Deconstructing The Look: Vintage inspired Smart Casual

A vintage look with a modern twist.

In the 1940s/1950s when tailored pants were well in vogue, it was common to see them paired with just about anything; including the classic leather jacket. This take on a vintage look gets a modernised touch with the addition of the colourfully adorned polo shirt and colourful socks.

Breaking Down the Look:

For each garment I have tried to find identical or similar alternatives so that you can shop the look if you like it!


Jacket: Kenneth Cole modular collar leather jacket, wearable either as a Harrington style (collar on) or racer style (collar off). I like to wear it sans collar as a racer jacket; I have found the collar part never seems to sit right when it is on. (similar)

Shirt: Ted Baker polo in navy with a red/blue patterned collar and button-through chest pocket which also features a small patch of print identical to the collar. This shirt also features a hidden button down collar, which is great since it gives the benefits of a button down without having to have the buttons visible.

Pants: Country Road cotton herringbone tailored pants with upturned cuff. (similar)

Socks: Red patterned socks which harmonise with the detailing on the polo.

Shoes: Vintage Timberland Earthkeepers brown leather chukka boots in a similar shade of brown to the jacket. (similar)

Watch: Citizen FA0024-53A two-tone quartz chronograph. This is my go-to daily watch, the two-tone makes it easy to pair with other accessories.

Colour Palette:

Brown, blue (various shades), grey and red.

Some takeaway tips from this look:

Choosing a colour for tailored pants

Grey pants used to be the casual wear equivalent of blue jeans today. If you are looking to add tailored pants to your casual rotation, a mid grey is a fantastic starting point as it works with just about any colour.

Statement Pieces

If you feel like your outfit is too plain, it is probably because it lacks a statement piece. A statement piece is the part of your outfit that catches the eye, and it does not have to be loud. In this outfit, the statement piece is the polo; this is a more subtle statement piece because it is only the detailing that really pops.

That’s all!

A vintage inspired look is fun to put together. Want to see more of this type of article? Drop me a line in the comments!

Photo credit for all shots (except wristwatch pic): Josh Thompson

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With content features ranging from appearances on popular menswear hubs (The Rake, StyleForum, Put This On) to French perfume newsletters and university course readings, Sam is a writer, designer and enthusiast in the fields of menswear and fragrance.

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