White and Red Dress Shirt with Tassel Loafers Dressy Chill Weather Outfits After 40

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Black Wool Hat Teal Pocket Square Black Tie Dark Green Plaid Blazer White Dress Shirt Black Overcoat Dark Green Plaid Dress Pants Black Socks Black Leather Tassel Loafers

Go for classy style with a white and red dress shirt and dark green plaid dress pants. If in doubt about what to wear when it comes to shoes, stick to tassel loafers. This is a modern and age-appropriate outfit for over-40 gentlemen.