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This combination of a black long sleeve t-shirt and black skinny jeans is solid proof that a simple casual outfit doesn't have to be boring. A trendy pair of chelsea boots is the simplest way to upgrade this ensemble. This outfit is a viable option if you're putting together a standout look for in-between weather. This combo proves that moving through your late 20s is no reason to stop dressing casually.

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This pairing of an olive bomber jacket and black skinny jeans is super easy to put together and so comfortable to rock a version of as well! Chelsea boots are an effortless way to breathe a hint of elegance into this ensemble. Seeing as autumn is settling in, this getup is a viable idea for the transitional season. Those wondering how to pull off edgy casual dressing as you go through your 20s, you have your answer.

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We're all seeking practicality when it comes to styling, and this modern casual pairing of a brown suede biker jacket and black skinny jeans is an amazing example of that. If you want to immediately level up this ensemble with one piece, add chelsea boots to this outfit. This one is an obvious idea if you're piecing together an awesome transition ensemble. Wondering how to nail casual outfits as you cruise through your 20s? This pairing is a great example.

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