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The Driving Cap

Three Driving Caps, Three Looks

Spring for me means a lot of things when it comes to style. One of the few things that I tend to gravitate toward when the weather is warm is a nice cap. My closet is outfitted with a few fitted caps, trucker hats and as you can see from this post driving caps. The driving cap has many names such as; Flat Cap, Jeff Cap and Paper boy cap to name a few. Mainly, I stick with the driving cap name because these caps remind me of the old (really old) race car uniforms when racers would wear these particular caps. Many people associate this caps with the working class folks of the late 19th century and early 20th century in the United States and London.

In general when wearing any kind of hat or cap there are some general don’ts:


  • Wear your hats/caps with sunglasses. These caps work to shield your eyes from the sun and you will look like a creep strolling around the streets (no one likes a creep).
  • Wear your hat indoors (specifically in a formal/work situation)
  • Wear your driving cap backwards (you will just look foolish and you are not Samuel L. Jackson)

Monochromatic Grungy:


Driving Cap and White Henley by Converse | Leather Jacket by Heritage | Grey Denim by Levi's | Belt by HM | Leather Wingtip Boots by Ritano

Adding an unstructured driving cap to a very relaxed look adds that boyish charm but can still give you some “bad-ass” attitude. Keeping the hat in the same color family as the rest of your clothing, will not make the hat stand out from the outfit. With a more relaxed look a driving cap with multiple patterns will not look out of place.

Side Note: Pick up a white henley. This shirt will carry your through the spring and summer and can be worn with a suit or denim.


Skull Bracelet from HM | Chrono watch by Goer | Watch Band by JCrew



Monochromatic Peacock:


Driving Cap and Blazer by HM | Black Leather Loafer by Robert Wayne | White Denim by Converse | Cashmere Sweater by Lands End |White Pocket Square by Geoffrey Beene

When pairing a driving cap with a dressier look you  will want to:

  • Make sure the hat is tighter and more streamline. This will fit will the tailored look of the outfit.
  • Keep the color and pattern of the hat consistent with the rest of the look.
  • Check to make sure the fabric of both your driving cap and blazer are similar. In this look, the driving cap and blazer are wool. Uniformity is sometimes a quality factor in a dressy look.

Browns and Blues:

See Also
S-Gents x Men's Style Pro x Sabir M. Peele

Driving Cap by London Fog | Trench with contrast buttons by HM | Jeans by Express | Brown Herringbone Waist Coat by Merona | Oxford Shirt by Izod | Brogued Boots by Asos

A brown driving cap is very versatile. This particular cap by London Fog is made of wool. Complimentary colors like blues and other shades of brown are great options when looking for a color scheme to rock this cap. This is my favorite driving cap because it does work well with a navy suit or can be thrown on with a pair of jeans and look great. You can probably tell that I keep my hair cut relatively short and these driving caps are a great option for keeping the breeze off of my head during this winter to spring transition.

Money Saving Tip:

The Converse cap, white jeans, grey Levi’s and herringbone waist coat were all picked up from Target. So you can get these items for pretty low prices and look great. The London fog hat I picked up from TJ Maxx for about $8. So don’t just jump at any item you see at all stores because you can get them cheaper if you are willing to be patient

Watch by Goer | Watch Band by J.Crew

Photo Credit: Marina T. Peele

Drive Safely in Style,



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