Editors on What They Wore on Their First Dates

Editors on What They Wore on Their First Dates (And What They’d Wear If They Got a Do-Over)


February 12, 2019
Read Time: 3 minutes

There's nothing quite like the first



Most of us are taught to believe that first impressions are everything––and it’s for this reason that we pour our hearts and souls into the first ensembles we wear to everything. First day of college, first day of work, first day post-dye job (I committed to a week-long streak of white t-shirt dressing because they made the pink hair I eventually achieved look best). Firsts are milestones in themselves, aren’t they?


In the spirit of love month, Wonder zeroes in on another unforgettable first on the timeline: the first date. Relishing in the nostalgia and perhaps even a little retrospective cringing, we took to our social circles to ask about the first date looks of some of the best-dressed gals out there: editors. What did these women, armed with the gift of sartorialism and style, wear on their memorable first dates? And more importantly, would they choose to wear the same thing if they got a do-over?


RELATED: 2019 Trends to Wear and Ignore (Plus Where to Get the Look!)


Editors on What They Wore on Their First Dates (And What They’d Wear If They Got a Do-Over)

Angela De Dios
Features Editor, Star Style


What I wore: I can't exactly remember how I looked on my first date. But I do remember one of the outfits I wore early on in my first high school relationship back in 2007. It was nothing formal, we just went to the mall to have dinner and watch a movie. So I thought a white T-shirt would look casually cool with a denim mini skirt.


What I would wear today: Looking back, I'd probably wear it again. I've always been the kind of girl who'd choose classic over trendy anyway. And how can you ever go wrong with a white tee and denim combo? Although if I could change one thing, I would have matched my outfit with a fancier pair of flats, rather than just thong sandals. But then again, it was just the movies, so even a pair of white sneakers would do!


Keep up with Angela's outfits and globe-trotting adventures on Instagram!


Editors on What They Wore on Their First Dates (And What They’d Wear If They Got a Do-Over)

Yanna Lopez
Editorial Assistant, Preview.ph


What I wore: Man, it wasn't a first date, but on one of my most memorable dates with an ex I wore a beige shift dress and nude pumps. Boring, I know, but at the time I was a uni student and barely had a wardrobe outside of tiny denim shorts and floral tank tops! It was very, like, excessively safe.


What I would wear today: Either one of my token wacko print-on-print-on-print outfits or the black calf-length bodycon turtleneck dress I wear 50 times a week. And sparkly shoes. And red lipstick, just to be even more intimidating. Mindset: if my lewk doesn't scare him off, then he's potentially a keeper!


Learn a thing about layering prints (SO many of them) from Yanna's online style diary on Instagram!


Editors on What They Wore on Their First Dates (And What They’d Wear If They Got a Do-Over)

Nicole Blanco Ramos
Writer, Wonder


What I wore: Oh yes. I wore an LBD with a loose-fit blazer and a strappy cage heel. A classic! And pretty generic. But I was strategic about this choice; I had to make sure the dress granted me enough tummy allowance to eat, hahaha. Nothing worse than feeling uncomfortable during a date.


What I would wear today: I pretty much dress the same way now: I still wear a lot of black and still love me a good blazer. I would probably nix the heel though and trade it for a pair of sleek ankle boots.


RELATED: Our Favorite “How We Met” Stories from Real People



Do you remember your first date fit? Would you rather repeat that look or pretend it never happened?



Art Alexandra Lara


Most Popular

Notify of
Inline Feedbacks
View all comments


Subscribe to our Newsletter

Don't miss a thing

Stay up to date to the latest news and articles.