Plaid Flat Cap Chill Weather Outfits For Men After 40

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Grey Plaid Flat Cap Dark Brown Sunglasses Light Blue Vertical Striped Dress Shirt Navy Polka Dot Tie Dark Brown Barn Jacket Charcoal Socks Brown Leather Double Monks Dark Brown Dress Pants

Rock a dark brown barn jacket with a plaid flat cap to create an urban and absolutely dapper look. Take a more polished approach with footwear and introduce brown leather double monks to this look. A great ensemble as you transition into the next stage of your life, your 40s.

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Grey Plaid Flat Cap Clear Sunglasses Light Blue Check Dress Shirt Burgundy Polka Dot Tie Brown Suspenders Tan Plaid Wool Blazer Dark Brown Leather Watch Brown Corduroy Dress Pants Dark Brown Leather Brogues

A tan plaid wool blazer and a plaid flat cap combined together are a wonderful match. Balance out this getup with a more sophisticated kind of footwear, like these dark brown leather brogues. A no-brainer ensemble appropriate for middle-aged guys.

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Brown Plaid Flat Cap Dark Brown Sunglasses White Dress Shirt Charcoal Tie Tobacco Plaid Wool Blazer Brown Suede Gloves Brown Check Scarf Brown Barn Jacket Brown Dress Pants Dark Brown Socks Brown Suede Tassel Loafers

This casual combo of a brown barn jacket and a plaid flat cap is clean, seriously stylish and very easy to replicate. Put an elegant spin on an otherwise all-too-common getup by sporting brown suede tassel loafers. This combo illustrates that figuring out fashion at age 40 is not particularly hard.

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Grey Plaid Flat Cap Dark Brown Sunglasses Light Blue Vertical Striped Dress Shirt Orange Floral Tie Dark Brown Leather Watch Olive Barn Jacket Dark Brown Check Scarf Navy Jeans Dark Brown Leather Brogues

An olive barn jacket and a plaid flat cap are absolute essentials if you're putting together a casual wardrobe that holds to the highest style standards. A great pair of dark brown leather brogues is the simplest way to add a little kick to the ensemble. Overall, a great insight into dressing as an over-40 gent.

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Grey Plaid Flat Cap Dark Brown Sunglasses Light Blue Dress Shirt Navy Tie Grey Plaid Blazer Dark Green Barn Jacket Dark Brown Leather Watch Charcoal Dress Pants Navy Socks Dark Brown Suede Tassel Loafers

This combination of a dark green barn jacket and a plaid flat cap is uber stylish and provides a cool and casual look. In the footwear department, go for something on the smarter end of the spectrum by rocking a pair of dark brown suede tassel loafers. Combos like this have a refined air that befit 40-something guys really well.