Seeking Inspriato with Sheilagh Carlisle in Charleston, South Carolina
Cut
What are your favorite kinds of cuts? Why?
“Contrasting. I love wearing combat boots with a silk dress or a vintage t-shirt with a tailored blazer.”
Color
What are your favorite colors? The ones that you feel make your skin pop?
“Black anything. Or white. But then I like to blend in moody tones, jewel tones and metallics.”
Cloth
Favorite materials? Why?
“Natural or recycled. They are easier on the planet.”
Comfort
What do you feel most comfortable in, while feeling Clothing Confident, and why?
“It depends. When I’m at work I like a strict uniform that’s pretty much black and white, sometimes gray. It helps me feel professional and limits my decision fatigue during the week. But in my personal time I feel most Clothing Confident when I’m wearing what feels like a one-of-a-kind outfit — something you couldn’t find on any shop-front mannequin. I like to pick up items at thrift stores, vintage shops, and through our Naked Lady Clothing swaps and then mix and match.”
I love people, I really do. It’s rare I meet someone I dislike.
But even more rare is to meet someone I feel really connected with.
A “where have you been all my life?” connection.
Meeting Sheilagh was that. She was introduced to me (virtually) by way of a mutual friend, Sofia (read Sofia’s Seeking Inspirato).
Sheilagh has a heart of gold, and she works and acts accordingly.
Not only is she Director of Development for Habitat for Humanity, she is also one of the proud founders of the Naked Lady Society, a free, Charleston-based clothing swap.
Their mantra is:
“Clean out your closet, support local causes, and update your wardrobe in an environmentally friendly way.” - nakedladysociety.org
It’s minimalist. It’s socially conscious. It’s developing Dynamic Personal Style. This is such stuff that Seeking Inspirato dreams are made on.
I met up with Sheilagh at the neatest cocktail bar overlooking Charleston to talk about her love of clothing, and how she gives the gift of Clothing Confidence to other women through the Naked Lady Society.
Views from the Citrus Club in Charleston, South Carolina
Start Them Young
Sheilagh wanted to be a fashion designer when she was 8 or 9 and whiled away the hours sketching designs in her room. Later, in college, she worked a retail job at Madewell. Madewell had just started out and only had 5 locations.
Sheilagh grew and expanded with Madewell, working with them through her B.A., her M.A., and beyond.
“I have always enjoyed the hustle of styling on the sales floor with women, I love it.”
Sheilagh is the type of woman who can wear 4-inch heels while strutting it on the sales floor all day. She has a singular kind of energy. Big Deal Energy.
While Sheilagh naturally loved the retail atmosphere of Madewell, co-workers truly made the place special.
Her co-worker turned mentor, Julie, most stood out to Sheilagh for her ability to make other women use clothing to feel as confident as she herself felt.
“One of my absolute favorite people and mentors I’ve ever had, Julie Miller, she’s the one that hired me, she had that confidence and swagger, and amazing air of ‘I can do anything I set my mind to.’ I looked up to her, and she was a great stylist. I think she found confidence through clothing and so she was always buzzing about the place.”
Even Sheilagh, who loves clothing and is a great stylist herself, looked up to Julie for her passion to dress people in a way they love. It just helps to have your enthusiasm reinforced by those around you!
Julie gave the gift of Clothing Confidence to the women she styled at Madewell.
“One of the biggest joys that [Julie] seemed to have was making other women feel confident. Women would come in and say ‘I’m nervous. I have a date later. I don’t know what the heck I’m going to wear,’ and we would come together and look at new arrivals and how their body worked and how they wanted to come across on the date, and it was all these questions. It was a much more personalized styling experience than your average store.”
Madewell took the model of Neiman Marcus and treated each customer as they would a high-dollar shopper. This is no Abrecrombie & Fitch where someone will chuck a pair of jeans in your face upon entering the store.
Madewell offered a world of personalization and connection that made Sheilagh happy to be at work.
… and it’s what made Sheilagh so successful. She ended up being one of the top salespeople and was responsible for styling training tutorials. HELLO BOSS BABE.
“Everytime I think back to where my roots came from as far as confidence is concerned, it stems from my time at Madewell.”
When Sheilagh started, it was only 5 stores, and by the time she left (after coming back to the stores a few times), there were more like 150 stores. She helped build and mold Madewell to the store we know it as today — how neat is that?
Founding the Naked Lady Society
And it seems retail is too fun to stay away from for long. While Sheilagh’s day job is as a high- power, nonprofit professional, she hasn’t managed to shake off her interest in retail and clothing.
She, with a few other modish ladies, founded the Naked Lady Society in Charleston, South Carolina, a nonprofit focused on creating events that bring women together and allow them to swap clothing for free.
I love this idea for so many reasons.
It allows women of all income brackets to try out new styles, prepare for an upcoming event, or refine their office attire all for free.
When women show up to a Naked Lady Society event, they bring a bag of their own clothing to swap. Some of these women are former ad execs, some have fun 80s cocktail dresses they’ve retired, some have trendy fashions of today that they’re looking to swap for something new.
The style range is as dynamic as the women who show up to these events — and the Naked Lady Society brings in a diverse group.
“There are women who are retired now who don’t need these pencil skirts and they’re throwing them in the pile.”
Let’s say you are re-entering the job force after having a child and need to revamp your wardrobe with some professional-looking clothes. You show up to a Naked Lady Society swap, pick up some gently used tops and tailored jackets, and in turn, you share your old maternity clothes with the next mom-to-be in the community.
This is another reason why I love the Naked Lady Society: it brings women together in a space where they can talk, meet, and socialize.
Not to mention, it helps women figure out what they may need! Sure the crowd-sourced knowledge of the internet is useful, but a good-old-fashioned conversation with other women is a sure-fire way to pick up skills, know-how, and tips for navigating the world. Imagine the helpful conversations going on as women try on different pieces … they’re getting real-time feedback from the other women around them in a supportive, uplifting manner.
Also, it’s environmentally sustainable. Want to try something new? Don’t go to H&M. Go to a clothing swap if you want to look different, or try out a new style.
Women like Sheilagh will be right there with you, offering encouragement. Activities like this help boost Clothing Confidence because they are communal acts. Plus, they’re quick and cost-efficient — you can walk out with a few new outfits in a jiffy.
Sheilagh is the one who will come over and take the belt off of her look and give it to you so that it can complete yours. She wants other women to feel as confident in their looks as she does.
Just as her mentor, Julie, taught her to pass on the gift of Clothing Confidence, Sheilagh keeps the tradition alive through the Naked Lady Society.
Naked Lady Society in COVID
Even though we’re in a time of pandemic, that doesn’t mean clothing ceases to matter or exist.
It still matters.
Connection matters.
And Sheilagh knows this.
That’s why she’s now exploring how to hold events outside. It’s a bummer to me to see an initiative get squashed because of COVID, but Sheilagh remains determined.
Pre-COVID, the Naked Lady Society was blowing up, and I hope it finds its footing again during these psycho times.
Be sure to follow the Naked Lady Society on Instagram @nakedladysociety and Facebook to stay in the know about future swaps, and maybe even discover a swap coming to your city.
Sheilagh’s Top Clothing Confidence Tips
Straight from Sheilagh’s mouth to your brain.
Pretend Your Wardrobe is a Clothing Swap
“I do this periodically and drag out all the things from the depths of my wardrobe and when they are all lying in a heap it's the perfect atmosphere to get creative. “
Real-Time Feedback
“Get feedback from an honest friend or better yet — a stranger. I tend to be pretty good at knowing what I like and what I feel Clothing Confident in. But there have been a few times where good friends and complete strangers have set me straight. When I worked at Madewell one of our sales tactics would be to get shoppers involved in the styling process with each other. When two women would pop out of the fitting room at the same time we’d ask what they thought of their neighbor’s outfit. Complete strangers, it was a fun way for them to get immediate feedback and a confidence boost. And they usually went home with the outfit.”
You don’t need a sales associate to get this convo going! Turn to the lady next to you in the dressing room, let her know how fabulous she looks, and just ask her how that top looks: “Be honest, what do you think about this color on me?” You’ve shared Clothing Confidence, and you’re getting a second set of eyes before the register.
“Now that I am running Naked Lady Society and hosting clothing swaps, I still get to encourage conversations around clothes and open, naked if you will, conversations about styling. Because the clothes are free and it’s an extremely low risk environment, it’s like a creativity bomb where women can flex their own styling muscles. They ask each other questions, they style each other. You’ve heard the saying — women dress for other women. And if that’s the case, it’s good to get some feedback once in a while.”
Capsule Shop
“When swapping I encourage people to go nuts — “grab that item you’d never dream of, it’s FREE,” I always say! But when thrifting, and especially when shopping for new clothes, it helps to shop in a “mini capsule” with items that you can instantly style together. Knowing what will blend well with your existing wardrobe is the ultimate goal, but at least if you know you are bringing home items that can instantly work well together, you’ll be more likely to wear them again and style them more confidently at home.”
Flex Your Artistic Muscles in Other Areas of Your Life
“Two of my style icons happen to be interior designers. Checkout Leanne Ford’s construction chic outfits and Abigail Ahern for her forever comfortable and effortlessly cool fashion choices. These two women are clearly creative when it comes to styling interiors, but I love how it transfers to their discerning clothing choices too.”
Who are the style icons on your Pinterest board? Looking for some fresh inspiration? Take your cues from architecture, films, bygone decades and more:
“I tend to pull inspiration from Irish Manor Houses, dive bars, Japanese prints and textiles, the 1960’s, and anything macabre. I have a deep love for photography, paintings, and I’ve had a great time dabbling in interior design with my own home. Visiting local art museums, attending rock concerts, or even just a quick trip down the rabbit hole that is the Smithsonian American Art Museum website gives me a boost. I find the more inspired I feel the more it shows.”
At Seeking Inspirato we tend to talk about Dynamic Personal Style in terms of clothing, but Sheilagh is so right about this! Style does not end with clothing and jewelry, it extends to walls, textiles, floor coverings. In quarantine, this is more important than ever. Surround yourself in beautiful environments and beautiful clothes to inspire confidence.
Thank you, Sheilagh!