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

Favorite

Unfavorite

Black Crew-neck T-shirt Black and White Plaid Long Sleeve Shirt White and Black Houndstooth Overcoat Charcoal Check Wool Chinos White Socks Black Chunky Leather Derby Shoes

This combo of a crew-neck t-shirt and charcoal check wool chinos is a safe go-to for a devastatingly dapper ensemble. Wondering how to complete this getup? Finish with derby shoes to bump up the fashion factor. So as you can see, it's extremely easy to look awesome and stay comfy when cooler weather arrives, all thanks to looks like this one. Rest assured this ensemble is something you can totally wear as a gent in his twenties.

Favorite

Unfavorite

White Crew-neck T-shirt Navy Denim Shirt Jacket Tobacco Duffle Coat Charcoal Chinos Black Socks Black Leather Derby Shoes

This combo of a crew-neck t-shirt and charcoal chinos is a safe go-to for an absolutely cool ensemble. Don't know how to round off this ensemble? Rock derby shoes to kick up the style factor. This ensemble is the definition of perfect for when temps are falling and autumn is setting in. As a 20-year-old heading into your 30s, you'll love this outfit.

Favorite

Unfavorite

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

This laid-back pairing of a crew-neck t-shirt and navy jeans is extremely easy to throw together in next to no time, helping you look sharp and ready for anything without spending too much time rummaging through your wardrobe. Feeling venturesome? Elevate your outfit by finishing off with a pair of derby shoes. When you have one of those dreary fall days, sometimes only a cool look like this one can get you to face the outside world. As you're going through your late 20s, you want to start dressing maturely. If that's the case, ensembles like this are a winning option.

Favorite

Unfavorite

Black Beanie Clear Sunglasses Black Print Crew-neck T-shirt Grey Plaid Long Sleeve Shirt Brown Trenchcoat Blue Jeans Charcoal Print Socks Black Chunky Leather Derby Shoes

Reach for a crew-neck t-shirt and blue jeans if you're after a look idea for when you want to look cool and relaxed. Complete this getup with a pair of derby shoes to take things up a notch. Keep the autumn anxiety away in a killer ensemble like this one. If you're in your early 20s, take cues from looks like this to add more maturity to your look.

Favorite

Unfavorite

Clear Sunglasses Burgundy Print Crew-neck T-shirt Brown Fleece Shirt Jacket Navy Jeans Grey Socks Black Chunky Leather Derby Shoes

To assemble an off-duty ensemble with an edgy spin, make a crew-neck t-shirt and navy jeans your outfit choice. And if you wish to immediately perk up your ensemble with one single piece, complete your outfit with a pair of derby shoes. We're loving how perfect this look is come fall. Classic and casual ensembles for stylish 20-something gents aren't actually that hard, as you can see.