Red and White Print Pocket Square Dressy Fall Outfits In Their 30s

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Burgundy Print Pocket Square Burgundy Dress Shirt Black Leather Belt Grey Wool Blazer Black Leather Watch Dark Brown Leather Gloves Grey Plaid Trenchcoat White Dress Pants Brown Leather Chelsea Boots Burgundy Print Silk Scarf

A grey plaid trenchcoat and a red and white print pocket square are an easy way to inject played down dapperness into your daily routine. Introduce brown leather chelsea boots to this look to instantly jazz up the look. This getup is an exciting option when it comes to a cool summer-to-fall ensemble. This is a nice yet age-appropriate pairing for a 30-something Millennial gentleman.

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Brown Sunglasses White Dress Shirt Red Knit Tie Red Print Pocket Square Red Overcoat Navy Vertical Striped Suit Dark Brown Leather Watch Tan Leather Gloves Dark Brown Socks Dark Brown Suede Oxford Shoes

If you gravitate towards relaxed combinations, why not wear this pairing of a red overcoat and a red and white print pocket square? Step up your ensemble by finishing with a pair of dark brown suede oxford shoes. If it's one of those gloomy fall days, what better to spice it up than a dapper look like this one? As a 30-something Millennial guy, you probably want to start dressing with more class. In this case, looks like this are a never-failing option.

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Light Blue Vertical Striped Dress Shirt Grey Tie Burgundy Print Pocket Square Black Waistcoat Grey Herringbone Blazer Navy Horizontal Striped Canvas Watch Charcoal Dress Pants Black Suede Oxford Shoes

Irrefutable proof that a grey herringbone blazer and a red and white print pocket square are awesome when combined together in a street style getup. Finishing with black suede oxford shoes is a surefire way to add some extra flair to your getup. This outfit is a wonderful idea when it comes to picking out a knockout outfit for transitional weather. Combos like this have a sophisticated air that suit 30-year-old gentlemen really well.

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Pink Vertical Striped Dress Shirt Grey Horizontal Striped Tie Burgundy Print Pocket Square Dark Purple Cardigan Navy Horizontal Striped Canvas Watch Tan Houndstooth Blazer Grey Wool Dress Pants Navy Print Socks Dark Purple Leather Tassel Loafers

A tan houndstooth blazer and a red and white print pocket square are the kind of a foolproof casual outfit that you so desperately need when you have no extra time to put together an outfit. Our favorite of a multitude of ways to finish this ensemble is a pair of dark purple leather tassel loafers. So as you can see, this combo is a really wonderful pick, especially for summer-to-fall weather, when the temperature is dropping. And if we're talking dressing ideas for maturing men, this outfit is ideal.

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Light Blue Dress Shirt Navy Tie Burgundy Print Pocket Square Navy Leather Watch Navy Plaid Blazer Black Waistcoat Navy Dress Pants Dark Brown Leather Oxford Shoes

A navy plaid blazer and a red and white print pocket square are essential in any modern gentleman's great off-duty closet. Dark brown leather oxford shoes are a guaranteed way to bring a touch of polish to your look. As you can see here, it's super easy to look on-trend and stay comfortable when chillier weather comes, thanks to this outfit. This one is a modern and mature combo for a gentleman in his thirties.