Do It on Friday
The last day of the work week is the obvious day to pull off a new fashion trend in the office. Give it a test, maybe once a month, and push the envelope. If there is not pushback, make it a casual Friday staple. Add to it a jacket, professional shirt (preferably button-down style), and dress shoes and see if your boss notices. If you do get caught, you can plead ignorance of the “casual” part of casual Friday rules. You also may want to have a second outfit ready to go in your vehicle.
Pair It with a Jacket
Jackets make everything and everyone look a little more professional, even college professors. By matching your dark blue jean joggers with a tailored jacket, you obscure the fact that you are pulling off wearing sweatpants to work.
Go Conservative on a Shirt
Shirts also can cover up a multitude of sartorial sins if you sure they make the entire look a bit more formal. Pick muted colors and patterns. Make sure your button-down shirt matches your joggers and that it is as professional as possible.
Wear Them on a Down Day at the Office
Plan to test out your blue and black joggers on a day where you will be spending most of your time sitting at your desk. Until you have mainstreamed wearing joggers to work, you should not wear them on a day you have to give a huge presentation to the boss. By planning to wear them on a down day at the office, you minimize office exposure, which leads to fewer people noticing.
Focus on Fabrics
Go with twill or other professional-looking materials for your joggers to give them a polished look. Do not wear patterns, as that draws attention to them. Match them with an all-business jacket, shirt, and shoes, and you will be able to pull it off with ease.
Jean joggers are essentially sweatpants that, when paired properly, can be worn in the office. The key is the pairing and the timing.