White and Red Vertical Striped Dress Shirt with Grey Suit Dressy Fall Outfits After 40

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White Vertical Striped Dress Shirt Grey Tie Beige Fur Collar Coat Grey Suit Navy Socks Burgundy Leather Oxford Shoes

This combination of a grey suit and a white and red vertical striped dress shirt is truly smart and creates instant appeal. Add a pair of burgundy leather oxford shoes to the mix and the whole ensemble will come together. When leaves are falling down and autumn is setting in, you'll love this combination as your uniform for transitional weather. The ability to rock outfits like this is one of the benefits of being middle-aged.

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Charcoal Wool Hat Black Sunglasses White and Blue Vertical Striped Dress Shirt Navy Tie Dark Brown Check Scarf Tan Leather Gloves Multi colored Houndstooth Overcoat Grey Plaid Suit Dark Brown Socks Brown Leather Tassel Loafers

For an ensemble that's absolutely Bond-worthy, consider teaming a grey suit with a white and red vertical striped dress shirt. We're totally digging how this whole outfit comes together thanks to brown leather tassel loafers. When leaves change color and autumn sets in, you'll love this outfit as your uniform for unpredictable fall weather. Amazingly stylish, this ensemble is also totally age-appropriate.

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Grey Wool Hat Clear Sunglasses White Vertical Striped Dress Shirt Violet Tie Dark Brown Check Scarf Navy Overcoat Grey Plaid Suit Pink Socks Dark Brown Suede Tassel Loafers

This pairing of a grey suit and a white and red vertical striped dress shirt can only be described as ridiculously dapper and polished. Add dark brown suede tassel loafers to the equation et voila, this getup is complete. As you can see here, it's very easy to look dapper and stay snug when colder weather arrives, all thanks to ensembles like this. This combination proves that figuring out how to dress stylishly at 40 and beyond is quite manageable.