Creating the Perfect Work Outfit Formula So You Don’t Have To

Written By: Jacqueline Rappa

Another weekend has come and gone, which means a new week of work outfits is ahead of us. Don’t get me wrong—I love getting dressed and experimenting with what’s in my closet; it’s one of my greatest joys. But I admit it can feel overwhelming at times, especially when striving to look professional and put-together for work. That’s why I’ve perfected this 5-day formula for the fall and winter months, designed for all the working women who want to appear chic, stylish, and still true to themselves—even on colder days. And if you don’t work five days a week in the office, even better! The more options, the merrier.

Laid Back Mondays

I know what you’re thinking—shouldn’t we start the week strong and bold? In my opinion, not necessarily. Maybe I had a crazy weekend, and the last thing I need is to squeeze into itchy stockings. Maybe I want to bring some weekend coziness into Monday. For me, that means loose trousers and a soft cardigan. 

The beauty of this look is not only its comfort but also its versatility. Experiment with colored cardigans or patterned trousers. The key is to choose relaxed-fit trousers to stay comfy all day, and a cardigan that’s soft (absolutely no itchiness allowed). Each week, switch up your accessories—try a skinny scarf as a belt, alternate between a leather and suede bag, or leave a few cardigan buttons undone to show a hint of a white tank underneath. This easy look is here to kick off your week with style and ease.

It’s All in the Details Tuesdays

And the key detail today? Your boots. A knee-length boot is the star of this outfit, setting the tone for the whole look. On Tuesdays, we’re building around these boots—they’re the main character, and they deserve the spotlight. That means we’re opting for a skirt to really show them off. Since it’s the office, a midi skirt keeps things polished and refined.

On Tuesdays, let the boots do the talking, so no need to overthink the rest. Try a neutral-colored skirt, maybe even denim, and pair it with a top that makes you feel great—whether it’s a button-down, turtleneck, or cap-sleeve tee.

Matchy Matchy Wednesdays

This might be the best day—and I’m a bit biased because I love a good matching set. Midweek is the perfect time to pull one out for a little boost. You’ll feel elevated and ready to handle anything the day throws at you. Plus, matching sets are easy to find, whether you’re shopping at your go-to store or hunting for a gem on Depop or at the thrift store. That pinstripe office power suit you’ve been saving? Wear it. That matching maxi skirt and top? Bring it out. And if you don’t have a matching set, go for a monochrome look to create the same vibe.

Statement Sweater Thursdays

Would it even be the cooler months without a statement chunky sweater? It’s time to channel your inner Meg Ryan or Rory Gilmore. This time of year, sweaters have endless styling possibilities. Pair a classic cable knit with jeans and your favorite sneakers—hot latte in hand—and you’re effortlessly the office cool girl. It’s Friday Eve, so we’re keeping it laid-back as we ease into weekend mode. Whether your sweater is oversized, fitted, or off-the-shoulder, the style is all yours to play with.

Not-So-Casual Fridays

We’ve all heard of casual Fridays, but as the bold, non-conforming women we are, we’re redefining it. Fridays are for dresses. Why? Because we have plans after work—happy hour, friend date, first date, or dinner. And with one of our favorite dresses, there’s no need to rush home to change. It’s convenient, stylish, and effortlessly transitions from day to night.

Since it’s the colder months, these dresses are a little different from our spring and summer go-tos. Think cozy knit maxis or layer-friendly styles. If you don’t have a warm dress, try layering with a shirt underneath or adding a sweater vest on top. The more details, the more captivating the look.

As we move through the workweek, finding a balance between style, comfort, and professionalism can feel like a daily challenge. But with a simple, curated formula, dressing for the office becomes less of a task and more of a ritual you can look forward to. Each day offers a new way to feel confident and express yourself, whether it's through textured layers, bold details, or classic sets. So next time you’re staring into your closet on a Monday morning, remember—you already have everything you need to feel powerful all week long.