155 Smart Casual Winter Outfits For Men In Their 20s

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Grey Knit Wool Turtleneck Olive Shearling Jacket Black Jeans Dark Green Suede Casual Boots

Consider pairing an olive shearling jacket with black jeans to don a cool and casual outfit. Class up this look with the help of dark green suede casual boots. In the colder months, when functionality is prized, it can be easy to settle for a less-than-stylish outfit. However, this outfit is a shining example that you can actually stay comfy and remain equally stylish during the colder months. If you want to present yourself like a grown man rather than a teenager, this is a great outfit to try.

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Dark Purple Baseball Cap Burgundy Horizontal Striped Turtleneck Tan Shearling Jacket Light Blue Chambray Long Sleeve Shirt Black Cargo Pants Brown Leather Casual Boots

This pairing of a tan shearling jacket and black cargo pants is definitive proof that a safe off-duty look doesn't have to be boring. Complement your outfit with brown leather casual boots to make the getup a bit more sophisticated. In winter, when warmth is paramount, it can be easy to surrender to a less-than-stylish outfit in the name of practicality. However, this outfit is a striking example that you can actually stay toasty and remain stylish in winter. As you're heading into your 30s, you probably want to start dressing like an adult. If that's the case, ensembles like this are a real lifesaver.

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Black Beanie Navy Denim Jacket Black Vertical Striped Scarf Black Leather Gloves Black and White Plaid Overcoat Charcoal Wool Chinos Black Leather Brogue Boots White Henley Shirt

A black and white plaid overcoat and charcoal wool chinos are among the fundamental pieces in any man's functional wardrobe. We adore how a pair of black leather brogue boots makes this look whole. This combination is equally neat and comfortable. Double win! Ideal to convey that even as a young adult you're confident enough to make your own sartorial choices.

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Olive Scarf Grey Wool Shirt Jacket Tan Cable Sweater Dark Brown Woven Leather Belt Camel Overcoat Olive Chinos Brown Suede Chelsea Boots

Showcase that nobody does classic and casual menswear like you in a camel overcoat and olive chinos. A pair of brown suede chelsea boots immediately ramps up the fashion factor of your look. During the colder months, when practicality is the priority, it can be easy to surrender to a less-than-stylish look in the name of convenience. This look, however, is a vivid example that you can actually stay cozy and remain equally stylish during the colder months. This combo demonstrates how to look stylish as you go through your 20s.

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White Dress Shirt Navy Tie Navy Denim Jacket Navy Fair Isle Sweater Vest Dark Brown Leather Belt Dark Brown Leather Watch Burgundy Corduroy Jeans Tan Leather Gloves Brown Suede Casual Boots Brown Overcoat

This combination of a brown overcoat and burgundy corduroy jeans couldn't possibly come across other than ridiculously sharp and casually neat. Introduce brown suede casual boots to the equation and the whole getup will come together. While it can be a bit challenging to stay on-trend on extra cold days, it's combinations like this that prove it's totally possible. And if we're talking fashion tips for 20-somethings, this getup looks good on almost any gent.