An Interview with a Stylist: Deeper than Fashion

September 24, 2018

Fashion Week just ended in NYC, fall is officially here, and award season is upon us, which means there’s lots of beautiful eye candy being produced from the fashion world these days.

All of this has me inspired to think about what I might add or take away from my wardrobe, and I’ve also been intrigued by what it’s like to be the people who dress the famous and stylish. Thankfully, I’ve got a super talented costume designer/stylist friend who agreed to sit down with me and give the inside scoop on styling and tips for how to approach the way we dress.

Pamela Shephard-Hill, Costume Designer, Stylist and Educator

What made you pursue a career in fashion?
I’ve always loved fashion, but when I was younger, I never had an example of how you make a living in this industry. I come from a family of very traditional paths, so I decided to pursue degrees in computer science and math in college. After graduating, I worked in graphic design, because I was drawn to the arts. But it was clear I was on the wrong path, because I had no interest in learning how I could get better. One day, I got into a very bad car accident. And while sitting on the side of the road, I called a girlfriend and decided I was going to move to New York and pursue fashion, with $600 to my name. For my first six months in New York, I stayed with my friend in BedStuy, and I somehow felt like I was rich, and that the sky was the limit. That was 12 years ago.

On needing just one ‘yes’
I had a colleague from college who gave me the bible of contacts in fashion. PR people, designers, showroom contacts, stylists. And I emailed everyone on the list. If there were 1,000 people on the list, maybe two people responded. But you really only need one. I started working in editorial, and then I moved on to doing visual merchandising for Macy’s, which is essentially arranging things to create an environment that helps the buyer understand the product and feel encouraged to purchase it. From there, I went on to style interiors and displays for Girbaud and later for Donna Karen nationally.

On what people think she does vs. what she actually does

As a stylist and costume designer, people think I just buy clothes and put them on people. They don’t know I’m in pre-production meetings, and I sit with line producers and accountants to go over budgets. I spend a lot of time reaching out to my contacts, managing logistics and transport, delegating, and getting people on the same page. It can be very intense. It’s very physical work, and a major sacrifice is sleep. Weekends are precious for my husband and loved ones, because the work hours are long during the week. We have a lot of early call times, and if I’m styling for TV (Pam recently worked as a costume designer for the show The Rundown with Robin Thede), it’s very long days.

I start with research, and I learn a client’s personality and silhouette to build something very unique and flattering to her. We source clothes from rental houses, showrooms, and department stores. I shop, and I conduct fittings with multiple looks. We try it on, see how it feels, and consider what the movements will be before making a final decision.

On why styling is deeper than just fashion
There are few things that are more intimate than dressing someone. It requires a lot of humility, because a stylist is often on his or her knees. In my role, I have to make make people feel safe, comfortable, and heard. And the creative aspect is no doubt a part, but the human aspect of it is that much more.

On how storytelling should shape the way you shop and dress
I love storytelling, and I love visually creating a narrative, using fashion. What story do we want an outfit to tell? In the case of Robin, her sketches were often rooted in comedy, so we’d want to include little details that would inject humor. Some days I’m trying to tell a story–today (in the outfit pictured) is a bit of a more whimsical swing.

On today’s fashion trends
Women are very much in this mode of comfort. I see and sense that. It’s not just in “alternative style”–it’s popular fashion to have on denim that’s not suffocating or a top that allows you to breathe. It’s very en vogue to be comfortable.

On her favorite designers
On the high end, I love, love, love Yohji Yamamoto. I also love Rodebjer and Dries Van Noten – they all have whimsy and structural interest. In terms of more accessible designers, I love COS and Helmut Lang.

On developing her own personal style
My personal style has been developed out of function. A lot is the routine of my life and what is effortless and easy to put together. There are certain silhouettes constantly repeated in my wardrobe, which are informed by my height and knowing what I feel polished in. I am a fan of uniforms–white shirts, hard denim, navy, black. Personal style should be informed by knowing your lifestyle and needs.

I’m so grateful to Pam for sharing some of her journey and insight into her world. I love the concept of asking ourselves, “What story am I trying to tell?” when we get dressed/buy something. Have you found anything particularly helpful in developing your personal style?

You Might Also Like...


  • Reply
    September 25, 2018 at 12:27 pm

    What an exciting profession! And my personal style is pretty eclectic since most of my clothes are gifts from hubby and others!

    • Reply
      Jessica Rice
      September 28, 2018 at 8:19 am

      I agree, Ma! Such an interesting profession. And Pops does a great job of picking clothes for you! It’s clear he’s figured out what looks good on you. :-)

  • Reply
    October 15, 2018 at 9:17 am

    The “Sitting on the side of the road” is what captivated me about the journey. All of us have bumps in the road but how many of use go on to recover. Wow, what a motivating article. It leaves me saying if she can, so can I. Thank you for this reminder.

  • Reply
    October 15, 2018 at 3:43 pm

    Grateful for this because it’s timely. My oldest daughter is pursuing a career in fashion and I love being able to show her people who look like her who are doing what they love. I love showing her there are so many different avenues and areas in fashion.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.