‘Structured Casual’ Look

One of my favorite looks, regardless of changing fashions and trends is what I would define as “structured casual.” In contrast to the bohemian intellectual look, this style is more sophisticated and urbane as well as likely easier to coordinate with the items you already have in your wardrobe. It’s the ideal outfit for either a museum excursion, dinner date at a trendy restaurant, or even a fashionable casual Friday at the office.

The most important elements of this look are slim jeans paired with dressier items such as narrow-toed brogues, dress shirts, and ties. The jeans you choose should be tapered at the leg and dark-colored. Right now, there seems to be a trend towards cropped jeans that end right below the ankle so as to show off the shoe. Unfortunately, this is almost impossible without the aid of a tailor as almost all jeans are sized to the same insanely long length despite a varying waist measurement. Levis Matchstick Jeans ($138)


The shirt and tie combination are the driving force and also what give the look a certain elegance and refinement. Unlike the current trends, this look eschews plaid and flannel in favor of more classic styles. A white shirt with a high collar is clearly the most versatile choice but striped and other patterned shirts are other alternatives. Tucking the shirt in is an absolute must; the days of the slovenly un-tucked shirt are over. Though the skinny tie-look with a business suit is mostly finished, they still go well with this style. Solid Knit Skinny Tie ($50)

Substituting dress shoes instead of sneakers when wearing jeans is always encouraged, regardless of what style you are trying to emulate. For the “structured casual” look in particular, a pair of narrow shoes looks best with slim jeans. I wear this pair from To Boot New York on a daily basis and constantly receive compliments on them. The fading around the toe and back of the shoe is a cool effect that differentiates it from more traditional or banal brown shoes. It is important to note that even though you are wearing jeans, white socks are not permissible with dress shoes. Rather, you can display some creativity with your choice of socks, either opting for something colorful or just basic black/brown.

To complete this style, a belt is a necessity. While wearing jeans and a T-shirt offers much more discretion as to whether or not to include a belt, forgoing one when wearing a dress shirt looks remiss. Thin belts are the look to opt for as they generally work better with slim jeans.


For colder weather, adding a waist-length trench coat helps establish the lines that create the “structure” in this look. Other ideas for making the look more winter appropriate include either wearing a fitted cardigan or sweater over the shirt. Don’t be afraid to tuck your sweater into your jeans; rather than looking over thought, the clean lines created by this will make you look slimmer and better put together. Short Trench Coat ($130)