Elyse Winter on Style, Success & Second-Time Motherhood: Navigating Growth in Business and Life.
Photo Courtesy Elyse Winter / Photos By Aletiza Photo
To call Elyse Winter a stylist would be missing the point entirely. Yes, she’s the quiet force behind some of the best-dressed women, those whose wardrobes strike that elusive chord between lived-in ease and editorial sharpness, whether they’re in Los Angeles, New York, London, or anywhere in between. But beyond the racks of vintage denim and perfectly worn-in tees, Elyse is, above all, a woman in motion. Based in LA but working with clients across the globe, her reach is as expansive as her eye is intentional.
We spoke with Elyse for the second time, just ahead of the birth of her second child this fall, as she prepares to welcome a son into her growing family. In this season of softness and structure, she’s navigating the surreal, sacred, and sometimes exhausting terrain of pregnancy with the clarity that only comes from having done it once before, and with a boy this time, no less.
In our conversation, Elyse invites us into the ever-shifting rhythms of her life: from mothering while managing fittings, to rethinking postpartum plans with the wisdom earned from round one. She shares the pieces she swears by (hello, vintage Cartier, Elder Statesman cashmere, and Jamie Haller flats), the small rituals that keep her grounded, and why being a working mother doesn’t make her feel divided, it makes her feel whole.
Here, Elyse shares what life really looks like right now: messy, beautiful, a little chaotic, and entirely her own.
By Alice Codford
Alice: You are expecting baby number two. Congratulations! How is your pregnancy the second time around? How are you feeling?
Elyse: Yes! It’s a boy. I’m due in October, literally the same week my daughter was born. I’m so excited to have another member of our family and be a boy mom this time around. Pregnancy for me is really rough, sadly. I’ve been nauseous this whole pregnancy and expect that for the remainder of the time. I’m trying to stay positive and calm, but it’s been really challenging.
How has this second pregnancy felt different? Emotionally, physically, or even spiritually, compared to your first?
Elyse: This time around, I feel a lot more confident and aware of what’s going on. There aren’t any surprises here! I felt the same way physically with my first pregnancy, so I basically knew what to expect. Emotionally, it’s been a battle of ups and downs. I struggle with health anxiety, so being at the doctor constantly for tests and checkups has been something I’m working through. Spiritually, I feel so connected with my son, and it makes my heart melt when my daughter says good morning to my son and kisses my belly.
What are you doing differently this time around, whether in terms of your birth plan, mindset, or the way you’re preparing?
Elyse: This time around, I didn’t hire a doula because I know we’re doing a planned c-section. I’m mentally more prepared for that surgery and less stressed. I’m not fixating on stretch mark creams, hospital bags, and overordering supplies. I feel like I bought so much nonsense last time for myself and the baby that I ended up donating. Less is more?
Are there any lessons from your first postpartum experience that are shaping how you’re approaching things this time?
Elyse: Absolutely. I am planning on pumping this time around. With my daughter, I exclusively breastfed her for a year and a half. I loved that time so much, but I know that given my work schedule and how busy I am, I’m going to balance it by pumping and feeding. I’m also hiring help to support our family, which I was hesitant to do last time. It takes a village to raise a child, and I want to be as present as possible with my children and husband.
Photo Courtesy Elyse Winter / Photos By Aletiza Photo
What has it been like parenting while pregnant? Has your relationship with your daughter shifted in any surprising ways?
Elyse: Ha! My daughter totally is already feeling it. She’s been a lot more needy and clingy with me and wants me to hold her 24/7. It’s going to be interesting to see how she reacts to him at first, especially because they will share the same birthday week. I have a younger brother as well, which makes this whole experience even more special.
What are you most looking forward to about being a mother of two?
Elyse: I just want a mini village. I’m so family-oriented and spend a ton of time with my parents and brother as it is. Making the choice to stay in LA was a really difficult one; however, the benefits of being with my family are so beautiful. I can’t wait to cuddle in bed with everyone, including our dog Crosby, on a Sunday morning. I can’t wait to make pancakes for everyone and just hang out and go on walks. I’m definitely done having kids after this, so the feeling of being complete is one I didn’t think I’d ever feel.
What have been some of your favourite or most meaningful styling projects recently?
Elyse: Oh boy, it’s hard to even pick. I have a client in LA who I’ve become really close to. She and I have a similar style to begin with, which is rare. We go on vintage shopping dates and hang out as friends. It’s been really special growing that relationship with her. I am also working with a client who is battling cancer. Helping her shape her wardrobe and give her pieces to wear for appointments has really been moving for me. I’ve learned so much from her emotionally, and that’s something I’m forever grateful for.
How would you describe your personal style right now? What’s your approach to dressing during pregnancy, especially this time around?
Elyse: I would say I haven’t really changed my style at all this time around. Last pregnancy, I leaned into cosy style and was in sweats every day. This time around, I’m not letting go of my vintage jeans and tees. My style is such a big part of who I am, and I’m not going to push that aside this time. Don’t get me wrong, once I’m wrapped up with appointments for the day, the first thing I do is put on pyjamas!
Photo Courtesy Elyse Winter / Photos By Aletiza Photo
Are there any go-to pieces, textures, or silhouettes you’re loving in this season of your life?
Elyse: I’m loving anything soft and fluffy like Elder Statesman cashmere (yes, even in June). I’m also loving loose linen trousers and t-shirts. I find that balancing my body while getting dressed has been a challenge this time around because my bust has gotten so large. I’m working on it. Playing around with new bra sizes.
What are your go-to outfit formulas right now, especially when you want to feel comfortable but still like you?
Elyse: Jeans, vintage tee, cute flats and tons of jewellery. Nothing has changed!
Is there a current fashion trend you’re just not into right now?
Elyse: I don’t love the Chloe jelly shoes at all. It’s really not for me or my clients.
What 3 outfits should every woman have in her wardrobe? Like, what are your IT looks that are always foolproof?
Elyse: 1. perfect jeans, tee, blazer and kitten heel
2. Oversized knit, leather pant, kitten heel
3. Slip dress, knit, suede knee high boots
What pieces from your first pregnancy or postpartum period have you kept and are using again?
Elyse: Skims bralettes and cotton boy shorts. Freecity sweatpants like it’s 2009 again. I love the nostalgia.
Photo Courtesy Elyse Winter / Photos By Aletiza Photo
Any standout purchases for the new nursery you’re excited about?
Elyse: I’m excited that my kids will have matching cribs. I’m also thrilled that we’re continuing the gingham vibe for this baby as well.
What are some favourite things you’ve bought (or are planning to buy) for baby number two?
Elyse: When I was in NYC recently for work, I stumbled into Bonpoint on Madison and splurged on a cashmere outfit for him. I’m really excited to see him wear it, but I likely will be cleaning it within 2 minutes. Let’s be real! I also love Oso and Me, and got him a few sets I can’t wait for him to wear this winter.
Handbags: What are your favourites right now?
Elyse: Hermes Kelly vintage, Bottega Cabas old school, and The Row backpack I recently brought back out. Lastly, I’ve been reaching for my Balenciaga City a lot because it’s just so easy to throw around.
Shoes: What are your favourites right now?
Elyse: Salomon’s for everyday running around, Manolo Blahnik Carolyne for when I have a work event, Jamie Haller flats for everyday.
Photo Courtesy Elyse Winter / Photos By Aletiza Photo
Jewellery: What are your favourite pieces right now?
Elyse: I recently bought myself a vintage Cartier Panthère watch that I’m loving. I also got another Sherman Field chain that I adore because it’s so long and I can layer with it. Especially since my bust has grown larger, incorporating longer pieces helps a lot to balance my frame. On my wishlist, another locket from Sherman and some fun custom pieces from Fewer Finer in NYC. The owner is an angel, and I’m excited to work more closely with her.
Top beauty and skincare, or makeup products you're loving right now?
Elyse: I’m trying to take care of my skin more this pregnancy. I’m loving the U Beauty eye cream and anything from MBR. I have really sensitive skin, so I have to be careful with what I introduce into the routine.
How has your work as a stylist evolved since becoming a mom, and what’s it like now, navigating work while pregnant with your second?
Elyse: It’s totally shifted for me. It’s a balancing act of support from others and mom guilt. I love what I do SO much, and it’s a big part of who I am. I have to remind myself that when I drop my daughter off with my mom or nanny. My mindset for this pregnancy has been to lay the foundation of my business before he comes. I’m going to take off a month or so in October to bond with the baby and then only take on virtual calls until the new year to heal.
How do you stay inspired in your work while juggling the physical and emotional demands of motherhood?
Elyse: I refuse to change who I am, regardless of the circumstance or situation. What I do for work makes me who I am. I love having both, and being a working mom hopefully inspires my daughter to own her business one day. You have to really believe in yourself and have confidence, and I pray she has that.
Photo Courtesy Elyse Winter
Do you find that your experience as a mother influences the way you approach styling other women?
Elyse: Absolutely. The majority of my clients are women, and a lot of them are mothers. I feel that I can relate to how they feel and what they’re going through. I love working with moms.
What does a typical day look like for you right now? Balancing work, pregnancy, motherhood, and everything else?
Elyse: It’s an absolute shit show. I forget how many weeks I am all of the time! Lol. I have a calendar to keep myself organised, and I have 2 assistants who help keep me in line. My husband and I are OCD, and he helps support balancing it all.
Do you have any hacks or habits that help you manage the creative chaos of running a styling business while parenting?
Elyse: Log everything in your calendar. Give yourself at least 30 minutes a day to have alone time. Remember your worth and charge accordingly.
How do you make space for yourself? How do you treat yourself to self-care time?
Elyse: I’ve been trying to block out 30-1 hour on my calendar each day to take time for myself. It’s become very clear to me that I need to prioritise myself and not bury myself with work. I recently hired a nanny, and that has been life-changing.
What does ‘success’ look like to you in this season - creatively, professionally, and personally?
Elyse: Professionally: Honestly, I’m really hard on myself, and I don’t ever think I’ll feel successful. That drive for perfection and a full calendar keeps me going.
Personally: I want to balance my time more and see my friends. Other than that, I feel inner peace with where my family is at. I’m very grateful.
Creatively: I want to work with some of the larger brands and travel with them.
Photo Courtesy Elyse Winter / Photos By Aletiza Photo
How has your business grown over the last few years?
Elyse: It’s been absolute magic. I work really hard, so I’m not going to sugar coat that. I’m very happy with where I’m at, but again, I’m super hard on myself, so I would be lying if I said it’s enough. It’s never enough. I’m booked now until mid-September and booking some clients for November now. That said, I don’t think I’ll feel comfortable until I’m booked a year out. The mind of someone who owns their own business is wild.
What are you especially looking forward to in these next few months before baby number two arrives?
Elyse: One-on-one time with my daughter Gemma. A trip with my husband. Less chaos - lol!
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