The Returner's Closet Conundrum

Blog by Beth Kawasaki, Co-Founder at ReBoot Accel.

ReBoot Accel has launched a Discussion Group on Facebook (please join us), and a member posted an article by Vicki Fagen titled “The Invisible One.” This started a let’s-get-real conversation about the closet conundrums women face when returning to a younger workforce following a career pause.

Vicki Fagan writes of her own interviewing experience,

I went for a job interview recently that was quite illuminating. Although I had applied for a plethora of positions in my field, it was rare to get a bite. It’s not that I lack experience, it’s just that as a woman in her 50s, I am part of an invisible demographic. They don’t know what to do with us.

The image accompanying the article (below) elicited a healthy, humorous, and even defiant dialogue that ranged from “going grey” as an impetus to entrepreneurship (who needs them anyway!?); to truly wondering if a cardigan is the kiss of death when worn in range of a Millennial.

One member commented,

I missed your presentation*, but do wonder about the appropriate dress part. I go with my gut, black pants, white blouse, more often than not, but wonder if I’m missing opportunities. What do different styles communicate? Does a cardigan damn me to subservience? What does trying to look “too hip” look like? And what about my hair? Sorry to be superficial, but I’ve lost the interview sometimes before it starts when they see I’m their version of old.

This is an important topic, because ageism is real and most women returning to the workforce following a pause are doing it primarily for a much needed paycheck, with high secondary hopes of personal reward and a positive impact. So, for those who need to get back to work NOW for financial and medical benefits, let’s get pragmatic and recognize that you may need to flex and update your look to enter and successfully engage with a new culture. How can we reduce the friction between the hiring manager at a company you want to work at, and you? Here is some sage advice about how to update your style without selling your soul.

The goal? TO COME ACROSS AS “CURRENT”. Not young. Not old. CURRENT.

The Personal Re|branding Begins NOW.

As soon as you’ve decided it’s time to return to work, even if there’s more discernment to do, ditch the yoga pants during the daytime and start rebranding yourself in the eyes of your closest contacts. Those friendly folks at your kid’s schools, on the city council, at your house of faith, etc. can serve as your first and most fruitful networks to new opportunities. Your personal update will provide visual clues to others that something is new with you, and either invite a conversation or support the one you initiate.

I like to tell the story of a lawyer, who following her ten year pause, was returning to work by starting her own boutique law firm. The first thing she did? Tossed the tennis togs. Her nearest contacts, and possibly first clients or best referrals, needed to see her shift from “tennis mom” to “law firm founder,” and her new professional presence helped them make that transition.

Context is Everything.

How do you know what “current” means in the context you’re trying to break into? Look to social media. Most companies run robust social media channels filled with photos and videos of their employees, their customers, special events, and more. Check out Visa’s Instagram account and you get a sense of who works there and what they value. Intuit’s Instagram accountreveals even more about how they build teams and a corporate culture. At minimum, if you are actively seeking work, follow the companies you’re targeting on Facebook, Instagram, and LinkedIn to get a look at who works there and what messages the company is choosing to share with the outside world.

A second source is GlassdoorGlassdoor is a jobs and recruiting site that allows the user an “insider’s look” into which employers are hiring, what it’s really like to work or interview there, and how much you could earn. It is a “give-to-get” model, completely free to join, but requiring community members to contribute a review within ten days to retain access. Since the review information is crowdsourced with refresh requirements, it is continually updated and feels much like a YELP for your career. Glassdoor is rich with photos and videos submitted by individuals, not the company. Here’s an example of how Glassdoor asks employees to post insider photos for Levi Strauss.


Last and best, ask around. Network your way to an individual currently working at the company you’re interested in and get first hand advice for the position you are working toward.

Note: How one dresses to get a job is different than how one may dress once you’re an employee. Generally speaking, the daily dress code can relax to the pervading culture after you’ve landed your job. Prior to that, the following tips from professional stylists will serve a returner well as she navigates her way to that success.

Five Personal Presence Tips I Learned from the Pros.

#1 Go Back to Black Basics. An up-to-date great fitting black pantsuit (jacket and slacks/skirt) is our best friend and investment for interviews, networking events, presentation, and pitching days. It can be dressed and ‘hipped” up or down. White button shirt for interviews, and T’s paired with jeans (or denim jacket with black slacks) for more casual days. Accessorized to reflect one’s personal style.

#2 Update Your Hairstyle. The hair thing, for better or for worse, is the number one recommendation stylists make for women returning to work. This advice lands sideways for some. I admit I highlight my hair. My grey is not great, and blending it makes me feel more confident. So whether you go grey or not, try for “current” in color and/or cut. This has become easier with match and mail services like Madison Reed. At home. Perfect match. Check it out.

#3 Evaluate Your Eyeglasses. This is the second most recommended update from professional stylists, and when you think about it, it makes sense. Making eye contact is a best business practice in most networking and interviewing settings, so eyeglasses are front and center right away. What do yours say about you? Check out current accessible styles at Warby Parker (with free at-home try-on) or upload your headshot and opt for a virtual try-on at Zenni.

#4 Take Advantage of Professionals. My waistline went AWOL awhile ago, so I have to work a little harder to find looks that read “current”. I use the Nordstrom FREE personal stylist (always) and tailoring services (many times free if you have their credit card) to source the right item and get the right fit. While you’re at it, stop by the Bobbi Brown makeup counter or contact Harvey Helms to get some help (and a pep talk) putting your best face forward. With these trusted vendors, you will still be you, just a refreshed better you.

#5 Shop the Fashion Food Chain and Rarely Pay Retail. I’m one of those fashion foragers who loves the hunt, visits Nordstrom Rack and TJMaxx monthly, and cruises online designer discount sites like GILT, especially for “current” shoes (my fashion passion). My colleague recently showed up to an event looking very “on-trend” in an impeccable black T (from Target, $12.99) and knit bi-color poncho (from Costco, $20). Professional stylists shop the fashion food chain too and observe that knowing how to mix high-low items in one’s wardrobe communicates currency, resourcefulness, and street savvy.

If you are open to reuse resources, here’s a story for you. One of our first ReBoot Accel success stories was a former engineer who was pivoting to the social impact sector. She assessed her new organization and the key constituencies she’d be interfacing with, then went to a local Goodwill Boutique, and sourced an astoundingly stylish and context appropriate wardrobe for a price she could feel great about.

If that’s not your thing, there’s a new resource out of Seattle, Style Your Armoire. A for-work. subscription-based, use-and-return model; or visit M.M.LaFleur a for-work clothing line for women of all stages and sizes (OP-22W), that comes with an online professional stylist to help pick the right pieces for your personal goals and style.

lisa flynn