illustrates that even in your fifties you still have a wide array of dressing options.

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Clear Sunglasses Grey Crew-neck T-shirt Light Blue Short Sleeve Shirt Brown Blazer Brown Leather Belt Navy Jeans Olive Canvas Briefcase Grey Canvas Low Top Sneakers

If you're looking for an off-duty yet stylish look, try pairing a brown blazer with a briefcase. Tap into some Idris Elba stylishness and complement this getup with grey canvas low top sneakers. Seeing as temps are dipping, this ensemble appears a smart option for in between seasons. This outfit is a huge inspiration to anyone who was cautious about wearing casual outfits as a 50-year-old gentleman.

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Charcoal Baseball Cap Clear Sunglasses Red Paisley Bandana White Crew-neck T-shirt Olive Long Sleeve Shirt Camel Plaid Overcoat Blue Jeans Olive Canvas Briefcase Grey Canvas Low Top Sneakers

Opt for a camel plaid overcoat and a briefcase for relaxed dressing with a contemporary spin. Want to go all out on the shoe front? Add a pair of grey canvas low top sneakers to the mix. When temps are getting lower and fall is settling in, you'll love this combination as your uniform for in-between weather. Think over-50 gents can't pull off modern off-duty dressing? This combo will prove you otherwise.

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Dark Brown Sunglasses Dark Green Floral Scarf Grey Quilted Gilet Silver Watch Brown Knit Wool Blazer White and Blue Vertical Striped Long Sleeve Shirt Olive Canvas Briefcase Grey Cargo Pants Navy Suede Desert Boots

A grey quilted gilet and a briefcase have become a favorite casual pairing for many stylish guys. Complete this outfit with navy suede desert boots to make the outfit slightly sleeker. This outfit is an excellent pick when it comes to an easy-to-transition ensemble. Wondering how to perfect casual looks as you head into your 50s? This pairing is a wonderful example.