Dark Brown Derby Shoes with Crew-neck T-shirt Smart Casual Fall Outfits In Their 20s

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Grey Sweatshirt Black Plaid Overcoat White Crew-neck T-shirt Black Chinos Black Socks Dark Brown Leather Derby Shoes

This combination of a crew-neck t-shirt and black chinos is super easy to put together and so comfortable to rock a version of throughout the day as well! If you need to effortlessly elevate your look with shoes, why not complement your outfit with a pair of dark brown derby shoes? When leaves turn yellow and red and autumn is in the air, you'll appreciate how great this ensemble is for transeasonal weather. Think it's hard for gents in their 20s to nail semi-casual looks? This combo should prove you otherwise.

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White Crew-neck T-shirt Tan Raincoat Brown Leather Belt Charcoal Wool Suit Black Socks Dark Brown Leather Derby Shoes

This combo of a crew-neck t-shirt and a tan raincoat is super versatile and up for whatever's on your to-do list today. Rounding off with a pair of dark brown derby shoes is a surefire way to infuse a touch of class into your look. When you have one of those dreary autumn days, sometimes only a cool look like this one can get you to face the outside world. As you're approaching your 30s, you want to start dressing like an adult. That's when ensembles like this are a real lifesaver.

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Navy Crew-neck T-shirt Beige Long Sleeve Shirt Black Leather Shirt Jacket Grey Plaid Wool Chinos Dark Brown Leather Derby Shoes

This combination of a crew-neck t-shirt and grey plaid wool chinos makes for the perfect base for a multitude of dapper ensembles. If you need to immediately elevate this look with one single piece, why not complement this ensemble with dark brown derby shoes? Seeing as the weather is getting chillier with each day, this ensemble seems a savvy idea for the transitional season. A fail-safe option ensemble appropriate for 20-something gents who like to dress more elegantly.

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Charcoal Print Baseball Cap Grey Crew-neck T-shirt Olive Print Long Sleeve Shirt Grey Bomber Jacket Dark Brown Leather Watch Navy Jeans White Socks Brown Suede Derby Shoes

A crew-neck t-shirt and navy jeans are both versatile menswear must-haves that will integrate well within your casual styling routine. Go ahead and add dark brown derby shoes to the mix for an extra touch of style. When temps are dropping and fall is settling in, you'll love this combination as your favorite for unpredictable fall weather. A no-brainer getup proper for guys in their 20s who like sleeker ensembles.

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Burgundy Long Sleeve T-Shirt Olive Field Jacket Beige Crew-neck T-shirt Olive Chinos Dark Brown Socks Brown Leather Derby Shoes

When the situation allows laid-back dressing, consider pairing a crew-neck t-shirt with olive chinos. Let your styling expertise really shine by rounding off your ensemble with dark brown derby shoes. We're loving that this combo is ideal when colder weather hits. As you're moving through your late 20s, you want to start dressing more like a mature gentleman. That's when getups like this are a foolproof option.