Planning a week’s worth of stylish outfits can be a challenge, especially for working women with jam-packed schedules. From board meetings to bar meet ups, the modern boss lady has got to find a weekly wardrobe formula that can accommodate both her career and her social calendar. The best place to start? Looking to other women who have pulled it off for inspiration.

Below, see how Cynthia Andrew, a lawyer by day, blogger by night, crafts a 5-day outfit spread with 2 dresses and a leather jacket.

The Pieces


Staying true to her elegant, yet alluring personal style, Cynthia chose 3 pieces that were equal parts sophisticated and playful. Her week’s calendar consisted of lots of work-related functions, so she gravitated towards dresses that would help her make a professional impression. But her schedule didn’t stop there. Cynthia also had a few more casual events during the week, so she selected a leather jacket that could easily edge up her look. Scroll to see how she got creative to pull off this balance.

The Schedule

Monday: A Day Full of Board Meetings


Cynthia proves dressing for a big meeting doesn’t have to be boring. In fact, the power player feels it’s a chance to make a statement: “A well-made red dress demands attention,” Cynthia explains. To put her effortless fashion girl spin on the red Prabal dress, Cynthia finished the look with a circle leather tote and gold accessories. The final outfit is perfection, don’t you agree?

Tuesday: Post-Work Trip to a New Museum Exhibition

As a NYC dweller, Cynthia always has somewhere to be after her 9-5. This week she’s headed to check out a new art exhibition at her favorite museum. For this trip, she kept it nice and casual, pairing the Asilio jacket with boyfriend jeans and a crisp white oxford for a cool downtown vibe. This tried and true trio always looks put together and can be adapted to accommodate any personal style.

Wednesday: Serving as a Panelist for a Career Fair at Her Alma Mater


Midweek, Cynthia went for classic with a twist. She paired the graphic Antonio Berardi dress with black accessories — with chic tassels, of course — to create an elevated ensemble for her appearance at her alma mater. This combo gave Cynthia the extra boost of energy to attend the panel with authority: “You can’t help but be confident in this black and white number. It’s such a standout piece.”

Thursday: Lunch with Her Mentor


Thursday brought a much needed catch up with Cynthia’s dear friend and professional mentor. Their lunch date didn’t call for a specific dress code — it wasn’t business casual, but not quite brunch-chic — so she opted for something in the middle. She got a second wear out of the polished Prabal Gurung dress by styling it with streetwear accessories, throwing on a denim jacket and a navy polka-dotted neckerchief.

Friday: Happy Hour with the Girls


For Cynthia, Fridays are a chance to have fun with more casual styles. After finishing up at the office, Cynthia used her leather jacket to create a fall-friendly look fit for a chill girl’s night. “This dress is so flirty and girly,” Cynthia explains, “and works really well paired with a tough leather jacket and boots.” Give her approach a try with your own wardrobe this week by pairing a feminine piece with biker-inspired accessories. It’s a super easy way to master day-to-night dressing.

Try updating your own wardrobe by mixing in 3 new pieces from Rent the Runway Unlimited. Share your own story updating your look on Instagram by tagging #thanksitsRTR.