Flat Cap Smart Casual Fall Outfits For Men In Their 20s

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Beige Flat Cap Black Leather Messenger Bag Black Leather Gloves Beige Overcoat Beige Track Suit Black Leather Loafers

This street style combo of a beige overcoat and a flat cap is extremely easy to throw together without a second thought, helping you look sharp and ready for anything without spending too much time searching through your closet. For extra fashion points, introduce a pair of black leather loafers to the mix. This combo is the definition of perfect for when temps are dropping and autumn is in the air. All in all, a great demonstration of classic and casual style for young gents.

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Navy Flat Cap White Dress Shirt Dark Brown Tie Dark Brown Paisley Pocket Square Black Waistcoat Black Embellished Leather Belt Dark Brown Beaded Bracelet Navy Skinny Jeans Dark Brown Leather Briefcase Black and White Print Socks Dark Brown Leather Double Monks Dark Green Plaid Wool Blazer

A dark green plaid wool blazer and a flat cap are a cool combo to keep in your current casual rotation. For something more on the elegant side to complement this ensemble, add a pair of dark brown leather double monks to the equation. This one is an appealing choice when it comes to a killer summer-to-fall outfit. This outfit illustrates that dressing maturely and looking fashionable are not mutually exclusive things for a young guy.

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Grey Flat Cap Clear Sunglasses Charcoal Herringbone Overcoat Dark Brown Leather Belt Olive Jeans Black Leather Casual Boots

Team a charcoal herringbone overcoat with a flat cap for comfort dressing with a modern twist. Tap into some David Beckham dapperness and complete this look with black leather casual boots. As the temperatures get lower, you'll see that an ensemble like this is ideal for this time. A reliable option for 20-year-old guys looking for a more mature image.

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Grey Flat Cap Black and White Varsity Jacket Silver Bracelet Black Crew-neck T-shirt Black Leather Watch Black Jeans Black and White Leather Loafers

This combo of a black and white varsity jacket and a flat cap speaks comfort and fashion. If you want to feel a bit more elegant now, add a pair of black and white leather loafers to the mix. So when summer is done and autumn is here, this look has a good chance of becoming your go-to. A safe bet combo proper for men in their 20s who prefer to dress more elegantly.

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Grey Flat Cap Red and Black Check Shirt Jacket Black Leather Watch Black Jeans Black Socks Black and White Leather Loafers

The combo of a red and black check shirt jacket and a flat cap makes for a kick-ass laid-back ensemble. For something more on the classier side to complement this ensemble, complement your ensemble with black and white leather loafers. On not so cold afternoons, work this transitional ensemble and look absolutely amazing. Semi-casual looks for 20-something guys aren't actually that hard, as you see here.