I Thought I Had Good Style—Then I Hired a Stylist
What happened when I finally asked for help with my closet.
I’ve been getting more compliments on my style recently, and here’s the truth:
I haven’t been doing this alone.
This past year has been all about trusting the people around me to help bring my vision to life—whether it’s Elaine becoming our CEO or bringing on Dani as our Creative Director, I’ve learned that elevating anything (a business, a wardrobe, a creative vision) requires authentic trust and collaboration when you bring on incredible talent. And now, finally, I brought that same philosophy into my personal style—I hired a stylist.
But let me take a few steps back.
If you’ve followed my journey here or through Crown Affair, you probably already know this: I love collecting beautiful things. From art to fashion to small objects with soul, I’ve always found joy in surrounding myself with intentional beauty. I thought I had built a wardrobe I was proud of—and I have. But I also knew something was missing.
Like so many of us, what I was lacking wasn’t necessarily taste or appreciation for fashion. It was what I call the touch.
What is the touch you ask?
The touch is that intangible magic some people just have when it comes to looking cool. It’s an innate ability to assemble pieces with effortless intention. Think of it like a prima ballerina—her movements look so natural, so unforced, that you forget how much training went into them. That’s what the touch feels like. It’s not just about the clothes—it’s how they’re worn, and that takes extraordinary creativity, practice, and time to play.
I have a few close friends in my life who have the touch.
The first person who comes to mind is Juliana Salazar. She just has it. It’s always in the little details: the way a necklace sits, how a sock hits at the perfect height with an unexpected shoe, or how she layers something classic in a way you’ve never seen before. There’s a reason she’s styled (and art directed) so many of our early Crown Affair shoots—and most recently, she styled and stars in the newest campaign we just launched with Eliou.
That brings me to Cristy and Duda from Éliou—who I first met through Juliana when I moved to Miami four years ago, which makes our collaboration and campaign feel all the more special. They always look put together in the most playful and effortless way. Another friend who absolutely has the touch? Nikki, the genius behind Kule. Whether it’s a beach day or a formal event, she always shows up in a look that’s been thoughtfully assembled—pieces she’s been collecting with intention over time, styled in a way only she can.
For all of these people, it’s never just about the clothing—it’s about how they put it all together. I’ve always admired that ability from afar, but never quite had it myself. Their ineffable sense of composition made me realize that even though I love to shop, I often wasn’t seeing beyond the item. I was collecting, not composing. I wasn’t thinking about how the shapes, textures, layers, and silhouettes come together to tell a story.
The disconnect I’d long felt with styling my pieces suddenly came into focus when I met Kelly Klein.
Kelly and I met two years ago at a mutual friend’s unforgettable 34th birthday—imagine 14 inspiring women on a yacht for 10 days, endless vintage Dom Pérignon, a fully stocked arts and crafts table, and nonstop laughter. It was as epic as it sounds. The moment Kelly boarded, I was in awe. She had the touch. The way she layered her jewelry, tucked in her tees, scrunched her sleeves—it was all so effortless and seemingly hard to replicate. Even if I bought the same exact pieces, they never came together quite like hers. Kelly had spent years as Head of Merchandising at Veronica Beard, and now lives in Miami with her family as a Creative Consultant and Personal Stylist, taking on special projects and styling clients.
Even though I met Kelly two years ago, it wasn’t until recently that I felt ready to bring her into my space, go through my closet, and truly collaborate on looks.
The truth is—I was a little scared. Styling and shopping are incredibly personal and emotional experiences. Our physical stuff can carry weight, memories, expectations, and often, it forces us to confront things we’re not quite ready to process (hence, the empire Marie Kondo built). But I knew it was time to trust someone with a clear eye and a kind heart to tell me what was working—and what could be better.
Some context: before working with Kelly, I did two virtual sessions with the incredible Allison Bornstein, the creator of the Three Word Method™, her book Wear It Well, and newsletter. Those sessions were not only so fun (I adore her) but they were extremely helpful. They helped me understand the foundations of my style, identify the silhouettes I naturally gravitate toward, and, most importantly, define the three words that guide how I want to feel in my clothes.
We landed on:
Whimsical
Classic(al)
Minimal / Effortless
Whimsical felt like an obvious choice when looking at my wardrobe—it captured my love of collecting joyful pieces, like a pair of Loewe Crown Affair Green rhinestone heels or a Chanel splatter-paint bag from 2015. But as I’d later realize working with Kelly, this word reflected my habit of collecting, not composing. The pieces were there, but they weren’t speaking the same language.
Classic(al) made sense too. It reflects my mostly neutral palette and my pull toward timeless silhouettes—jeans and a tee, a blazer, generally more masculine separates balanced by softer, feminine tailoring (think the Attersee Sculpted vests I wear often).
The trickiest word(s) was Minimal / Effortless. At first, we landed on Minimal as my “balance” word— for example, if I picked a whimsical dress, Allison would encourage me to anchor it with something simple, like a an elegant Emme Parsons slide. But the word I really wanted was Effortless. That was the aspiration. And the truth is, it would be hard to unlock effortless through FaceTime alone. It takes hours of playing, experimenting, and trying things on in real life to understand how that energy shows up in your wardrobe.
Enter: Kelly styling sessions, IRL.
We’ve done two 5-hour sessions together so far, and somehow they feel like 30 minutes. The first one was focused on an upcoming work trip, and we honed in on styling pants and button-downs. I probably own more pants than anything else, but I wasn’t clear on which fits were working and why. That’s when I learned about the J-stitch (which is the stitch pattern used in constructing the fly on a pair of pants/jeans — pro tip: look for a longer J-stitch—it's why these Khaite pants look so good).
The other big unlock from that first session? Bags—and the lack of slouchy ones in my wardrobe that could bring more ease to a look. And even bigger: a philosophical shift. I started seeing clothes differently. It honestly changed the way I even look at styling Pinterest boards now — I finally started seeing shapes instead of just the items.
In our second session a few weeks later (and yes, in the time between, I was living in the looks she styled—when I didn’t, I didn’t feel quite as cool), we hit the ground running. This time, we focused on packing for my upcoming trip to Japan, building out daily looks that felt like me and could be worn multiple ways. Rewearing, reimagining, remixing—it was all about versatility, without sacrificing vibe.
A few things I’ve learned so far from working with Kelly:
A look needs balance.
Before working with her, I’d often reach for too many “pieces” at once—a structured top-handle bag, a bold shoe, something clearly designer—and it all competed. Now? I’ve learned to soften the overall vibe. Pair the statement barrel pants with a slouchy suede bag. Swap the predictable black ballet flat for a Birkenstock clog, or pair a low-key sandal with a formal trouser (something I never did before!). It’s not about toning it down—it’s about creating harmony.Anything can be a skirt.
This tip was the big shift for me in understanding the sections of a look. For my proportions, wrapping a shirt or layering a longer top around the waist adds dimension and structure. A button-down tied just right can completely shift the shape of a look. I almost gave up on a beautiful fringe top from Attersee (similar here) because I thought it was too boxy and hit the wrong spot on my arm, but layered under my favorite off-the-shoulder denim jacket, it’s become something I actually reach for often now. The fringe is a skirt.Speaking of… dresses can be skirts.
I’ve always loved dresses, but I don’t get enough wear out of them. Kelly taught me to treat them as versatile layering pieces. For example, there’s a Cecilie Bahnsen dress I love but don’t get enough wear out of because I felt like I could only wear it for an event. Kelly layered it with a long-sleeve striped tee and fitted knits, giving the dress a whole new life beyond an event look.And button-downs? They can be anything.
Tied at the waist. Worn off the shoulder. Tucked strategically to look tailored. Or even layered under a jacket as a pseudo-skirt moment. Kelly taught me that they’re he secret weapon of the closet. And she has pro moves for rolling the sleeves (make sure it’s above your elbow to lengthen your arm!).Forget where the item is from — it’s all about proportion.
I pulled out a beautiful pair of pants from The Row… and they just weren’t working. The J-stitch was too short, the silhouette was off for my body—and despite the beauty of the item on its own, they didn’t serve me. Kelly helped me let go of pieces like that, no matter how chic or aspirational. It’s not about the brand or the size on the tag. It’s about how a garment moves with you, falls on your body, and fits into your life. The piece she played with the most in our looks for our last session? A striped long-sleeve shirt from Gap that I thrifted for $5 my freshman year of college in 2009. I’m honestly shocked I still have it and grateful I never let go of it.When in doubt, add some slouch and suede.
This was a surprising one. I used to avoid suede in Miami (and gravitated toward structure with accessories), but bringing in something softer—whether it’s a slouchy bag, a belt, or a loafer—grounds the outfit. Adds texture. Makes it feel lived in, not too precious. Just right.
(For more epic guidance from Kelly, subscribe to her newsletter :)
This whole process reminds me of one of my favorite childhood books, Math Curse, by Jon Scieszka, who also wrote The Stinky Cheese Man and Other Fairly Stupid Tales IYK,YK).
Math Curse is about a girl who suddenly sees math problems everywhere—and she can’t unsee them. That’s how styling has started to feel for me. I’m no longer just looking at individual pieces; I’m seeing shapes, colors, proportions—how everything works together. It’s unfamiliar, but exciting.
All this to say—working with a stylist has been one of the best decisions I’ve made this past year. It’s completely shifted how I shop and consume. While it takes some creative energy upfront, it’s made getting dressed effortless—having go-to looks and formulas makes all the difference. It’s a rhythm I know well from haircare: invest in the care early on, and everything gets easier (and better) from there.
I still have a long journey ahead, but I feel more confident in how my clothes fit, move, and express who I am, which is important for someone who lives a very outward-facing life.
Beyond the styling, Kelly said something that really stuck with me and is probably more profound than she even knew:
“It’s about having the confidence to not need the label.”
Styling my looks isn’t just the work; that’s the real work. And I’m down to do it.
If you’re nervous about hiring a stylist, I get it. It can feel overwhelming. But when you’re ready, think of it as an investment in yourself, like working with a great acupuncturist, coach, or chiropractor. It’s a skill that helps keep a very personal part of your life in tune. It’s something that’s going to make you feel your most you.
For me, it meant surrendering to the fact that I needed help, and admitting I’d spent a long time living in the fantasy side of consumption—collecting pieces without really reflecting on how they work together. Exploring the 'effortless' part of my style has been exciting, a little scary, and unfamiliar… which, of course, means it’s where the real effort (and magic) lives.
And while I may not have the touch in my DNA, I’m more than willing to put in the time to figure out how I want to show up without constantly needing something new. Sometimes the best pieces aren’t new at all—they’re just waiting to be seen with fresh eyes.
I hope sharing this journey has been helpful—or at the very least, sparked something for you.
I’d love to know how you’ve been thinking or feeling about your own wardrobe lately, or if you have any questions for Kelly or Allison and the work they do.
Take care, and take your time, always,
Dianna
And now… Three Things I Love and A Haircare Tip:
Dianna’s Signature Air Dry Collection My holy grails for mastering the art of the air dry. After two recent tropical getaways, I can confidently say: this is all I need for dream no-makeup makeup hair out of the shower. Simple, effortless, and works every time.
Exuma Hat This has become my go-to hat for beach holidays and Miami weekends alike. The wire brim lets you shape it just right, and the inner band with a tie makes it easy to adjust. It works with any look and packs easily for flights as it isn’t too precious.
Pre-Alcohol Z BioticIf you're 30+, take this before a night out. It tastes like electrolytes and makes you feel like you didn’t even drink the next day. Alex and I have been using it the last year and it truly works.
A Haircare Tip: A Seasonal Reset
Spring Is for Shedding What You Don’t Need, Including Hair Habits
As the seasons shift, so does your hair. Spring is a natural time of renewal—not just for your environment, but for your rituals, too. With more moisture in the air and warmer days ahead, it’s a great moment to reassess what your hair actually needs.
Swap out heavier products for lighter hydration, and lean into air drying to let your natural texture breathe. Brush daily to stimulate your scalp and shed what your hair no longer needs—literally and metaphorically. A seasonal reset doesn’t have to be drastic—it can be as simple as taking a moment to care, consistently. Your hair will thank you for it.
"It’s never just about the clothing—it’s about how they put it all together. I’ve always admired that ability from afar, but never quite had it myself. Their ineffable sense of composition made me realize that even though I love to shop, I often wasn’t seeing beyond the item. I was collecting, not composing. I wasn’t thinking about how the shapes, textures, layers, and silhouettes come together to tell a story."
Diana, you nailed the essence of styling! Well done, and beautifully articulated -- thank you for this!
I love all of this so much! I also recently started investing in having experts (who are also friends) teach me about style and makeup and it’s honestly such a game changer!