Kelly Wearstler
Photo by: Hunter Abrams
Party season is here, and with it comes the challenge of deciding what to wear. Let Dress Code guide you on when and where to wear certain outfits and how to style them, with advice from those whose natural style always inspires.
Kelly Wearstler’s outfits, whether for morning, afternoon, or evening, reflect her design work: thought-provoking, dynamic, and endlessly creative. Her looks are never accidental. She strategically mixes textures and favors bold silhouettes that stand out and make a statement. Recently, while hosting a poolside party to launch her experimental gallery and digital platform, Side Hustle, we asked her about her thought process when getting ready for an event.
What’s your process for getting dressed? Do you make an effort even when you don’t have to go anywhere?
I get dressed quickly in the morning after my workout and spending time with my son, Crosby. I dress based on my mood and energy. Some days the outfit works better than others, but once I’m dressed, I don’t change. Whether in denim or a suit, I want to feel inspired. My style is always evolving with me.
When you want to feel confident, what does your outfit need to have?
I choose pieces that make a statement. I’m drawn to structured and textured items and love combining sharp and soft elements. A complete outfit should feel balanced, sculptural, and true to my aesthetic.
If you have a breakfast event tomorrow, what’s a reliable outfit to feel polished in the morning?
Something with presence—structure, texture, and tension. I love a wide shoulder for power and proportion. When it feels sculptural and balanced, that’s perfect.
Is there a dress code that makes you uncomfortable? How do you handle it?
None! A dress code is like a creative brief—it’s a chance to experiment and bend the rules.
How do you approach putting together a look for a luncheon?
I’d go for unexpected material pairings or a statement piece that challenges daytime dressing norms. For lunch, I’d choose something playful and unconventional, like a mini skirt with flats or a vintage t-shirt with platforms.
What are your thoughts on costume parties? Do you go all-in with DIY or politely decline?
I’m all in. Halloween is high-concept dressing, and DIY is where the magic happens.
How do you energize yourself when transitioning from day to night for a dinner party during the 5 p.m. slump?
Music shifts my mood instantly. My playlists are beautifully chaotic—Tame Impala, Massive Attack, Kendrick, Glass Animals, Jamie xx. I love surprises, so the music is always changing, never repetitive.
Kelly Wearstler
Photo by: Eseniia Araslanova
If you have no time to think about an outfit for an after-work gathering, what’s your go-to formula?
Every day in the studio, I experiment with new looks. I’m always ready and want to feel inspired. Any outfit I wear can be transformed with a change of shoes or a jacket.
What’s your take on cocktail attire? Is there an outfit you tend to repeat?
Cocktail attire is a great opportunity to play with proportions and push boundaries with materials and silhouettes. I prefer not to play it safe and usually try something new.
What about black tie? Do you take risks or play it safe?
I’d rather take a risk than blend in. I enjoy pushing proportions and experimenting with curation and form.Which after-dark piece gets the most wear in your wardrobe, year after year?
My bone-colored vintage Chanel bag with small charms that I found in Paris.
—Kelly Wearstler
Photo by: Eseniia Araslanova
Do you have a favorite party-ready piece or accessory that always sparks conversation with strangers?
I love a bow, especially when it’s given a twist. Something oversized or with a bold print adds a bit of edge, balancing strength and femininity. It’s a classic motif, but when reimagined, it becomes sculptural and powerful. Recently, I took a Bode hair bow and wore it as a tie with a full, flowing skirt—it looked super cool. I love when pieces are reinvented and begin to tell a new story.
What’s in your evening bag?
Lipstick, always.
Frequently Asked Questions
Of course Here is a list of FAQs about how Kelly Wearstler selects party outfits that share a narrative with clear and concise answers
BeginnerLevel Questions
1 What does it mean for an outfit to share a narrative
It means your clothing tells a story or conveys a specific mood theme or idea rather than just being a collection of separate items Its about creating a cohesive and expressive look
2 Why is telling a story with an outfit important to Kelly Wearstler
For Kelly fashion is an extension of interior design Its another creative medium to express a point of view evoke emotion and make a memorable personal statement
3 Where should I start if I want to try this
Start with a single piece that inspires youa vintage jacket a piece of bold jewelry or a fabric with an interesting texture Build your story around that one hero item
4 Do I need to buy all new clothes to do this
Not at all The best narratives often come from creatively mixing what you already own with one or two special intentional pieces
5 Isnt this style too costumey for a regular party
The goal is artistic expression not a literal costume The narrative is subtle and sophisticated achieved through color texture and silhouette not props
Advanced Practical Questions
6 How does Kelly Wearstler use color to build a narrative
She often uses a monochromatic or tonal color palette to create a specific mood Color is the emotional foundation of the story
7 What role do textures and materials play
They add depth and sensory detail to the story Combining silk velvet metallics or roughhewn stones can suggest luxury history or tactility making the narrative more rich and believable
8 Can you give an example of a narrative outfit for a specific event
For a garden party a narrative might be Botanical Explorer This could involve a linen safaristyle jacket a silk shirt with a leaf print organic wood bead jewelry and structured comfortable heels
9 Whats a common mistake people make when trying to create an outfit narrative
Trying to incorporate too many ideas at once A strong