Hello, my 9 to 5ers. How was your first day back at school, the office? At my job, the last two weeks of December are blissfully slow. Everyone’s working from home and most things are Q1’s concern. When I was working, I wore exclusively soft pants. But not today. Today was the first Monday of the new year, so we’re all back at the office, sitting at our desks, fully dressed at 9:00 am.
As a kid, the first day of school was exciting because I had a fresh haul of new clothes to debut. I started the week with an outfit planned for every day. Now, the closest thing to the first day of school feeling is the first Monday of the year. Aside from the usual dose of Sunday Scaries, I was actually looking forward to getting dressed and seeing what Christmas gifts people were wearing.
Here are the honorable mentions.
After a meeting about KPIs from 2024 and OKRs for 2025, I was chatting with a co-worker about the real debate of the day: Should her new black loafers be worn with jeans or trousers? My answer was, “Yes.”
Outfit sources: Pinterest
With jeans
With trousers
Next up was a surprising contender. A tan men’s shacket from Costco. Yes, Costco! Now that I look it up, apparently, it’s Banana Republic. Add this to your grocery list next time you pick up a rotisserie chicken. See for yourself
Continuing with men’s fashion – An interesting choice was a trucker hat, on a Monday. My usual preference is to start the week dressed more professionally, then go increasingly casual as the week goes on. My only question is, was the trucker hat intentionally selected to hide the bags under your eyes from staying up too late to watch Harry Potter like I did?
If you’re going to go with a trucker hat, why the hell not go with Von Dutch
Now, this next one was clever. I imagine this being her decision process to get dressed.
- Reaches for favorite matching jammies.
- Regretfully remembers she has to go to the office.
- Looks for the next best option.
- Decides on a matching set.
A solid pick to transition from holiday mode to work mode, in my opinion.
For my choice, I stomped through the parking garage all the way to my stand up desk wearing my new black chelsea boots paired with a black pleated skirt, and Sheertex tights that actually live up to the marketing hype. (I’ve had them for two years and they have zero snags.)
Getting dressed is meant to be fun. Make that one of your new year’s resolutions.
Cheers to the work week and a new year!
Sydney Styles 
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