What if I told you that even I, a fashion editor, sometimes need a little styling assistance? It may come as a surprise, but just like anyone else, I can occasionally feel trapped in a style rut, uncertain about what to wear for a specific event or how to incorporate a new piece into my wardrobe. In the past, when I encountered these moments of fashion frustration, I would turn to Pinterest for inspiration or reach out to a friend for advice. However, this past October, everything changed for me when Who What Wear launched its innovative Intelligent Shopping Assistant, AKA ISA (pronounced ee-suh).
ISA is more than just an interactive chatbot; it has become my personal stylist, product sourcer, and virtual best friend. It offers me endless refined fashion and beauty product recommendations and creative outfit ideas. How does ISA achieve this impressive feat? It harnesses the power of generative artificial intelligence, meticulously trained on Who What Wear’s unrivaled editorial expertise, ensuring that the shopping suggestions it generates are relevant and thoughtfully curated.
With December in full swing and my calendar brimming with end-of-the-year festivities—date nights, brunch catch-ups with friends, and the whirlwind of packing for an upcoming vacation—I realized this was the perfect opportunity to give my brain a much-needed break. I decided to take advantage of ISA’s talents to style me in four outfits tailored for the different occasions ahead. Curious to discover what magical combinations it generated for me? Keep scrolling to explore, and don’t forget to head over to ISA’s chat box for all your styling and shopping needs.
ISA’s Office Outfit Idea
(Image credit: Who What Wear)
When I head into the office in the winter, I always want to dress warmly because my commute is mostly on foot. I also want to feel put-together, which motivates me to do my best work. So, one morning, when I woke up feeling uninspired, I turned to ISA for help with my outfit.
First, she recommended I start with tailored pants that “effortlessly transition from casual to formal” and “ensure I look polished and professional.” I decided to pull out my black tailored pants. Then, she suggested a tan cashmere sweater from Cos, which I don’t own, but I have a similar one from Abercrombie. I styled it with a white T-shirt underneath, mimicking how Cos styled its knit. I added my reliable Sam Edelman ballet flats and work tote from Manu Atelier. And just like that, I had an easy yet elegant work outfit.
The inspired outfit:
(Image credit: @nikki.chwatt)
Shop the look:
abercrombie & fitch
Textural V-Neck Sweater
Manu Atelier
Mini Tote Du Jour Vanilla
ISA’s Date-Night Outfit Idea
(Image credit: Who What Wear)
I often struggle to assemble outfits for first dates, so I’m grateful for ISA’s help. Last week, ISA suggested I wear a collarless jacket, which I had just purchased from our assistant shopping editor Ana Escalante’s story, paired with high-waisted relaxed jeans. I loved how effortlessly chic this look turned out to be—ISA helped me put it together in under five minutes. I can’t wait to see what other date night outfits it styles me in next.
The inspired outfit:
(Image credit: @nikki.chwatt)
Shop the look:
GRLFRND
Sara Super High Rise Slim Straight
Tony Bianco
Bomba Asti Heels
J.Crew
Bordeaux Bag in Leather
ISA’s Travel Outfit Idea
With a long flight approaching in a couple of weeks, I reached out to ISA for some fashion inspiration on what to wear aboard the plane. To my delight, it recommended ALO’s Kick-Back leggings, which made me genuinely happy since it steered me away from the discomfort of jeans. The suggestion was rounded out with ivory ballet flats and a tan wool coat.
I didn’t own the suggested items, and with a budget to stick to, I decided to use this advice as a starting point and rummage through my closet for similar pieces. Surprisingly, I discovered a pair of ivory loafers and a long brown wool coat. When I paired these with my flared leggings, the ensemble exuded a stylish yet relaxed vibe, perfectly suited for my upcoming travel adventure.
(Image credit: Who What Wear)
The inspired outfit:
(Image credit: @nikki.chwatt)
Shop the look:
ALO
Airbrush High-Waist Kick-Back Leggings
ZARA
Ruched Leather Loafers
ISA’s Brunch Outfit Idea
I have to say that I wasn’t surprised by ISA’s performance, especially since it’s trained on the unmatched editorial expertise of Who What Wear. But when I asked for brunch outfit ideas, it confidently suggested a Canadian tuxedo—a chic choice. The clever part is that it didn’t know the brunch vibe or restaurant dress code, so it opted for a classic combination: a denim button-down shirt and wide-leg jeans. But that’s not all—it also recommended a sweater jacket and a silk camisole, which will likely be included in my next brunch outfit. Thanks, ISA!
(Image credit: Who What Wear)
The inspired outfit:
(Image credit: @nikki.chwatt)
Shop the look:
Levi
Iconic Western Denim Shirt
Nordstrom
High Waist Wide Leg Jeans
Freja New York
Mercer Bag Oat
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