Leather Boots Chill Weather Outfits For Men In Their 20s

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Grey Print Hoodie Black Shearling Jacket Black Skinny Jeans Black Canvas Backpack Black Leather Chelsea Boots

For something on the casually cool end, try this combination of a black shearling jacket and black skinny jeans. Leather boots are an effortless way to upgrade this ensemble. Wondering how to perfect casual style as you move through your 20s? This combination is the perfect answer.

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Black Knit Wool Turtleneck Grey Scarf Camel Overcoat Light Blue Jeans Black Leather Chelsea Boots Black Socks Beige Suitcase Black Suitcase

Nail the effortlessly classic ensemble in a camel overcoat and light blue jeans. On the footwear front, this outfit is completed perfectly with leather boots. Overall, a perfect demonstration of semi-casual style for 20-something guys.

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Beige Beanie Tobacco Scarf Tobacco Wool Turtleneck Navy Overcoat Khaki Chinos Black Leather Casual Boots

Show that no-one does smart casual menswear like you by opting for a navy overcoat and khaki chinos. Our favorite of an endless number of ways to finish off this getup is with a pair of leather boots. As you're moving from your 20s to your 30s, you want to start dressing like a grown man. That's when outfits like this are a lifesaver.

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Burgundy Wool Turtleneck Beige Harrington Jacket Charcoal Plaid Chinos Black Leather Casual Boots

A beige harrington jacket and charcoal plaid chinos are a wonderful combo to keep in your casual arsenal. You can stick to a classier route on the shoe front by wearing leather boots. This getup shows how to kill in the smart fashion department as a 20-year-old gentleman.

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White Dress Shirt Black Tie Burgundy Pocket Square Black Sunglasses Black Leather Watch Black Wool Waistcoat Black Leather Belt Charcoal Wool Blazer Grey Chinos Black Socks Black Leather Chelsea Boots

This combination of a charcoal wool blazer and grey chinos couldn't possibly come across as anything other than ridiculously stylish and casually classic. If you don't know how to finish off, introduce a pair of leather boots to the mix. As you're getting to your 30s, you want to start dressing in a more elegant manner. That's when getups like this become a great source of inspiration.