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Becoming a Fashion Stylist at 45: Jennifer’s Story

Published on 06/17/2015

Jennifer Miller head shotAfter leaving the law, Jennifer returned to her first love, fashion, by starting a business helping women develop their personal style and curate their closets.

Tell us a little about your background…

My grandfather was an internationally renowned psychoanalyst; he was the head of Neurology at the University of Chicago and founded the Psychosomatic and Psychiatric Institute of Chicago, which was the first psychiatric hospital attached to a major medical center; he ran the institute for more than 50 years.

My father is also a psychoanalyst, while my mother stayed home to care for my brother and me.

at 12

Me at age 12

I have always been interested in fashion. I carried a purse at the age of 2, convinced my mother that she had to buy me a purple velvet top and skirt from Saks Fifth Avenue at the age of 9, and fashioned a denim mini-skirt using scraps of old jeans at 12. I moved from Chicago to New York City at 17 to attend Barnard College and spent weekends scavenging through racks in vintage clothing stores and frequenting trendy stores like Fiorucci and Reminiscence as often as possible.

I graduated with a double major in Sociology and English, then snagged a job at Glamour Magazine in New York, where I dispensed advice to readers on everything from “What type of top looks good with a pleated midi skirt?” to “What are the best clothes to hide my pear shaped body?” I answered all sorts of reader inquiries, from the deeply personal to common fashion issues.

After a year at Glamour, I was offered a position at Vogue Magazine, another Condé Nast Publication in the same office building. I was thrilled with this opportunity and stayed with Vogue for four years, moving up the ranks to copy editor. I was responsible for editing all of the magazine’s copy; no editorial content was published without my first reading it to make sure it was correct in grammar, syntax, and content.

At the age of 26, I moved back to Chicago to attend law school. It was just too hard to support myself on the $12,500 salary I made in publishing. I loved being a law student because it involved writing and editing but, once I landed a job at a law firm after graduation, I was quickly disenchanted. I had worked with mostly women at Glamour and Vogue so my first job in law was also my first one working with men. In the late 80s, it was hard to be taken seriously by male lawyers. As a fashionable young female lawyer, I found my work environment to be less than welcoming and extremely chauvinistic. I lasted a couple of years as an attorney before I’d had enough and quit the field entirely.


What is your next act?

I am a fashion stylist. I evaluate and edit clients’ closets on a regular basis before we shop. I shop weekly, monthly, seasonally with clients as their needs and finances allows. I help clients organize and pack for business trips and vacations. I am available by phone or text to choose outfits and accessories for a variety of events.

I charge an hourly fee regardless of whether we are working in a client’s closet or we are shopping. I charge much less than many stylists around the country and in Chicago, because most charge an hourly fee plus a commission on the clothing that is purchased—I don’t charge such a commission. As a result, I don’t encourage designer clothing over items from a less expensive store like the Gap because I don’t benefit from purchases. My income is solely based on the amount of time I am working with my clients.

In New York, hourly rates can be as high as $500 and I know a few stylists in Chicago who charge $400 an hour plus a commission. When I first started my business, I charged less than I do now but, as my expertise has increased, I have raised my rates and will continue to do so when it seems appropriate.

I get enormous pleasure from being with my clients and I feel a huge sense of pride in my accomplishments. One client recently told me “You saved me today; now I can go to my son’s graduation in a beautiful dress and travel with an assortment of new clothes.”



My wedding


I wore a Dolce and Gabbana jacket as a dress—with gold Manolo Blahnik slingbacks










How did you go from quitting the law to becoming a fashion stylist?

Around the time that I was becoming fed up with the law, I met my future husband, Jonathan. Well, the truth is, we’d gone to the same elementary school in Chicago; he was a grade above me and I had a crush on him at the time!

We married and had twin boys, Ezra and Caleb. When the boys were in nursery school, many of the young mothers I met learned of my background in fashion publishing and started asking for my advice on what to wear and how to wear it.

I began to help these women edit their closets and purchase outfits for various events and, soon enough, everyone I knew was calling me for assistance. At this point, my husband suggested that I start a business, but I didn’t feel ready. I had two young boys and I didn’t want to be distracted from raising them. It wasn’t until they were 9 years old and in the 4th grade that I decided to charge a fee for my work. I was 45 at the time.


Who are your clients and how do you find them?

The majority of my clients are women aged 40 to 70. I have recently begun to work with teenagers of both sexes, mostly children of clients or friends. I also work with the husbands of a few of my clients on a biannual basis.


Marsell shoes from Barneys

I have anywhere from 10 to 15 clients, many of whom have worked with me for several years now. When my clients’ spouses and children work with me intermittently, my clientele increases.

One of my regular clients lives in New York City and comes to Chicago once a year to shop with me. I send her links and recommendations throughout the year and suggest that she buy certain items in New York—so we work remotely the rest of the year. Now that my children are going to be in college in New York and Boston, I will most likely see her in person more often.


Delicate diamond necklace from Elements, Chicago

Recently a friend introduced me to her cousin from Israel, who was visiting Chicago; this new acquaintance has asked me to fly to Tel Aviv to do her closets! I am considering the offer; it is definitely the most remote place I have been invited to work so far.

I don’t market my services. Although I continue to work with friends, my clients find me through word-of-mouth recommendations. These women have ended up being my long-standing and most committed clients—and friends too. Last Christmas, I was at a party and a woman came over to me to admire my outfit. When I told her what I do she hired me on the spot to help her with her image.


How do you work with your clients?

When I first meet a client, I always recommend that we start in her closet. I like to examine every item of clothing that a client owns and assess it based on style, fit, and condition.



If an item has snags or looks worn, I always recommend we donate or discard it. If it is a designer piece that my client doesn’t wear any longer because it has gone out of style or is ill fitting, I recommend we try to sell it through Luxury Garage Sale or eDrop-Off, both luxury consignment stores in Chicago. That way, my client will make 60-65% of the agreed upon sale price if and when it sells.

I always preach quality over quantity and I live by that motto myself. I would rather have fewer items that are well made and classic than a closet full of poorly made, inexpensive pieces that I discard at the end of each season. Because my own closet is on the small side, I constantly edit out unwanted and unworn items. Whenever I buy a new piece of clothing, an old piece gets tossed, either for resale or donation.


Proenza Schouler

My approach to dressing includes classic clothes mixed in with more of-the- moment items. I encourage my clients to update their closets seasonally with colors and styles that are trending. Every woman should own blue jeans, white jeans, black trousers, a white cotton blouse, and long and short-sleeved t-shirts in an array of colors and prints. Right now, I love Vince t-shirts and Proenza Schouler tie-dye tee’s, which I collect every season. J. Crew made the perfect crewneck cotton sweater this season and I collected it in 4 different colors for myself and have convinced most of my clients that they have to buy at least one. Even my 90-year-old mother owns two of them!


J Crew

I also recommend day and evening dresses, skirts, jackets, and a trench coat. Those are just basic items, which I would elaborate on with each client depending on her lifestyle and whether or not she is engaged in a profession.

I love blazers and “moto” (motorcycle) jackets right now. I am collecting Veronica Beard blazers with zip-out dickeys resembling hoodies this season and have encouraged most of my clients to purchase one. They are an innovative way to wear a traditional blazer. If you remove the dickey, you have a standard navy or black blazer. With the dickey attached, you have a layered, more casual look.

I also love shopping for high quality resale items and vintage items at Vestiaire Collective and TheRealReal.com.

Roger Vivier sandals

Roger Vivier

Accessories are very important, but I have found that many of my clients stop at clothing and don’t understand (until I gently educate them) how jewelry, scarves, handbags, and shoes can elevate a look and provide individuality. A gorgeous sandal can elevate a basic pair of cropped jeans and a white t-shirt. This season, I purchased a pair of silver and irridescent Roger Vivier sandals which I intend to wear with casual and dressy looks. They are literally my signature item for the summer.


In my Veronica Beard blazer

Because I work alone without an assistant, I schedule my own hours. My business is busiest when clients are interested in shopping for their Fall/Winter and Spring/Summer wardrobes. I usually meet with a client two to six times per season because I find that if we work for more than five hours at a time, we both become exhausted. I would rather see a client for a few hours and then schedule another meeting a week or two later. I usually spend an hour or two in a client’s closet each season to weed out items before we embark on a shopping expedition, and then again after we have made purchases to help the client pair outfits together with accessories.


You say your father and grandfather’s work has influenced your approach. How so?

Their work in psychoanalysis informs my work as a fashion stylist. My approach is to be empathic and, by encouraging openness, to make sure that my clients feel comfortable with me, themselves, and their body image—a “retail therapy” of sorts.

When a client begins to work with me, I ask them questions to understand how they feel about their bodies, their clothes, and themselves. Knowing about my clients helps me to understand how far I can push them outside of their comfort zones and whether I can encourage them to try new styles they wouldn’t choose on their own. It is always a process, where my clients and I become comfortable with one another and they learn to trust me.

For example, I have been working with a client for many years. When we started together, she had a hard time imagining herself in anything other than the most conservative clothing: button-down shirts and trousers in solid, dark colors. She now wears colorful patterned dresses with heels and wedges, tops that are not a traditional button-down blouse (although we still buy them in more feminine fabrics and patterns), and all sorts of pants that range from narrow and cropped to wide and full.

Together, we have expanded her horizons and she is comfortable and excited about her new image. I have seen her self-confidence grow over time as her willingness to take fashion risks has developed. She used to walk into a party and cower in the corner; now she enters a room with confidence, smiling, and excited to be noticed and complimented on her appearance. My work with her has truly been retail therapy.


Marsell handbag from France

Marsell handbag from Blake, Chicago


Evening clutches, from high to low end: Behnaz Sarafpour (top), Calleen Cordero (middle), Lauren Merkin (bottom)










What’s hot in women’s fashion right now?

Right now I love Rag and Bone t-shirts and jeans, Frame denim, AG Jeans, and Lanvin and Celine slip-on skate sneakers.

Here is what I see trending for summer 2015: culottes, jumpsuits in silky fabrics, lace dresses and tops in white and cream, blue and white striped and oxford cloth shirt dresses, gingham dresses and pants, graphic pencil skirts that hit below the knee, loose and flowing Bohemian evening gowns, midriff-baring evening wear, cropped trouser suits, A-line earth tone skirts in suede and patchwork suede, florals, fringe, black and white prints, the colors yellow and army green, white denim with white t-shirts and polo shirts, one shoulder asymmetrical tops, wider leg denim pants that are cropped, denim overalls, delicate jewelry, platform sandals, and sport sneakers and sandals, which began to trend last summer and are continuing through this season.


Do you feel like you always have to “dress to impress” given your profession?

I do want to look well dressed when I am out and about in Chicago. I definitely think about whether or not I might run into a client or a friend, even when I am at Whole Foods doing grocery shopping. However, since fashion is a long time passion of mine, I have always made it a priority to be well-dressed and thoughtful about presentation.

That said, the minute I get home at the end of the day, I take off my street clothes and wear sweats! I buy loungewear at the Gap or Bloomingdales and throw on comfortable slippers or moccasins. I love loose fitting t-shirts and sweatshirts that I find at Gap or J.Crew just for relaxing in.  I love to be comfortable at home and encourage my clients to add these kinds of items to their wardrobes.

On off days and weekends, I love to wear Lululemon Street to Studio cropped pants in a variety of colors with a Madewell or J. Crew t-shirt and skate sneakers. I feel casual but put together at the same time. Lately, I have been sporting a bright pink pair of those Lululemon cropped pants with a white t-shirt and silver sneakers. Although I usually wear a lot of black, gray, and navy, I like to add a bold color for variety and these pink pants do the trick.

favorite jil Sander satin top

A favorite Jil Sander satin top


What challenges have you encountered? Who keeps you going?

One challenge is that friends ask me for advice on their closet edits and clothing but don’t want to hire me. I have had to draw the line and tell friends that I won’t work for free and that if they would like my expertise, then they will have to hire me.

My family is extremely supportive of my work and of what I have accomplished in the last 9 years. I do shop for my husband on occasion and sometimes for my sons but my boys, being fashionable 18 year olds, know what they like. They have actually introduced me to brands that I didn’t know about previously. They both love to shop at Barneys, RSVP Gallery, Vince, J.Crew, and Rag and Bone, as well as Opening Ceremony and Supreme in New York. They also shop online at Uniqlo.


What advice do you have for women interested in pursuing your profession?

I came to choose my profession after having been exposed to, and being interested in, fashion for several decades. My experiences at Glamour and Vogue were invaluable and gave me the tools to pursue my career. The best stylists are those who have had experience in retail or in the fashion industry.

The industry is unregulated and there are no classes, training programs, or national certification programs for becoming a stylist. I know a few women who are interested in starting a styling business and all of them have had retail experience.

I keep up with current fashion by regularly visiting stores, reading fashion magazines such as Vogue and Harper’s Bazaar, reading blogs like Garance Dore, The Sartorialist, and ManRepeller, and viewing websites like Style.com. I learn the most by being hands on in the stores. That way, I can see what is for sale and I usually develop a sense of what is trending for the season.

Jennifer Miller

What’s next for you?

I am currently developing a fashion blog, which I plan to launch sometime next year, after my twins leave for college. I find that I utilize certain concepts with all of my clients and I want to share this information with the public. I also find products each season that I think everyone should invest in and I look forward to having a platform where others can learn about my seasonal recommendations and “must haves.”


Contact Jennifer Miller at jen3100@comcast.net or at 312-259-5263.


HeleneTStelian Musing
I’m Hélène Stelian, the Midlife Mentor with a passion for facilitating personal development in women 40+. Through my THRIVE Courses, I help introspective, curious, action-oriented women 40+ deepen their journeys of self-discovery and growth—and create their next chapter with courage and intention.



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  1. Kimberly D Stiffle

    Brava Jennifer!

    • Jennifer Miller

      Thanks Kim. So glad you read it! I am thrilled to have an article about my business as I don’t typically market myself or what I do. Helene is such a thorough interviewer and writer. She was the perfect person to explore my work with me! Best, Jennifer

  2. Jennifer rpthman

    Great article!!! Jennifer

  3. Carilyn

    jen has been one of my fashion icons since way back. I was fortunate enough to be the recipient of one of the best hand-me-downs as a young girl, an angora puffy sleeved sweater from Ultimo, no less. Congratulations, on following your dream. The success is no surprise. xo

  4. Baroness von Kunzweiller

    Lovely. Helene, you are doing very important work for women of any age with your blog! I’m going to share it with a lot of women who need a little boost. Jen Miller has an eye, and your interview also revealed her heart. Playing a role in a business like fashion, which can often be so pretentious and superficial, Jen manages to keep the joy and fun of it all, like an old school glamor girl who takes it seriously but not too much so. Her real goal seems to be to help women be the best they can in order to bring confidence. I love to have her tips, and I keep them in mind when at my Salvation Army! Shhhh..

    • Hélène

      Thanks so much for reading and commenting! I love sharing the stories of women like Jennifer who get to midlife and pursue their passions. It’s so inspiring to me and to so many others who are asking “now what?”

  5. laura Front

    Excellent article about a very talented lady, congratulations, Jennifer!
    Looking forward to reading your blog

  6. Helen

    Great! It’s not easy to be a stylist, you must keep up with frequently changing fashion trends and ready to spend extra hours to meet deadlines.

  7. James Wrick

    Hi when i am searching on google about fashion i am reached on your site you have a such of nice content thanks for sharing it’s very helpful for me.



  1. Amazing Women Wednesday: Hélène Tragos Stelian | Travels with Tam! : Travels with Tam! - […] Becoming a Fashion Stylist at 45: Jennifer’s Story […]

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