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 occasional appearances on popular menswear hub social accounts (The Rake, Styleforum, Put This On) to French perfume newsletters and university course readings, Sam is an enthusiast, designer and writer in the fields of menswear and fragrance.

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