Not The Clothes with Sydney Engelhart

Sydney is a stylist and consultant based in Los Angeles. She’s been working in fashion for over a decade and has helped dress some of the most photographed women in the world. (cc Margot Robbie, Sienna Miller, Hailey Bieber, Michelle Williams, Sofia Richie, Dakota Johnson, Mikey Madison. While I can’t divulge any off the record details, I will say this: all my favorites are exactly how I imagined them to be. And for that, I love them even more.)

I love her work and I have admired her point of view for years.

Reva Luft: Where does your taste come from? Was there a moment it clicked, or did it accumulate over time?

Sydney Engelhart: I’ve had a certain confidence through clothing for as long as I can remember. I was a strong-willed child—very decisive about what I wanted to wear, always noticing details, always putting outfits together. I went to a private school, so I was working within the confines of a uniform, but somehow still managed to get sent to the principal’s office for over-accessorizing. I’m honestly shocked my parents allowed it, but I think they were entertained by my creativity—and I love them for that.

In my teenage years, I really clung to fashion as an escape. A way to feel interesting, mostly to myself. That’s still what I love about it. You might not feel like the smartest, prettiest, or most successful person in the room—but your clothing and personal style hold so much power in how you’re perceived.

I’m a bit shy, a little introverted, and honing my taste has always felt like the clearest way to express myself. Getting dressed elicits a feeling I can’t find anywhere else—and I’ll probably spend my whole life chasing that feeling every morning. When I’m in tune with myself, it can completely shift my day.

RL: Where do you find the most inspiration these days? Pinterest, magazines, real life?

SE: I will never deny my love for Pinterest or a good magazine—but honestly, I feel most energized by people watching. There’s something about seeing someone you don’t know with great personal style. The mystery of it.

It’s probably more obvious in New York or LA, but there are interesting people everywhere—if you’re looking up from your phone and actually paying attention.

I’m also really inspired by my friends. We all have such different personalities and tastes, and there’s always something to take from their thoughtfulness and quietly pocket that away.

RL: You’ve helped dress some of the most photographed dressers over the years. Margot Robbie, Sienna Miller, Michelle Williams , Sofia Richie, Hailey Bieber, Dakota Johnson. Beauty aside, what actually makes someone good at wearing clothes?

SE: I obviously believe in the power of a good stylist—but because I know everything that goes into it, I’m actually more intrigued by the celebrities who dress themselves while being photographed constantly. There’s a realness to it that I admire.

Jennifer Lawrence is such a prime example. Her street style is entirely her own, and it’s incredible—because there’s a fearlessness to it that jumps out at you in photos. Not everyone has that. You can tell she genuinely loves fashion, and because of that, she can own whatever she’s wearing that day.

RL: This actually made me do a full 180. I always assumed Jennifer Lawrence had a stylist behind all her street style looks, and honestly, because she’s photographed so much, her style started to feel almost performative to me. But, now Sydney has completely changed my mind. And now, I think Jennifer Lawrence has amazing style. This is exactly why I love having people like Sydney in my orbit. To challenge (or in this instance, correct!) the way I see things.

RL: What does wearing something with confidence look like to you?

SE: I think confidence starts internally—it’s the quiet certainty of genuinely liking who you are and believing you’re someone worthy of good things. But it reveals itself outwardly, almost immediately, in how you show up. In what you wear.

There’s a kind of ease to it—dressing for yourself, trusting your instincts, knowing you can pull off whatever you love simply because you love it. Not shrinking, not overthinking, not asking for permission. These are the types of people that I notice almost immediately before even exchanging words. Just an openness to being seen, and maybe even a willingness to be a little more interesting than expected.

RL: When it’s not a red carpet. A trip, a dinner, just life. How collaborative is the celebrity stylist relationship? Who’s actually making the decisions?

SE: It really varies. Some clients hand over the reins completely, others are deeply involved and have strong opinions. Some stylists only do red carpet, others are involved in everything—daily dressing, travel, dinners. The constant is fittings—that’s usually where the client chimes in. Personally, I find it most fun when the client loves fashion and wants to be involved. The more collaborative it is, the more rewarding it becomes.

RL: There’s a difference between flattering and good style. In your world of celebrity dressing, which one wins?

SE: This is such a classic tension in fashion. So many runway looks are stunning works of art—but can be incredibly unflattering.

It’s probably why a lot of the “hot girls” in Hollywood lean toward custom—it guarantees both.

But I actually have so much respect for the women who choose the fashion statement over the flattering option. You don’t have to be “hot” every night. Fashion is fashion!!!!!!

RL: What’s the last thing you bought for yourself? Did you know you wanted it right away, or did it grow on you?

SE: A pair of Prada Spring 2013 silk shorts I found on The RealReal. They are black with white flowers. I highly encourage anyone who isn’t familiar with that collection to go through it— it’s my favorite. The flowers add a hint a “weird” that I’m always leaning towards.

I’m also very committed to refreshing my bras and underwear drawer every year. I’m a bit of a Cuup fanatic—I swear by everything they make.

RL: I am definitely doing a Cuup deep dive after this and putting in an order.

RL: You just landed after a 12 hour flight and have an hour before lunch. What are you putting on?

SE: Layering, always. A white t-shirt (usually this one from Aritzia), a button-up (this by 6397 or this from Auralee), a great trouser (the Aflalo Surf pants—you had them first and sold me), and flip flops (A. Emery) like the LA girl I’ve become.

A diamond earring (Dorsey) to feel a bit put together, a low messy bun to match my exhaustion, and sunglasses—non-negotiable. They’re my security blanket. Either the Jack from Thistles or Oliver Peoples Davri.

And my Row backpack I bought a few years ago (one here on TRR). I’m so selective with The Row, and after buying this, I genuinely feel like I could never buy anything else from them again. It’s that good.

RL: There is nothing more flattering than inspiring your style heroes. My Aflalo surf pants are one of my favorites.

RL: What will we never see you wearing?

SE: Capris, oversized shorts, square toe-shoes, cropped blazers. Not for any other reason than I just don’t love it on myself.

RL: I'm going to LA in a few weeks. I might try to change her mind on the oversized shorts.

RL: The eternal conundrum every woman faces. What’s a recent outfit you wore to dinner?

SE: This is the eternal conundrum—even I struggle with it, especially for a date.

I almost always land on a fitted longsleeve, a great trouser, a boot or heel, and a leather jacket. The jacket grounds everything—especially if the outfit leans slightly sexier. My style is more boyish, so it balances things out.

Dinner is also when I bring out whatever tiny vintage bag I’m obsessed with at the moment. Completely impractical, but perfect for night.

RL: Would you rather be slightly overdressed or slightly underdressed?

SE: Overdressed, always.

LA is so casual—it makes me a little sad—but I’ve accepted that I’m usually the most overdressed person in the room. And honestly, I like that. It makes me feel special.

RL: Whose style do you always find yourself going back to?

SE: Miuccia Prada, Annabelle Dexter-Jones, Alexa Chung, Leandra Medine, Jennifer Lawrence, Alex Eagle, Penelope Cruz.

I love staying inspired by women at every age and stage—there’s so much to learn. For men’s style, I’m always in awe of Aaron Levine.

RL: What’s your favorite ‘fashion rule’ to break?

SE: That petite people shouldn’t wear oversized clothing. It’s all I want to wear—and life is short!!!!

RL: From a fellow short girl, amen sister

RL: What’s one thing people overthink when getting dressed?

SE: That it matters. That’s the best part about fashion—it’s entirely up to your own interpretation. No one is thinking about you, and if they are, it’s probably “oh she’s so cool.”

So don’t overthink it. Wear what you love, take it for a spin, and pay attention to how it makes you feel.

RL: “That it matters.” Honestly, one of the greatest answers to this question that I have ever heard.

RL: What’s one thing they underestimate?

SE: A good outfit is simply an outfit you love.

The emotional response it creates can change your entire day—it can shape your mood, your energy, even the music you listen to or what you order for lunch. It gives you confidence. It makes you say hi to a stranger. It makes you want to do more, be more.

Fashion people are chasing a feeling. Always.

Any pieces Sydney mentions throughout this interview are linked with her affiliate links.

xx

Reva

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