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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:

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,



View Comments (11)
  • Sabir,
    I came across your site a few weeks ago, and I must say that you are killing it my friend! Your attention to detail, knowledge of fit/sizing is living proof that you don’t have to spend a fortune to be a well dressed gentleman. Continued success and keep the posts coming. Looking forward to seeing what you have in store for the summer months.
    Be Well,

    • Good Morning Carter,

      Thanks for dropping by the site and thanks for the kinds words. All of the things you mentioned are things that I take pride in while putting my clothes together and make all the difference in the long run. This summer will be sure to be filled with lots of fun looks.



  • very good style 🙂
    some considerations……my point of view:

    first outfit: very well combined: colors, and pieces: i d just change the jeans cut: not skinny one,but slim fit yes: the leg’s lenght matters: ankles shoes are not very easy to wear if the person is not very tall, i know it cause i ve got the same ” problem”. the point is that u should get some easy trick to lenghten ur silhouette.
    the jean’s crotch is loose,but ok: just the hem, the leg opening at the ankle,it’s too large to my eyes: at first sight, all the attention went to that part: there is too much jeans there, and u could easily dare wid a slim fit jeans, cause ur legs are fit but not extremely large:)

    second outfit: good job,especially for proportions.
    just…show the sleeves of ur pullover,
    and…but it’s just my personal point of view: say to the taylor to make slimmer ur trousers in the lower part: not much 😉

    third outfit: perfect combination of colors: compliments: u can go everywhere dressed like that in daily times:
    some consideration: don t be afraid to wear one size less: the look has its own rules even if sometimes is not very confy;) i guess ur belt is brown as ur boots are: show it out: would be much nicer to see, how shoes and belt matches together,so my advice is, take a smaller size for ur vest, and i appreciate the big v neck of the vest: it makes the upper part of your body longer: very good:
    and…as i wrote for the first outfit: boots… and jeans.. eh eh: just look at ur jeans: too much in the lower part, too fluffy: look at the distance between the crotch and the hem: looks short:
    some perfect pair of jeans for you would be:
    dolce&gabbana in 14 gold cut: perfect frontal rise and slim fit leg, first line black label i mean, not d&g that is the second line.
    prada slim fit: the same: good frontal rise and leg
    dior: but in this case, be careful cause dior make often high frontal rise,and the opening leg sometimes is skinny,but on google…type jude law dior…and u ll see what dior i advice for you.
    well..these jeans are quite expensive, but you could try even with.
    a.p.c petite standard
    or j.brand
    the coat is quite long: watch the proportions

  • You are a very stylish man who exudes confidence. I would like to purchase one of these caps. Thank you for the pointers, Ken.

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