Cool Weather Style: The Rumpled Look

To my mind, the cooler months are to men always the kindest when it comes to getting dressed in the morning. That's when we get to pull out the fun clothes and really take advantage of the many options that make classic menswear great. We get to layer.

I'm talking about stuff like chunky longwings, cords and a well worn jacket, topped it off with a warm cashmere scarf. The sheer variety of cold weather clothing is something many guys look to as the temperature drops.

For those of us with the flexibility to move between business dress and corporate casual, something I call the “Rumpled Look” is a nice middle alternative to being strictly dressed up or dressed down. Originally an offshoot of the American Preppy aesthetic, the rumpled look has come into its own. It's not an attempt to be sloppy, instead it is an homage to worn in classic comfort.



The basic idea behind this look 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.


Lapo: Master of the Stylish Rumple

This really is a fun look which is not hard to carry off well as long as you don’t try too hard. It's sort of the antithesis to the recent “critter” trend, which left every inch of pants, ties, belts and coats adorned with embroidered animals and icons of every sort – from dogs to martini glasses. Instead of sartorially hitting people over the head with your East Coast airs, stick to a less-is-more aesthetic. One creative article of clothing at a time is nicely ironic, more is overkill.


Simple but Classic

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 an un-ironed button down under a crew neck sweater should be just fine. For a younger look, don’t tuck in the shirt but rather let it hang out under the sweater - just make sure to choose a short bodied shirt. I've found that J. Crew button-downs are often just right. Wear a washed tweed jacket over the whole outfit. This kind of layering effect is another signature of the rumpled look.

Additionally, make sure to opt for clothes that actually fit well. The rumpled look is not an excuse to go baggy or oversized, it is more of a toned down and worn-in take on being well dressed.


Uncomplicated but still Detailed

One of the best things about this type of style is that you can effectively mix high and low to meet int he middle. For example, to meet up with friends for drinks, try pairing a permanently wrinkled (read, make a point of not ironing it) Thomas Pink dress shirt with dark but worn-in 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. What's most important is that you are 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.