How to be a Stylist with Elyse Winter

Plus her 5 favorite things right now...

Since starting this substack I have been kicking around the idea of doing an interview series. I love interior design, but am always curious about other career paths, especially creative ones. In another life I’d like to try out being a stylist, a photographer, a gallerist, an editor and so on. I think this interview series will scratch that itch, just a little bit, and hopefully give us all some insight into what it looks like to do something different than perhaps our own day-to-day.

Despite working across different fields, there are so many common themes we all share, especially for those of us who are small business owners or do something that relates to aesthetics, whether in the home or fashion sectors.

I am so honored (and it seems apropos given the amount of questions I got on instagram when I casually mentioned using a stylist) to kick things off with one of my favorite people, both the devil and angel on my shoulder when it comes to purchasing new items of clothing, Elyse Winter.

After sharing this, a lot of people asked me why I would work with a stylist, when for my whole life I have had an interest in fashion and a fairly defined sense of style. I tried to think about this in relation to my own business, where many of my clients love interiors, have strong ideas, and still need or want help putting it all together. Fashion is the same in many ways, and I wanted to see what it would feel like to be on the client side for once. I’ve had such a wonderful, creative back and forth with Elyse since we started working together - a fashion reawakening if you will!

Check out her website, follow her on instagram, and finally, read our interview below…!

SL: Tell us about your background - what were you doing before and how did you end up working as a stylist? 

EW: I have worked in the luxury fashion space for over 15 years. I started my career as an intern working for Nordstrom and then worked for Barney’s in personal shopping. RIP Barney’s!!! I spent the last 8 years with Farfetch as a personal shopper and always styled for fun on the side. 

Moving to NYC in 2019 really shifted my world and it organically turned into me building this bicoastal business out slowly. Since then, I have styled a wedding in Vogue, dressed clients for the Oscars, and Met Gala. I would say that my career truly took off after I had my daughter in 2022. I woke up and realized that my passion was helping everyday people get ready and feel good about their day to day lives vs. styling people for special events and red carpets. I personally struggled with finding myself and my style postpartum and I wanted to help others feel their best. Becoming a mother changed me and I wouldn’t have felt the confidence to fully dive into my business if it weren’t for my postpartum experience. 

SL: How do client's typically find you? My business is almost wholly word of mouth - is yours too? Social media? A mix? And how do you get the word out when you're launching a service like this? I had considered sending an e-blast to everyone I knew but then chickened out...

EW: Social media has played a huge role in the success of my business. Even though I have a smaller account, I have gotten 80% of my clients from Instagram. I hate posting videos on Instagram and I refuse to post on TikTok at this point. I totally understand the hesitation to send the e-blast. I’m getting more comfortable with sharing my own personal outfits and life which I think helps resonate with others.

The other 20% is word of mouth and meeting people on the street. I find that my clients like to keep me a secret which is so funny! It’s not embarrassing to use a stylist. Everyone needs a little push. Random, but I recently met one of my repeat clients at J.Crew when I was doing a return for my husband! 

SL: As someone in a similar creative field, but for the home, I always feel like it's our job to listen to and understand a client's personal tastes, but also for them to come at the project with an understanding of YOUR style too, to make sure it's the right fit. Is it the same in fashion? 

EW: Totally. My clients are ALL different. I work with clients who love preppy pieces, edgy pieces, & are all over the map with body types and preferences. I love pushing myself to flex to someone’s personal style that differs from mine. I will say that I always infuse a bit of myself in their looks with my styling influence, not necessarily with the pieces or the overall style themselves. For example, I love denim and I think denim translates into any style to ground a look. All of my clients have great denim. 

Then there are clients who I get personally influenced by.. it’s dangerous. I bought your Lauren Rubinski necklace post closet session when I met you. I was making your most recent edit and I ended up buying the Manolo pictured above as well. Now we’re twinning, but I will style you and I both totally differently in these pieces. 

SL: How do you determine your rates? I know that was one of the hardest parts of going out on my own four years ago and I definitely undervalued my services at first. 

EW: Ha! I absolutely went through that. It’s difficult to put yourself out there and put a value on your personal work. It’s so different when you are negotiating a salary with a company. It was a struggle at first to feel confident in my rates. Now I’ve come to the place where I feel that my prices are justified because I really deliver to all of my clients and I stand behind everything I do. 

I recently had someone reach out to book me and she felt that my rates were too high. Two weeks later she emailed me to book and is now a repeat client! Little things like that really help solidify that I’m worth it. It’s all about self worth. I saw the interior of your house, you’re definitely worth it. Take my money!

SL: Walk us through starting to work with a typical styling client. I know for me, we started with a big closet purge where you helped me decide what to sell vs. donate and then you made some suggestions for filling in... 

EW: I generally like to see someone’s closet so I can pickup on what they’re buying, how they’re shopping, where they’re shopping, and why they’re shopping. It gives me a lot of insight into their buying patterns and what holes we need to fill. I also like to sit down and have a conversation about their lifestyle, insecurities, and goals. I really like digging deep and getting personal with clients. Fashion can be perceived as frivolous, to me it’s so significant in changing how someone feels everyday. I am an open book, so I like to share my own personal insecurities and struggles with clients to help create a safe and open space for them. 

SL: Is it helpful if a client gives you a notable personality for reference when curating their look?

EW: It’s not always necessary, but one of my first questions is… how would you describe your style? Who is your style icon? What brands do you love? Once I have an idea of the direction we’re going in, my job is to fully lean into that direction and also throw them some curve balls that are unexpected. People often have a lot of references they share that may not suit their lifestyle. We work together to nail a balance of what they like, and what actually works for them. 

SL: I recently engaged you to help me curate my cocktail wardrobe for the insane amount of 40th birthday parties I have this year. How did you approach this specific task vs. our first round of edits? I assume it helps that you now have an understanding of my closet. Do you suggest doing a closet clean out FIRST before taking on something more specific like this?

EW: It’s very helpful if I already have had a peak into someone’s closet and world. If I have seen their home or closet I can identify the holes they have to make sure I’m not suggesting something redundant. 

With that being said, I do a ton of a la carte occasion work with clients who I haven’t worked with before. In those cases, I ask a TON of questions to dig deep and understand their style as well as what they really want to feel like. I don’t dress people for where they’re going… I dress them for how they want to feel. To me dressing for a location is costume dressing. My main focus is to ensure a client feels like themselves regardless of where they go. 

For your edit specifically, I focused on finding unique pieces that you wouldn’t have gone for yourself. After meeting with you and doing our initial edit, I have a picture in my head of your current closet and I have your sizing in my notes. I know you enjoy special things that are well-made and feel timeless. I like pushing you out of your comfort zone. I think when you really lean in to your eclectic style you’re most happy with the look. You have great taste to begin with, you just need a little push to take the risk. 

SL: Okay, as a fellow mom, how do you navigate all the traveling back and forth from NY to LA? Any comments on work / life balance? I struggle with this so much! All tips welcome.

EW: Oy! This is my biggest challenge. I have mom guilt all of the time. I didn’t hire help for the first 2 years of my daughters life, it’s been a lot to juggle to say the least. I’m not cut out to be a stay at home mom and my respect for moms that do that full time is beyond words. Balancing work and being a mom/ wife/ sister/ friend is tough. Something always falls through the cracks, which is usually taking care of myself. It’s something I’m trying to prioritize because if my cup isn’t filled I can’t help anyone. When I travel or work with a client I’m fully focused on the job and shut off my mom brain. I really love what I do with all of my heart so it doesn’t feel like work. I look at it as my time “off” as a mom. 

My parents are my rocks and they help with the baby when my husband and I are working. Without them my business would be nonexistent! Shoutout to Sheryl and Richard!

My best piece of advice is to lean on family and remember that what you’re building is not just for you, it’s to show your children an amazing example of a strong business woman is! 

SL: Speaking of travel, can you give us an insider look into fashion week (for those of us who don't get invited and have FOMO? Def not me, lol. 

EW: I have a love/ hate relationship with fashion week. Don’t get me wrong, attending shows and showrooms is a huge perk of what I do. What I don’t love about it is the snobby energy *some* attendees have. Fashion is fun and I find it silly when people act like that. I do love visiting showrooms and learning about new brands. My favorite event I attended this past season was the Ralph Lauren show in the Hamptons. There were horses, vintage cars, & a stunning bar with polo bar snacks. Ralph does an amazing job of transporting you to a magical place.  

SL: What's next for Styled x Elyse?!

EW: International styling! I just landed my first UK client this week. I’m really looking forward to expanding my business and working with people all over the world. I’m so thankful for the ability to work virtually. 

SL: Where do you see your business in 5 years, 10 years?

EW: My goal is to continue to grow my client base and work with repeat clients. It’s such a compliment when a client reaches out to work with me again. I want to take on some new partnerships with brands and eventually would love to exclusively partner with a retailer. I’m currently working with MyTheresa, which is so exciting. I really want to attend Paris fashion week. I LOVE Paris and I secretly speak (broken) French. 

This may sound dorky, but I’m focusing day by day and not so much on the future. It’s the only way I can give my clients and family my attention. Day by day! 

SL: 5 things you’re loving right now, go!

EW:

1. Olivia Von Halle recently sent me this piece and I can’t stop wearing it. It instantly makes me feel chic when I’m home. One of my mantras is that you should always feel good at all times. Pilates, at home, running out for coffee. It all matters! 

2. I am dying for this pendant. Danielle Sherman is so talented and lovely. I went to her showroom a few months back and I want everything she makes. Her pieces are so unique and have such a vintage feel. 

3. Anyone who is my client knows this is my favorite shoe ever made. Black suede, size .5 up! I walked 5 miles in NYC in these and was totally fine. 

4. My favorite brand is The Row. No secret here. I love this button down. I sized up to a Large for a more dramatic look. 

5. Frances de Lourdes makes the softest most luxe tshirts ever. I have a few in my personal collection and call them “night tshirts”. 

THANK YOU THANK YOU THANK YOU to Elyse for sharing your wealth of knowledge and insights with the Intel crew!

Friends, is there anyone you know that you think would be perfect for this series? If so, drop me a note!

x

SL