5 Dapper Winter Outfits For Men #winterfashion #fallfashion #mensfashion #streetstyle
May 31, 2024

5 Dapper Winter Outfits For Men

What does a dapper outfit really mean? Simply put, to dress dapper is to dress smart. You are not dressing to make an obvious impression, really. You are dressing in a neat, concerted way, such that your appearance has an understated but suave charm to it. It is the best way to dress really, no matter the season or the time of the year.

Of course, with winter outfits dressing in a dapper way can be a bit of a problem. And it is do with the number of layers that one has to wear. Simply because the number of layers that you are going to be wearing during intense winters, for instance, is going to be quite something. So, you have to make sure each individual element of your outfit complements the others.

To figure out the tricks of the game, check out our guide to winter outfits and how to do them in a dapper manner

  • Our Most Favourite Look - Black Jeans + Grey Sweater + Blue Fur Winter Jacket + Black Monk Shoes
  • Occasion - Daily wear, street style, Business casual
  • Featured - ROWANROW
  • Budget - Medium to high. As some jackets featured here can be super expensive. 
  • Age Group - 20 to 40 years 
  • Recommended Read - More Winter Outfits For Men
  • Recommended Guide - Capsule Wardrobe For Men (eBook)

Dapper Winter Outfits For Men

5 Dapper Winter Outfits For Men

Outfit 1

This one pairs the classic biker jacket with a pretty straightforward combination of elements. If dapper implies neatness, then this outfit is the perfect example of how one can look dapper with minimalistic elements. The cream tee adds a softer color to the whole look, while the biker jacket, the ripped denims and the black sneakers add a layer of edge each.

The biker jacket here has a belt at the waistband, so make sure the belt for your denims is not visible – otherwise it can give the appearance of two belts, and that messiness can take away from the dapper appeal of the look. Pair this with black sneakers to complete the look.

5 Dapper Winter Outfits For Men #winterfashion #fallfashion #mensfashion #streetstyle

Outfit 2

This one has an unmissable gentlemanly, old-world charm to it. To maintain the charm throughout the outfit, keep the color palette of each individual element on the darker, moodier side. The long grey overcoat is the statement piece here, so the white shirt and the wide neck cardigan that form the other layers of this look have to be understated.

Long coats can give you a very flattering silhouette if you let the rest of the elements of your outfit have a snugger fit. Add a touch of contrast with the brown suede shoes, and you can also balance the shoes with a brown weekender bag.

5 Dapper Winter Outfits For Men #winterfashion #fallfashion #mensfashion #streetstyle

Outfit 3

The statement piece of this look is the navy-blue puffer jacket with the dramatic brown fleece collar. So, keep the rest of the elements in this outfit minimalistic. The woolen cardigan that forms the base of this look also acts as the balancing element here – with its stone grey color, it complements the blues, browns and blacks of the look.

Puffer jackets can be styled really well in moodier color combinations like this one, and brown and blue make for a really underrated, dapper combo. The black pants and the black formal shoes anchor the outfit, adding a classic charm that complements the dapper impact of the jacket.

5 Dapper Winter Outfits For Men #winterfashion #fallfashion #mensfashion #streetstyle

Outfit 4

The base of this look is all white, so make sure you keep it clean to retain the charm of the look. White pants can be particularly tricky to style, because they can very easily come across as pyjamas. To avoid this, go for white trousers that have a flattering silhouette, whatever their fit might be.

The one here has a slim fit. This outfit styles the white base with a denim jacket and a biscuit overcoat, both of which add a freshness to the look, bringing it closer to a wintry color palette despite the whites. Style this with a pair of black shoes and you can also add a brown backpack to make this look more fashionable and functional.

5 Dapper Winter Outfits For Men #winterfashion #fallfashion #mensfashion #streetstyle

Outfit 5

In this fifth outfit, pay attention to the colors introduced by each individual element and how well they complement each other despite not having the exact same tone. The ochre overcoat, the grey waistcoat, the white shirt, the dark blue denims, the brown shoes – each add a certain color to the look, but the outfit balances it out.

The ochre of the coat and the blue of the denim are the two central colors here, while the rest of the colors add more and more charm to the look.

5 Dapper Winter Outfits For Men #winterfashion #fallfashion #mensfashion #streetstyle

5 Dapper Winter Outfits For Men #winterfashion #fallfashion #mensfashion #streetstyle

5 Dapper Winter Outfits For Men #winterfashion #fallfashion #mensfashion #streetstyle