Yellow Leather Briefcase Smart Casual Fall Outfits After 40

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Dark Brown Wool Hat Light Blue Plaid Dress Shirt Olive V-neck Sweater Blue Blazer Pink Bracelet Blue Plaid Scarf Black Leather Watch Orange Leather Briefcase Grey Skinny Jeans Beige Suede Desert Boots

This pairing of a blue blazer and a yellow leather briefcase is on the off-duty side but is also seriously stylish and incredibly dapper. Let's make a bit more effort with footwear and introduce a pair of beige suede desert boots to this look. Rest assured, this getup will keep you toasty as well as looking stylish in this transitional weather. If you're wondering how you should dress as a middle-aged gentleman, this ensemble gives a good idea.