Wool Hat Smart Casual Outfits For Men After 40

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Grey Wool Hat Black Scarf White Vertical Striped Long Sleeve Shirt Black Leather Biker Jacket Navy Vertical Striped Chinos Tobacco Suede Chelsea Boots

For a casually stylish look, reach for a black leather biker jacket and a wool hat — these two pieces go nicely together. Tobacco suede chelsea boots are a fail-safe way to inject an extra dose of refinement into this ensemble. So if you're after dressing tips for gentlemen over 40, this pairing is perfect.

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Tan Wool Hat Hot Pink Check Long Sleeve Shirt Blue Plaid Scarf Black Leather Watch Blue Blazer Navy Skinny Jeans Brown Leather Oxford Shoes

We all look for comfort when it comes to styling, and this street style combo of a blue blazer and a wool hat is a great illustration of that. Go ahead and complement your getup with a pair of brown leather oxford shoes for a touch of elegance. So if you're in search of style ideas on how to dress as you step into your 40s, this getup is definitely worth saving for later.

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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

Marrying a blue blazer and a wool hat will prove your skills in men's fashion even on weekend days. Finishing with beige suede desert boots is a fail-safe way to bring a bit of zing to this ensemble. Wondering how to dress your age in your 40s? This combo is an amazing example.

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Black Wool Hat Black Scarf Dark Brown Shearling Jacket Black Crew-neck T-shirt Black Chinos Black Leather Casual Boots

A dark brown shearling jacket and a wool hat worn together are a sartorial dream for those dressers who love cool and casual styles. Put an elegant spin on this getup by slipping into black leather casual boots. A great combo as you transition into your forties.

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Black Wool Hat Black Sunglasses White Long Sleeve Shirt Burgundy Paisley Tie Navy Polka Dot Pocket Square Grey Chinos Brown Check Waistcoat Grey Wool Blazer Tan Pea Coat Brown Watch

A tan pea coat and a wool hat are bona fide essentials if you're planning a casual closet that holds to the highest menswear standards. This combo is your answer to the question of how to dress appropriately for your age as you pass the big 4-0.