The last of your kids have headed off to college, and you are officially an empty-nester. Congratulations! You finally have some time to focus on yourself. Will you work, travel or, perhaps, do a little of both? 

If work is in your future, it’s time to dust off the resume and figure out which industry can best use the experience you have honed over the years. Once that is narrowed down, and you have the job interview scheduled, what are you going to wear? Is a blazer and skirt still the proper attire for an interview?

Tricia Dempsey, former chief executive officer of Agile, an IT recruiting firm in Alpharetta, is a wealth of information. Dempsey also coaches women who are serious about reaching their career and life goals through her business Thrive-Her. 

“Up is not the next level,” she said about the women she coaches. Their next chapter is about being “more aligned with their purpose and strength.”

“It’s such a transitional time for dress for women [in the business world],” Dempsey said. “Without exception, no one is dressing up. When we are prepping candidates for interviews, we recommend something like a date-night dress.” 

Knee-length is the most flattering length, she said; but make sure the dress doesn’t hike up to your mid-thigh when you sit down. Sleeves are always a safe bet. Avoid lace, sequins or anything sheer, she advised. A closed-toe shoe with a low heel (not flats) is always in style. Wear understated jewelry to the interview. You want them to remember you, not your fabulous tassel earrings, she said.

“Too dressed up can put the customer or interviewer at unease,” Dempsey said. “Millennials as senior managers are wearing nice trousers and a blouse from Banana Republic or J Crew. That is at the top of their dress scale.”

Dempsey shared a recent meeting with one of her accounts in Utah.  

“[At Adobe], they are super chill,” she said. “It’s T-shirt and jeans every day. When I met with my client, he was in shorts. I wore a wrap dress and low heels. I felt very comfortable and confident.” 

Casual doesn’t mean sloppy

Dempsey mentioned a friend in an executive search firm, who dresses casually in jeans and a blouse in the office. While her look is casual, it is by no means sloppy. Every item is quality and fits well, and she said her friend looks sharp wearing them. She finishes the look with sandals, flats or low wedge boots, depending on the season. 

“VP and C-level types are a bit more dressy,” she said. “The lower staff is super casual.”

After you land the job

“Wear flats in the office and keep a pair of closed-toe or peep-toe heels in the car or desk drawer in case you need to meet with a client,” she said. 

When video conferencing, wear a solid bright color, and avoid small patterns such as herringbone that may not translate well on a digital format. If you are telecommuting from home via Skype or Zoom, your team can only see you from the sternum up. Make sure your hair and makeup is professional, and wear a nice blouse. No one will ever know you are wearing yoga pants or pajamas on your bottom half, she said.

Final tip

A casual dress code doesn’t mean casual hygiene. A professional and polished look from the neck up is vital to complete your overall “I’m dressed casually, but I mean business” presentation. Consider updating your hairstyle and makeup routine.


As a personal wardrobe consultant and owner of Alpharetta-based Fashion With Flair,  Lori Wynne helps people look their best. Connect with her at

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