CJ Greenhill Caldera

Curatorial assistant, Hirshhorn Museum and Sculpture Garden

The Look

“This Valentino dress, which I found at an estate sale, is one of my favorite pieces. The graphic piecework reminds me of the work of Cuban concrete artist Loló Soldevilla and the geometric experimentation of Brazilian artist Lygia Pape. I love when fashion echoes the visual language of artists I admire. My Chanel Mary Janes, from the consignment shop Inga’s Once Is Not Enough, are workhorses: elegant enough for dinner but comfortable enough to glide from gallery to gallery.” The bag is by Lulu Guinness, brooch by Giorgio Armani, sunglasses by Loewe.

Style Tip

“Patterns and prints are meant to be mixed, and color is everything.”

Outfit Staple

“My Pomellato ring stack. Each ring came from a different woman in my family, allowing me to carry their love and strength with me.”

Feels Best Wearing

“An Alice + Olivia bomber jacket I painted with DC monuments, cherry blossoms, and museums.”

Oldest Thing in Her Closet

“A jacket made from Guatemalan huipils [embroidered tunics], gifted by my Mami, who acquired it while covering civil wars in Central America in the 1980s.”

Steven M. Cummings

Documentarian and photographer

The Look

“What makes this outfit work is the combination of things that shouldn’t go together but actually do, from the antique bowler hat to the Red Wing boots. I found the vintage button covers in an antiques shop.”

Style Philosophy

“Function with style. I dress in a way that is both work and play.”

Oldest Thing in His Closet

“The 1800s bowler hat by Abercrombie & Fitch. I found it in an antiques shop in Baltimore. The impact it has had on my look is iconic.”

Most Complimented-On Accessory

“A plaid rain jacket from Ralph Lauren. I knew it was a masterpiece when I bought it.”

Go-To Shopping

“Thrift stores. The small ones usually have the best quality, and the big ones you never know what you are going to find. The surprises you do find are what separate you from everybody else.”

Latest Splurge

“A hundred-year-old work jacket that has many patches and repairs. It reminds me of the quality of old clothes and how hard people worked in them. I found it at a vintage store in an alley off Georgia Avenue called Dr. K. You don’t need a password to get in, but you need to have an invitation to shop there.”

Leo Tucker

Managing partner, Northwestern Mutual

The Look

“My cardigan is by East Side Golf. It’s minority-owned and brings an urban flair to golf—they push authenticity and uniqueness in a game that’s more ‘uniform’-driven. I like to support this company because they’re a small creative. And I always get compliments on my eyewear.” These glasses are by Maybach.

Style Philosophy

“You’re not properly dressed unless you’re taking a risk. Otherwise, you’re wearing a uniform.”

Style Icons

Cary Grant and Brad Pitt. Grant was “meticulous about everything he put on, no matter the occasion.” Pitt’s style “has evolved over time and is always age-appropriate and chic.”

Outfit Staple

“Custom navy blazer—emphasis on custom. It works in every occasion—work, travel, the country club, and casual nights out.”

Favorite Occasion to Dress For

“I love a black-tie event. Even though everyone is dressed almost the same, you have the opportunity to stand out with the right pocket square, tie, or shoes.”

Go-To Shopping

Paul Stewart, Ralph Lauren, and Brunello Cucinelli. “They all have timeless pieces that endure.”

Latest Splurge

“Ralph Lauren cowboy boots. I bought a few pairs in different colors—they’re that great!”

Brittany Carlson

Co-owner, Lulu’s Winegarden; hospitality publicist and CEO, Julep Public Relations

The Look

“I’ve been embracing polka dots—they feel both playful and timeless. I’m also a fan of the comfort of AFRM’s mesh designs. The skirt is fitted, but I love how it flares out a bit at the bottom—it’s super-flattering. The jewelry is all about sentimentality: bracelets from my wedding, bracelets engraved with messages from my daughters, and a vintage gold bracelet my grandmother passed down to me. The Cult Gaia bag featuring sculptural gold-swirl hardware is the perfect statement accessory.” The shoes are by Stuart Weitzman.

Style Philosophy

“Comfort first, but make it chic and add a pop of fun. My style lives somewhere between ‘cool mom chasing kids’ and ‘meeting friends for drinks in 20 minutes.’ ”

Style Tip

“If you’re looking to play around with your style, I’m big into Nuuly. It’s a fun, low-stakes way to experiment with trends. I love a sustainable closet!”

Outfit Staple

“A matching set. They make me feel instantly put-together, with such low effort.”

Oldest Things in her closet

“My grandpa’s cowboy hat and my mom’s vintage Coach bag.”

Latest Splurge

“A fall fur-cuffed brown jacket from this cool Scandinavian brand, Baum und Pferdgarten. I’m into browns and warm neutrals this season.”

Dawn Crothers

President and creative director, Something Vintage Rentals and ColorHouse Design

The Look

“I love this L’Ideé outfit for its movement and details, from the ruffled top to the pleated skirt. I paired the icy-blue dress with orange opera gloves from Amazon, shoes by Kat Maconie, and a necklace by Loren Hope for the perfect contrast of color.”

Style Philosophy

“I’m a maximalist at heart and hunt for colorful signature pieces that have a little extra flair and detailing—two-toned jeans, fringe accents, embroidery, puff sleeves. I love mixing bold, contrasting colors with patterns and prints. I’m a fan of using shoes and hats as pops of color, and I love a good pair of statement sunglasses.”

Feels Best Wearing

“You’ll normally find me in a statement T-shirt—I collect ones from the ’70s and ’80s. My favorites are band T-shirts—and a bright trucker hat.”

Favorite Occasion to Dress For

“I love an event with a themed mood board. Give me the vibe and I will go all out.”

Go-To Shopping

“Vintage Vintage Vintage in Union Market. It’s a great place to find unique pieces and a well-curated collection.”

R. Lucia Riddle

Certified wellness and fitness coach, Sister Strength; retired financial-services executive

The Look

“This ensemble is by my friend, Nigerian designer Patience Torlowei, who has had her work in the National Museum of African Art. One of the caftans she designed for André Leon Talley was on display in the Metropolitan Museum of Art’s ‘Superfine’ exhibit.”

Style Icons

“I have three. My first was my mother. I loved to watch her dress for club meetings and parties. She had such flair and knew she was the most beautiful woman in the room. Second is a cross between Lena Horne and Diahann Carroll—beautiful, poised ladies with great, classic style. On a current level, Lupita Nyong’o always seems to get it just right.”

Style Tip

“Find that signature something with which you can be associated. Mine is some sort of pin or brooch on my left shoulder—most often a flower or a porcelain creature pin by Cynthia Chuang.”

Feels Best Wearing

“Interesting earrings. With my close-cropped hair, I can let earrings be a focal point.”

Oldest Thing in Her Closet

“A 30-plus-year-old black leather St. John box purse. It’s my go-to for making any outfit just a little dressier.”

Latest Splurge

“A summer hat from Lock and Co. Hatters—a shop on my itinerary whenever I’m in London.”

William Goodman

Senior digital-marketing manager, MDG; freelance writer, GQ, Men’s Health, TheWrap, and InsideHook

The Look

“The striped oxford is by Wythe New York—shout-out for being one of the few retailers to offer oxfords in tall sizes—and then the Merz b. Schwanen half-zip over it; the wider collar gives it character. I try to match my jacket and shoes: The Solovair x Noah tassel loafers pair well with the vintage-inspired Billy Reid shearling leather jacket. My dad, who passed away, had quite a few pairs of tassel loafers, so I like wearing them. But also, this pair has that Doc Martens–style lug sole, which gives it the right amount of attitude.”

Style Philosophy

“Buy better, buy less.”

Style Tip

“Play around with textures. It’s a simple thing to do that can stand out, especially if you’re a little tepid about bold patterns or colors.”

Outfit Staple

“Sweaters. I cannot get enough.”

Feels Best Wearing

“I enjoy dressing a sport coat up or down. I’ve worn double-breasted jackets with a great graphic tee to parties or with an oxford to a nice dinner—they’re so versatile.”

Latest Splurge

“I got a Cowichan sweater—that’s the style of knit Ryan Gosling wears in Project Hail Mary —with mallard ducks on it that was more than I wanted to pay for a vintage knit. But it looks so great that I couldn’t resist.”

Symone Sanders Townsend

Anchor, MS NOW

The Look

“I am the queen of belting a dress. My team jokes that I think every outfit needs one. I’ve had this belt—maybe an old Zara find—for years, and it instantly gives shape. The dress is thrifted. I love mix-ing vintage finds with pieces I’ve collected over time. The whole outfit gives vintage newswoman in the best way: classic, confident, and unmistakably me.”

Style Philosophy

“Power with intention. I’m drawn to pieces that feel polished, structured, feminine, and commanding all at once.”

Outfit Staple

“A great blazer with a strong shoulder. It instantly sharpens any look and makes me feel ready for whatever the day brings.”

Feels Best Wearing

“Leggings, a headscarf, and absolutely no pressure to be anywhere.”

Oldest Thing in Her Closet

“My mother’s trunk from the mid-1970s. She traveled around Europe with it, and now it holds my purses. It’s one of my favorite pieces because it carries both history and style.”

Latest Splurge

“Makeup. Have you seen the price of beauty products lately? I’m blaming the tariffs and choosing not to do the math.”