Men's Looks & Outfits: What To Wear In a Dressy Way

Dressy
Any weather/season
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Something as simple as opting for a navy wool blazer and charcoal wool dress pants can potentially set you apart from the crowd. Mix things up by wearing dark brown suede desert boots. This is a goofproof option for a kick-ass winter-to-spring getup.
Dark Brown Suede Desert Boots Black Socks Charcoal Wool Dress Pants Navy Wool Blazer Navy Vertical Striped Tie Light Blue Dress Shirt Brown Print Pocket Square
Navy Wool Blazer Light Blue Dress Shirt Charcoal Wool Dress Pants Dark Brown Suede Desert Boots Navy Vertical Striped Tie Brown Print Pocket Square

Something as simple as opting for a navy wool blazer and charcoal wool dress pants can potentially set you apart from the crowd. Mix things up by wearing dark brown suede desert boots. This is a goofproof option for a kick-ass winter-to-spring getup.

Go for a dark green check wool blazer and black chinos to look classy but not particularly formal. Polish off the ensemble with dark brown leather double monks. Seeing as temperatures are starting to drop, this outfit seems a sensible choice for in between seasons.
Black Flat Cap White Dress Shirt Dark Brown Wool Tie Charcoal Pocket Square Black Waistcoat Dark Green Check Wool Blazer Dark Brown Leather Double Monks Black Socks Black Chinos Dark Brown Leather Briefcase
Dark Green Check Wool Blazer Black Waistcoat White Dress Shirt Black Chinos Dark Brown Leather Double Monks Dark Brown Leather Briefcase

Go for a dark green check wool blazer and black chinos to look classy but not particularly formal. Polish off the ensemble with dark brown leather double monks. Seeing as temperatures are starting to drop, this outfit seems a sensible choice for in between seasons.

For a nothing less than incredibly stylish outfit, dress in a navy check blazer and an olive waistcoat. Rest assured, this getup will keep you comfy as well as looking seriously stylish in this unpredictable fall weather.
White Dress Shirt Red Lapel Pin Navy Paisley Tie White Pocket Square Olive Waistcoat Navy Check Blazer
Navy Check Blazer Olive Waistcoat White Dress Shirt Navy Paisley Tie White Pocket Square Red Lapel Pin

For a nothing less than incredibly stylish outfit, dress in a navy check blazer and an olive waistcoat. Rest assured, this getup will keep you comfy as well as looking seriously stylish in this unpredictable fall weather.

A modern man's sophisticated closet should always include such stylish essentials as a grey wool blazer and a light blue dress shirt. So if you're after an ensemble that's sharp but also totally spring_friendly, you found it.
Pink Floral Lapel Pin Light Blue Dress Shirt Multi colored Floral Tie Grey Wool Blazer
Grey Wool Blazer Light Blue Dress Shirt Multi colored Floral Tie Pink Floral Lapel Pin

A modern man's sophisticated closet should always include such stylish essentials as a grey wool blazer and a light blue dress shirt. So if you're after an ensemble that's sharp but also totally spring_friendly, you found it.

Pairing an olive check wool blazer and a violet waistcoat will create a powerful and confident silhouette. When it comes to dressing for transeasonal weather, nothing beats a kick-ass look that can take you from season to season.
Violet Vertical Striped Dress Shirt Red Knit Tie Purple Paisley Silk Pocket Square Violet Waistcoat Olive Check Wool Blazer
Olive Check Wool Blazer Violet Waistcoat Violet Vertical Striped Dress Shirt Red Knit Tie Purple Paisley Silk Pocket Square

Pairing an olive check wool blazer and a violet waistcoat will create a powerful and confident silhouette. When it comes to dressing for transeasonal weather, nothing beats a kick-ass look that can take you from season to season.

Nail that dapper look with a grey herringbone wool blazer and black wool dress pants. This combo is absolutely perfect to welcome spring.
White Dress Shirt Dark Green Polka Dot Wool Tie Brown Paisley Pocket Square Dark Brown Leather Watch Grey Herringbone Wool Blazer Black Wool Dress Pants
Grey Herringbone Wool Blazer White Dress Shirt Black Wool Dress Pants Dark Green Polka Dot Wool Tie Brown Paisley Pocket Square Dark Brown Leather Watch

Nail that dapper look with a grey herringbone wool blazer and black wool dress pants. This combo is absolutely perfect to welcome spring.

Go for a black suit and a black fair isle crew-neck sweater for a sharp classy look. Consider brown leather double monks as the glue that will bring your outfit together. This ensemble is a wonderful pick come warmer weather.
White Pocket Square Black Suit Brown Leather Double Monks Black Fair Isle Crew-neck Sweater
Black Suit Black Fair Isle Crew-neck Sweater Brown Leather Double Monks White Pocket Square

Go for a black suit and a black fair isle crew-neck sweater for a sharp classy look. Consider brown leather double monks as the glue that will bring your outfit together. This ensemble is a wonderful pick come warmer weather.

For a nothing less than incredibly stylish ensemble, marry a beige shawl cardigan with navy dress pants. An outfit like this is ideal for awkward transition weather.
Light Blue Dress Shirt Navy Tie Beige Shawl Cardigan Silver Watch Brown Leather Belt Navy Dress Pants
Beige Shawl Cardigan Light Blue Dress Shirt Navy Dress Pants Navy Tie Brown Leather Belt Silver Watch

For a nothing less than incredibly stylish ensemble, marry a beige shawl cardigan with navy dress pants. An outfit like this is ideal for awkward transition weather.

Try pairing a navy cardigan with olive dress pants like a true gent. A pair of dark brown leather derby shoes ads edginess to a classic style. Keep this look ready to go when spring comes, and we guarantee you'll save a ton of time getting dressed on more than one occasion.
White Print Dress Shirt Navy Cardigan Olive Dress Pants Dark Brown Leather Derby Shoes Tobacco Leather Belt Navy Tie Brown Leather Watch
Navy Cardigan White Print Dress Shirt Olive Dress Pants Dark Brown Leather Derby Shoes Navy Tie Tobacco Leather Belt

Try pairing a navy cardigan with olive dress pants like a true gent. A pair of dark brown leather derby shoes ads edginess to a classic style. Keep this look ready to go when spring comes, and we guarantee you'll save a ton of time getting dressed on more than one occasion.

Pairing a navy overcoat and grey wool dress pants will create a powerful and confident silhouette. A pair of dark brown leather derby shoes ads edginess to a classic style. This one is an exciting pick if you're putting together a knockout look that will take you from summer to fall.
Dark Brown Check Scarf Navy Overcoat Silver Watch Grey Wool Dress Pants Dark Brown Leather Derby Shoes
Navy Overcoat Grey Wool Dress Pants Dark Brown Leather Derby Shoes Dark Brown Check Scarf Silver Watch

Pairing a navy overcoat and grey wool dress pants will create a powerful and confident silhouette. A pair of dark brown leather derby shoes ads edginess to a classic style. This one is an exciting pick if you're putting together a knockout look that will take you from summer to fall.

Team a camel overcoat with black dress pants for a classic and refined silhouette. Want to go easy on the shoe front? Throw in a pair of dark brown leather chelsea boots for the day. So when summer is over and autumn is settling in, this getup has a good chance of becoming your favorite.
Grey Knit Turtleneck Camel Overcoat Black Dress Pants Dark Brown Leather Chelsea Boots
Camel Overcoat Grey Knit Turtleneck Black Dress Pants Dark Brown Leather Chelsea Boots

Team a camel overcoat with black dress pants for a classic and refined silhouette. Want to go easy on the shoe front? Throw in a pair of dark brown leather chelsea boots for the day. So when summer is over and autumn is settling in, this getup has a good chance of becoming your favorite.

This combo of a brown plaid wool blazer and beige chinos will add a graceful essence to your outfit. Rest assured, this look will keep you warm as well as looking stylish in this summer-to-fall weather.
White Dress Shirt Beige Tie Brown Silk Pocket Square Tobacco Waistcoat Brown Plaid Wool Blazer Beige Chinos
Brown Plaid Wool Blazer Tobacco Waistcoat White Dress Shirt Beige Chinos Beige Tie Brown Silk Pocket Square

This combo of a brown plaid wool blazer and beige chinos will add a graceful essence to your outfit. Rest assured, this look will keep you warm as well as looking stylish in this summer-to-fall weather.

Consider wearing a brown plaid wool blazer and navy chinos to achieve a dressy but not too dressy look. A comfortable transition outfit like this one makes it very easy to welcome the new season.
White Dress Shirt Black Knit Tie Beige Print Pocket Square Brown Plaid Wool Blazer Black Wool Waistcoat Navy Chinos
Brown Plaid Wool Blazer Black Wool Waistcoat White Dress Shirt Navy Chinos Black Knit Tie Beige Print Pocket Square

Consider wearing a brown plaid wool blazer and navy chinos to achieve a dressy but not too dressy look. A comfortable transition outfit like this one makes it very easy to welcome the new season.

Consider teaming a navy and green plaid blazer with grey wool dress pants to ooze class and sophistication. We love how great this one is for summer-to-fall weather.
Light Blue Vertical Striped Dress Shirt Navy Knit Tie Navy Print Pocket Square Olive Wool Waistcoat Navy and Green Plaid Blazer Grey Wool Dress Pants
Navy and Green Plaid Blazer Olive Wool Waistcoat Light Blue Vertical Striped Dress Shirt Grey Wool Dress Pants Navy Knit Tie Navy Print Pocket Square

Consider teaming a navy and green plaid blazer with grey wool dress pants to ooze class and sophistication. We love how great this one is for summer-to-fall weather.

This combination of a violet plaid wool blazer and navy wool dress pants is the picture of elegance. You can rest assured this combination is ideal for fluctuating autumn weather.
Burgundy Tie White Dress Shirt Dark Brown Pocket Square White Crew-neck Sweater Violet Plaid Wool Blazer Navy Wool Dress Pants
Violet Plaid Wool Blazer White Crew-neck Sweater White Dress Shirt Navy Wool Dress Pants Burgundy Tie Dark Brown Pocket Square

This combination of a violet plaid wool blazer and navy wool dress pants is the picture of elegance. You can rest assured this combination is ideal for fluctuating autumn weather.

Go for a classic style in a dark brown check wool blazer and navy dress pants. These picks will keep you warm and stylish in summer-to-fall weather.
White and Black Vertical Striped Dress Shirt Dark Brown Paisley Tie Dark Brown Pocket Square Dark Brown Check Wool Blazer Grey Plaid Wool Waistcoat Navy Dress Pants
Dark Brown Check Wool Blazer Grey Plaid Wool Waistcoat White and Black Vertical Striped Dress Shirt Navy Dress Pants Dark Brown Paisley Tie Dark Brown Pocket Square

Go for a classic style in a dark brown check wool blazer and navy dress pants. These picks will keep you warm and stylish in summer-to-fall weather.