Mastering the Rumpled Look

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Cooler weather is always more kind to men when it comes to getting dressed in the morning. We can layer, pull out the cords, throw on a chunky jacket and top it off with a warm scarf. The sheer variety of cool weather clothing is something many a man looks to as the thermometer drops.

For those of us with the flexibility to move between business dress and corporate casual, what I call the “Rumpled Look” is a middle alternative to just dressed up and dressed down. Originally an offshoot of the American Preppy aesthetic, the rumpled look has come into its own.

The basic idea behind this style is the allusion to old money, classic taste, and timeless style. Newer or continental styles don’t lend themselves to celebrating beat up and handed down clothes quite like the preppy culture does. The unspoken message of the slouchy khakis, un-ironed oxford shirt and slightly beat up shoes is that you have old money, an Ivy League education, a summerhouse in the Hamptons, and you sail a lot. Or at least you dress like you do.

I have to say that this really is a fun look which is not hard to carry off well as long as you don’t try too hard. Like the current “critter” trend, with pants, ties, belts and coats are adorned with embroidered animals and icons of every sort – dogs to martini glasses – less is more. One creative article of clothing at a time is ironic, more is overkill.

For most men, wearing this look at the office can be a bit tough, but depending on your company’s culture, distressed chinos matched up with a wrinkled button down under a crewneck sweater should be just fine. For a younger look, don’t tuck in the shirt but rather let it hang out under the sweater. Wear a washed tweed jacket over the whole outfit. This kind of layering effect is another signature of the rumpled look. To meet up with friends for drinks, try pairing a permanently wrinkled Thomas Pink dress shirt with dressy jeans and a sport coat. The juxtaposition of classic and casual is a key balance to this look.

Like any other style you want to incorporate into your own, stop and look in the mirror before leaving the house. You want to be happy with the overall feel and proportion of your outfit. The goal should be to look like you’ve had everything for years and don’t think twice about getting dressed.


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Chris Hogan, an association executive based in Washington, D.C., blogs at OffTheCuffDC.com. A lifelong interest in style and clothing led to sales and management positions at several Ralph Lauren stores and an active wardrobe consulting practice