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A grey denim jacket and olive chinos are absolute menswear staples if you're crafting a casual wardrobe that matches up to the highest sartorial standards. Spice up this outfit by slipping into a pair of dark brown leather casual boots. As you can see here, it's extremely easy to look dapper and stay toasty come colder weather, all thanks to combinations like this one. A fail-safe option pairing proper for gents in their 20s who like to dress more elegantly.

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For an off-duty ensemble, consider pairing a black wool shirt jacket with khaki jeans — these two items go pretty good together. When it comes to footwear, introduce dark brown leather casual boots to the equation. We love that this outfit is great come fall. As you're going from your 20s to your 30s, you want to start dressing like an adult man. In this case, looks like this prove useful as a source of inspiration.

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Swing into something casually smart and trendy with a grey shirt jacket and black chinos. Rounding off with a pair of dark brown leather chelsea boots is a simple way to introduce a bit of fanciness to this ensemble. This combo is the definition of ideal for when leaves are falling down and temps are falling. This outfit proves that figuring out how to dress well at 20 is quite manageable.

Tobacco Shoes Smart Casual Fall Outfits For Men In Their 20s: This outfit clearly shows it pays to invest in such smart menswear pieces as a grey double breasted blazer and black dress pants. Balance your ensemble with more casual footwear, like these brown suede boat shoes. This one is a viable option when it comes to planning a well-coordinated look for in-between weather. Smart casual combinations for stylish 20-something guys aren't actually that hard, as you see.

This outfit clearly shows it pays to invest in such smart menswear pieces as a grey double breasted blazer and black dress pants. Balance your ensemble with more casual footwear, like these brown suede boat shoes. This one is a viable option when it comes to planning a well-coordinated look for in-between weather. Smart casual combinations for stylish 20-something guys aren't actually that hard, as you see.

Tobacco Shoes Smart Casual Fall Outfits For Men In Their 20s: Such essentials as a grey double breasted blazer and black leather chinos are the perfect way to introduce a hint of masculine sophistication into your day-to-day fashion mix. Feel uninspired with this getup? Introduce brown suede loafers to switch things up. Can you see how very easy it is to look dapper and stay snug when chillier weather arrives, thanks to this outfit? This combination is the perfect answer to the question of how to dress as you move through your 20s.

Such essentials as a grey double breasted blazer and black leather chinos are the perfect way to introduce a hint of masculine sophistication into your day-to-day fashion mix. Feel uninspired with this getup? Introduce brown suede loafers to switch things up. Can you see how very easy it is to look dapper and stay snug when chillier weather arrives, thanks to this outfit? This combination is the perfect answer to the question of how to dress as you move through your 20s.