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A sharp combination of a black print crew-neck t-shirt and black chinos will bring confidence and you'll carry yourself with more self-assurance. Feeling transgressive today? Break up this look with a pair of tobacco leather chelsea boots. Think it's hard for 20-somethings to master smart dressing? This combo will prove you wrong.

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A brown harrington jacket and brown chinos make for the ultimate casual ensemble for today's gent. Balance out this ensemble with a more refined kind of shoes, such as these tobacco leather chelsea boots. Sport this getup to achieve a more mature look as a 20-year-old gentleman.

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This pairing of a dark brown blazer and white chinos is perfect for elegant settings. For a classier aesthetic, introduce tobacco leather chelsea boots to the mix. As you're transitioning from your 20s to your 30s, you probably want to start dressing maturely. If that's the case, ensembles like this come in handy.