White Dress Shirt with Chelsea Boots Smart Casual Chill Weather Outfits For Men After 40

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Navy Sunglasses White Dress Shirt Navy Tie Dark Green Fur Collar Coat Charcoal Plaid Chinos Black Leather Chelsea Boots

For a casually classic look, rock a white dress shirt with charcoal plaid chinos — these two items fit really well together. Avoid looking too casual by rounding off with chelsea boots. Dressed like this, any 40-year-old gentleman is bound to put many a younger man to shame.

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Dark Green Sunglasses White Dress Shirt Olive Print Tie Dark Brown Canvas Backpack Dark Brown Houndstooth Overcoat White Chinos Dark Brown Leather Chelsea Boots

Consider teaming a white dress shirt with white chinos to exude manly sophistication and polish. And if you need to instantly up the style ante of this ensemble with footwear, why not introduce a pair of chelsea boots to this look? So take cues and be the sharpest dressed gentleman in town.

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Dark Brown Sunglasses White Check Dress Shirt Grey Wool Waistcoat Navy Plaid Overcoat Navy Jeans Brown Leather Chelsea Boots Black and White Print Bandana

This combo of a white dress shirt and navy jeans will add alpha male essence to your ensemble. If you need to easily class up your look with footwear, why not complement this getup with chelsea boots? And if we're talking dressing ideas for middle-aged gents, this combo looks good on most guys.