How to Transform Your Favorite Basics Into 5 Cool Winter Office Outfits

Welcome to Weekday Wardrobe, a series in which one Who What Wear editor or staffer will snap a pic of their 9-to-5 look each day and break down where you can shop it all to inspire your own office style.

I'll admit it: I much prefer dressing for the office during warm months. It's so much easier to throw on what is my personal go-to summer uniform: a mid-length dress with either sneakers, loafers, or flat sandals. However, I've been trying to make an effort lately to elevate my work wardrobe. By that I don't necessarily mean dressing ultra formal at the office, but rather switching up my outfits so I'm not wearing an almost identical denim-and-sweater outfit every single day of the week. This exercise has completely made me think how to style my wardrobe basics to create outfits that feel both interesting and office-friendly. Need a little inspiration of your own? Check out these five outfit ideas for your 9-to-5.


I typically put the most effort, or at least the most time, into my outfits on Mondays. This is mostly because we have an all-department afternoon meeting in which I would like to impress my boss, my boss’ boss, etc., but also because I have no excuse not to have had time to prepare something stylish the night before.

Here, I elevate my go-to jeans and black blazer with some on-trend details like moc-crock heeled boots, a leather knotted headband, and a belt to wear around my waist instead of hips. Pro tip: Instead of purchasing separate belts that fit around dresses and blazers at your waist than ones for your pants, get this $7 tool I found on Amazon that is essentially a leather hole puncher. It’s the cheapest item that I can say has changed my life (or at least my wardrobe).


I went to a Y7 yoga class right before work on this day, so I had to pack a gym-bag friendly outfit. I'm noticing now my jeans got a little wrinkled in transit (hey I tried!), but the idea is to avoid anything silky or bulky. Two-piece outfits, like this denim-and-sweater combo, is my go-to on days where I work out before heading into the office.

I chose this specific outfit because I love wearing head-to-toe neutrals, especially in winter when it's a little less expected and when all-black looks start to get boring. White boots aren't really practical in NYC unfortunately, so I chose these fun brown snakeskin ones instead to pair with my white tunic sweater and white jeans.

Everyone at the Who What Wear NY office has been wearing leather or faux-leather pants more than any other pants this season. I finally got a pair of my own about a month ago and I guess I'm a trousers person now because I wear these at least once a week.

These leather pants go with just about anything I'd wear black jeans with, making them really easy to style. I'm into navy-and-black outfit combos right now (and well, always) so I chose my navy mock-croc bucket bag and navy pinstripe blazer. Also, I'd like us all to please take a moment of silence for my perfectly white sneakers that are no longer perfectly white anymore.


I had dinner plans in walking distance after work this day, so I purposely wore comfortable flat boots. I've actually worn these combat-style boots so much the past few months with everything from denim to dresses.

Speaking of dresses, this one is short-sleeved so I layered a thick turtleneck bodysuit underneath in addition to wearing my slightly cropped leather jacket. Note that a bodysuit is key here as a regular shirt will ride up all day, which speaking from experience, is very annoying and distracting. I rest my case on the bodysuit.


I'm someone who really likes to honor the "casual" in "casual Fridays." For me, that means jeans are a given, and there will most definitely not be heels of any kind involved. It was a bit chillier out on this particular day, so I layered a turtleneck underneath my baggy knit in a shade that coordinates with my loafers. Speaking of the loafers, remember what I said about non-heeled shoes? These are my go-to for when sneakers would make my outfit just a bit too casual.

The accessories here are simple yet necessary: a Western-style belt that gives my black skinny jeans a little extra something and gold hoops with charms. I would also like to note, mostly to myself, that this was by far my best hair day of the week. But I digress.

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