Party season is upon us—and so too is the influx of outfit conundrums it brings. Allow Dress Code to demystify and debunk what to wear when and where, and how to wear it, as advised by those whose innate style never fails to inspire and influence.
Whether kitted out for morning, noon, or night, Kelly Wearstler’s ensembles are much like her design projects: thought-provoking, dynamic, and endlessly creative. These are not the kind of outfits that come together by accident either. The multi-hyphenate takes a strategic and informed approach to juxtaposing textures and always defers to a high-voltage power silhouette that commands attention and takes up space. With a big night on the agenda recently—hosting a poolside soirée chez Kelly to unveil her experimental gallery and digital platform Side Hustle—it was the perfect time to ask her what runs through her head when she’s standing in front of her closet before a party pondering where to begin.
What s your process for getting dressed? Do you make an effort even when you don t have to go anywhere?
Getting dressed happens the morning of—it’s quick. I’m usually short on time after my workout and mornings with baby Crosby. I dress by mood; it’s all about energy. Some days, the look lands better than others. Once I’m dressed, there’s no time to change. I like to feel inspired, whether I’m in denim or a suit. My style is always evolving; it moves with me.
When you want to feel confident—what boxes does your outfit need to tick?
I reach for pieces that make a statement. In building an outfit, I’m usually drawn to things with structure and texture. I love the contrast between something sharp and something soft. Stepping back, a complete outfit should feel balanced, sculptural, and infused with my own aesthetic sensibility.
A breakfast event pops up for tomorrow. What’s a failsafe outfit for an early morning when you want to feel polished?
Something that has presence—structure, texture, and tension. I always love a wide shoulder; it gives power and proportion. When it all feels sculptural and balanced, that’s the sweet spot.
What type of dress code fills you with dread? And what’s your workaround for that?
None! A dress code is like a creative brief: it’s a chance to experiment and bend the rules.
A luncheon is on the calendar. How might you approach putting together a look?
I’d go for an unexpected material pairing or a statement piece that can subvert daytime dressing expectations. For lunch, I’d choose something that’s playful and off-beat. I love a mini skirt with flat shoes or a vintage t-shirt and platforms.
What are your thoughts on costume parties? All in with the DIY, or politely decline?
All in. Halloween is high-concept dressing. DIY forever: the magic is in the making.
The 5 p.m. slump has hit, but a dinner party is on the cards. What will energize you when shifting from day to night?
Music is my switch: it shifts my mood instantly. My playlists are beautifully chaotic! Tame Impala, Massive Attack, Kendrick, Glass Animals, Jamie xx. I like surprises—the sounds are always evolving, never on repeat.
You’ve no time to think about what to wear for an after-work gathering—what outfit formula always works for you in a bind?
Every day in the studio, I try something new. I m ready for anything and I want to look nice and feel inspired. Every outfit I wear to the studio has the potential to evolve. A change of shoe or a new jacket, and I am good to go.
What’s your read on cocktail attire, in general? What’s an outfit you tend to rinse and repeat?
Cocktail is a great opportunity to try proportions and push the envelope with material and silhouette. I prefer to not play it safe when I go out. I like to make an effort, which generally means trying something new.
What about black tie? Do you like to take risks, or play it pretty safe?
I’d rather take a risk than blend in with convention. I like to push the envelope with proportion and play with curation and form.
What after-dark pieces get the most wear in your wardrobe, year after year?
My bone-colored vintage Chanel bag with small charms that I found in Paris.
Do you have a favorite party-ready piece or accessory that always inspires conversation with strangers?
I love a bow, especially when it’s added with a twist. Something exaggerated or with a print adds a bit of tension, balancing strength and femininity. It’s a classic motif, but when remixed, it becomes sculptural and powerful. Recently, I took a Bode hair bow and wore it as a tie with a full, billowing skirt—it was super cool. I love when pieces get reimagined and start telling a new story.
What’s in your evening bag?
Lipstick, always.
