Dress Shirt Fall Outfits For Men In Their 20s

Favorite

Unfavorite

Grey Sunglasses White and Navy Vertical Striped Dress Shirt Red Print Tie White Pocket Square Tan Waistcoat Red Leather Watch Olive Wool Suit Dark Green Socks Beige Suede Double Monks

Solid proof that a dress shirt and an olive wool suit are amazing when teamed together in a refined ensemble for today's guy. Go the extra mile and break up your look by wearing a pair of beige suede double monks. As you can see here, this ensemble is a really nice choice, especially for transeasonal weather, when the temperatures are dropping. This getup demonstrates that as a gentleman in his twenties, you have a wide range of styling options.

Favorite

Unfavorite

Dark Brown Sunglasses White Dress Shirt Olive Print Tie White Pocket Square Burgundy Leather Watch Red Beaded Bracelet Blue Jeans Dark Brown Leather Tassel Loafers Tan Check Waistcoat Tan Check Blazer

Marrying a dress shirt with blue jeans is a great idea for a casually classy outfit. Dark brown leather tassel loafers are guaranteed to bring a dose of sophistication to your look. As the mercury drops, you'll see that an ensemble like this is perfect for the season. Perfect if you're looking for some amazingly inspiring style for young guys.

Favorite

Unfavorite

Dark Brown Sunglasses White Dress Shirt Burgundy Knit Tie Burgundy Leather Biker Jacket Navy Vertical Striped Waistcoat Navy Vertical Striped Dress Pants Burgundy Leather Chelsea Boots

This combination of a dress shirt and navy vertical striped dress pants is the epitome of elegance. To inject a touch of stylish casualness into this getup, introduce a pair of burgundy leather chelsea boots to the mix. So when summer is done and fall is here, you'll find this getup to be your everything. Surely a goofproof choice if we're talking dressing ideas for 20-year-old gentlemen.

Favorite

Unfavorite

Yellow Check Dress Shirt Navy Tie White Pocket Square Brown Leather Watch Grey Waistcoat Navy Suit Brown Leather Double Monks

A dress shirt and a navy suit are absolute wardrobe heroes if you're piecing together a classic wardrobe that holds to the highest menswear standards. Let your sartorial skills really shine by completing your look with brown leather double monks. It's a viable choice if you're planning a well-coordinated look for transeasonal weather. So take cues and you'll be the sharpest dressed man your age.

Favorite

Unfavorite

Navy Knit Tie Blue Paisley Pocket Square Tobacco Leather Watch White Vertical Striped Waistcoat White and Navy Vertical Striped Blazer White Jeans Brown Leather Loafers Blue Chambray Dress Shirt

For relaxed sophistication with a masculine take, team a dress shirt with white jeans. Round off with a pair of brown leather loafers to power up this ensemble. It's is a savvy pick when it comes to an amazing transition ensemble. If you're in your late 20s, take cues from ensembles like this to take a more mature approach to your personal style.