Dressing Up Jeans

Jeans. For some people they symbolize lazy weekends; perhaps paired with your favorite old tee shirt and beat up sneakers. Perfect for washing the car or walking the dog. For others they connote urban hip; the ultimate counter play to formal office wear.

Ralph Lauren once made news when he wore jeans with his dinner jacket to receive a major award. Far from being social faux pas though, it was instantly understood to be a very “Ralph Lauren” look and launched a thousand failed imitators. What he made look sharp and fashionable most people simply butcher.

Jeans can be dressed up, but never make the mistake of thinking they can replace dress trousers, suit pants or, god forbid, tuxedo pants. People in the fashion business can get away with such things because they are in the fashion business and to their peers this is messing with the vernacular in a creative sort of way. Everyone else, myself included, should tread lightly when it comes to bringing jeans into the office.



Still, it is possible to dress up jeans for work, a nice dinner, or cocktail party. Just focus on some key rules.

You should own at least one pair of dark blue jeans; they are timeless and the most versatile type you can own. Dark blue jeans can be dressed up with a collared shirt, sports coat and brogues, or dressed down with a tee shirt, cashmere crew neck sweater and moccasins.

Remember this: even though they are just jeans, they should still fit you. I read a very funny article recently about “dad jeans,” which highlighted the sad fact that over the years most guys fail to buy new jeans and instead perpetrate a self-delusional myth that their favorites will always fit. They don’t; and while the jeans may stay in top form, you dear reader will probably not and it will show.

Although there are all sorts of fits and cuts, the best bet is still a basic strait leg version. It should sit at your natural hip and have a nice moderate break over your shoes. Alternately, you can wear them rolled up a bit for a preppy take or tailored to exactly hit the top of your shoe. Whatever your choice, they should look comfortable and trim but not tight; certainly not baggy and low-hanging. As with most things in life, simple is often better.



Dark jeans in particular lend themselves to more dressed-up outfits. They can carry off dressy casual better than their stonewashed or “vintage” brethren because of their inherent sophistication. In most outfits a good pair of dark blue jeans provides great texture and personality. Of course, if you want a laid back casual preppy look, most distressed and faded styles work fine as long as you stick with well-fitting strait leg models.



For the winter months, try pairing your jeans with a high quality dress shirt and sport coat – tweed or corduroy look great. Throw a vest in between to add some warmth as well as style. Trim jeans can carry off dress shoes particularly well. The juxtaposition of elegant leather footwear and rugged denim is very attractive.

For a more outdoorsy look, swap out the fine footwear for classic L.L. Bean Maine hunting boots. As noted above, jeans and sweaters are always a great mix.

By approaching a good pair of jeans as a part of your wardrobe and not just something thrown in the corner, you will get more out of this versatile workhorse.