White and Red Vertical Striped Shirt Chill Weather Outfits For Men After 40

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Brown Beanie Brown Sunglasses Tan Scarf Beige Pea Coat White and Red Vertical Striped Long Sleeve Shirt Olive Dress Pants White Leather Derby Shoes

Consider pairing a white and red vertical striped shirt with olive dress pants - this look is bound to make an entrance. You could stick to the classic route on the shoe front by finishing off with white leather derby shoes. A safe bet ensemble appropriate for over-40 guys.

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Navy Beanie White and Navy Vertical Striped Dress Shirt Dark Green Puffer Jacket Green Sunglasses Navy Corduroy Suit Navy Socks Brown Suede Desert Boots

This combo of a white and red vertical striped shirt and a dark green puffer jacket looks awesome, but it's very easy to achieve. Go ahead and complement your look with brown suede desert boots for a sense of polish. The ability to sport outfits like this is one of the advantages of being middle-aged.

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White and Blue Vertical Striped Dress Shirt Navy Pocket Square Orange Cable Sweater Dark Green Wool Blazer Dark Brown Corduroy Dress Pants Violet Socks Brown Suede Desert Boots

We love the way this pairing of a white and red vertical striped shirt and dark brown corduroy dress pants instantly makes any guy look dapper and elegant. Finishing with a pair of brown suede desert boots is a fail-safe way to introduce some extra definition to your look. Wondering how you should dress as you step into your 40s? This getup is a perfect example.

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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

This pairing of a white and red vertical striped shirt and a multi colored houndstooth overcoat is a never-failing option when you need to look seriously stylish and sophisticated. Want to go all out with shoes? Introduce brown leather tassel loafers to the equation. So if you're looking for style inspiration for dressing as you go into your 40s, this pairing is definitely worth saving for later.

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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

For manly elegance with a modernized spin, you can easily wear a white and red vertical striped shirt and a navy overcoat. Make this ensemble slightly more polished by finishing off with dark brown suede tassel loafers. This ensemble demonstrates that figuring out how to dress stylishly as a mature gentleman is easier than one might think.