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Why not consider pairing a teal satin bomber jacket with grey houndstooth chinos? As well as totally functional, both of these items look great when paired together. Complement this getup with a pair of clear low top sneakers and the whole ensemble will come together perfectly. As you can see, this ensemble is a really smart pick, especially for transeasonal weather, when the mercury is dipping. All in all, a perfect example of laid-back fashion for gentlemen in their 20s.

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This pairing of a black quilted leather biker jacket and grey houndstooth chinos is the ideal balance between functional and dapper. Clear low top sneakers integrate well within a ton of combinations. As you can see, this look is a really wonderful choice, especially for transeasonal weather, when the temps are dropping. Those who are curious how to pull off edgy off-duty dressing as you make it through your 20s, you have your answer.

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A black and white print crew-neck sweater and blue ripped skinny jeans are the kind of a winning off-duty look that you need when you have no extra time to pick out a look. For maximum style, introduce a pair of clear low top sneakers to the equation. When it's one of those gloomy autumn days, what better to spice it up than a on-trend ensemble like this one? This combo demonstrates that progressing through your late 20s is no reason to stop dressing casually.

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If you love relaxed dressing, why not take this combination of a black shearling jacket and black ripped skinny jeans for a walk? Clear low top sneakers are the simplest way to punch up this look. Can you see how extremely easy it is to look sharp and stay cozy when fall arrives, thanks to this getup? This outfit shows how guys in their 20s kill in the style department.

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