Winter Dress Code

Earlier this year, I gave some advice corporate dress code. It was a tongue-in-cheek post about what a cool HR guy I am and offered some tips on how to define business casual vs Business dress. Well, the winter months are upon us, in Chicago, and I have some revised rules to that post. Fashion somewhat goes out the window and it’s all about warmth and function. So scrap everything you read and, for the next few months, follow this cool HR guy’s guide to the winter dress code.


If you know me, you know that shoes are my one true fashion love. It’s the first thing I look at when someone walks into a room and one of the first things I’ll compliment you on if you have some mad shoe game. And this still holds true for my winter dress code. Sort of. I don’t care what industry you’re in, if you have just a bit of an outdoor commute, you must have the proper shoes.

For those who have to wear a dress shoe and cannot leave them at the office or stuff them in a bag, protective rubber overshoes are a must. Salt and slush are the kryptonite to any great shoe. And even bathing your shoes in vinegar doesn’t fully get the salt stains out. So always use protection when battling the winter streets.

If you have some flexibility in your attire, make sure you have a good pair of boots. Ladies and gentlemen, you can never go wrong with a solid pair of Sorels. They’re warm and waterproof and add a little sizzle to that outfit. You can wear these all day if you feel like it. Also, a solid pair of hiking boots are totally acceptable for the all-day attire. I invested in these awesome Ecco boots and won’t take them off until March.


For those things to cover your lower extremities, anything fleece-lined will be a plus. Just go to Amazon and search “fleece lined pants” and you won’t be disappointed. You can be trendy and fashionable and you will always be toasty. If that’s not your thing, go old school and get a pair of thermal underwear. For you runners out there, those tights will do the trick on those sub-zero commutes.

Ladies, if you have to wear skirts or dresses, I hear the leg warmers are making a comeback. If that’s not for you, have no shame in sporting those Sorels all day. I’m not judging! As a matter of fact, you get extra points in my book for that move.


Here is where you have many options. I always recommend the layers when covering the upper body. Invest heavily in sweaters and quarter-zips. Flannel is always acceptable, and if you have a fleece-lined flannel, even better. I’ll be sporting the 15-year-old J-Crew cable knit sweat many times. And if you want to wear that button-up cable knit with the heavy collar, get cozy, my friend.

Ladies, those scarves are fantastic for this time of year. Gentlemen, don’t. The scarf is a must when walking outside. Just lose it when you get to work. Dust off the plaid wool blazer, just don’t accessorize with the scarf. Oh, and those zip up blazers are a great look.


Ok, bros, now is the time you can rock that stocking hat all day indoors. Hat hair is totally acceptable and expected in that 8am staff meeting. If you’re worried about your hair, ear muffs are fantastic. Wear a thick hat to protect your noggin from the falling ice.


Puffy coats and faux-fur lined hoods are a must. Get those coats that cover the backside to keep those parts warm. Thick gloves and scarves are needed to cover all parts of skin. North Face, Patagonia, and all types of Canadian goose down coats are in full effect.

The winter months are grueling. Chapped skin and cold toes are the norm for the next few months. But don’t let the cold weather keep you from being comfortable and warm. Layer up and keep that business jargon rolling as you breeze through the winter.


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