2. Casual Friday

Dark indigo jeans are the easiest to slide-in at the office, just make sure the fit and silhouette are similar to the suit’s matching trousers. This includes the hemline (rolling the bottom is a casual touch that won’t look as sharp with a business shoe).

Some tips to getting the perfect fit to dress-up your jeans:

- Save on the denim, spend at the tailor.

- Wear a tailored jacket shopping, or at least bring one from the floor into the fitting room.

- When you put them on in the fitting room they should be a little tight and restricting in the waist, hips, seat and thigh. I’m talking borderline uncomfortable. THEY WILL STRETCH. If they fit perfectly when you first put them on, in two weeks they will be looser than you want.

- Wear them for a couple weeks before having them tailored. You want to make sure they’re fully stretched out and the sizing has stabilized before making any alterations.

- Bring them to the tailor in worn condition (because your body molds them). One time I had a pair of jeans dry cleaned and brought them directly to the tailor still in the plastic bags from the cleaner. I tried them on and he marked the hem with no break, just how I like ‘em. I picked them up a few days later and after wearing them for a few hours the natural creasing at the back of the knee and front of the hips caused the denim to ride up about 3/4″, causing them to look “too short”.

- Once they’re tailored and fit just right, keep them away from the washing machine (which will cause them to shrink and fade). Instead, air them out, and when they get really nasty have them dry cleaned (rather than fading the denim the chemicals will gracefully enhance their natural break-in lines).