I Asked a Bunch of Strangers What They Thought of My Outfit

Emma let people ask her anything AMA

As an outgoing introvert, it’s easy for me to talk to lots of people despite how tired I’ll ultimately be when all is said and… said. Forever straddling the line in true Gemini fashion, I often find that my personality is in constant struggle with itself. This struggle was something I had to work through the other day for the sake of very important journalism: I wanted to know where people — strangers on the street — would think I was going in a wild outfit styled by Leandra herself.

For this endeavor, I wore an Entireworld gray-and-navy striped sweater styled over a purple Tibi half-zip, a silver mini skirt from Topshop, and a classic (bold?) sock and sandal combo: navy blue Hue knee socks slipped into navy blue Birkenstocks. The outfit was made up of elements I would be more inclined to wear separately than together.

The tops both had really good body-feel (very soft! lots of give! the layers did not impede my mobility in the slightest!) and I felt mostly good in the look, although it was my first time wearing Birkenstocks and I didn’t love that part. This particular model featured straps that cradled the backs of my ankles and felt like seatbelts for my heels. My feet were secure but also forcibly confined to the cork-bottomed contraptions, which also happened to be a smidge too small. I’m not sure if they run tiny or if my feet have grown, but that’s beside the point, which is: I asked strangers to judge me because I wanted to know some things. How would letting someone else take the wheel of my personal style-mobile affect my ability to talk to people? What does Soho think of metallic skirts? Are socks/sandals as polarizing as one may think? CAN CLOTHES INSPIRE REAL HUMAN CONNECTION AMONGST STRANGERS ON THE STREET? Answers to these questions and more below.


The first person I asked told me he thought I was going to heaven. “YOUR version of heaven… because your version of heaven is different than my version of heaven or anyone else’s!”

Well, thank you kindly sir. Glad I don’t need to repent first — for wearing sandals with socks or any of my other many sins.


“I have no idea where you’re going,” said a man who was also nice enough to put the phone call he was having on hold while he entertained my questions. “A space party or something?” This he calculated after sizing me up, but not in a way that made me feel disrespected. “Where am I going in MY outfit?” he wanted to know. Fair question.

“To work?!” I quipped back, taking in that he was standing too casually in the doorway of the light shop to simply be a customer and also that there are quite a few lighting-related stores on Bowery.


“Hi, can I ask you all something?” I had stumbled upon what I thought to be a gaggle of movie extras milling about on the corner of Kenmare and Bowery.

“Sure,” said the most formal-looking guy. He was wearing a polyester suit and hard-bottom shoes.

“Where do you think I’m going in this outfit?”

“I haven’t the slightest clue.”

“What about a guess?”

“Um… a party?”

“A specific kind?”

“A specific kind of party? No.”

“That’s fair.”

“Where ARE you going?” he wanted to know.

“I’m not going anywhere… I just wanna know where people think I’m going.”

At that, both his mood and tone brightened, and I realized that maybe people don’t like being asked questions to which they are led to believe there are specifically desired answers.

“Honestly, I would have thought it was just an ordinary, everyday outfit. But because of the fact that you asked me ‘where do you think I’m going?’ I figured you might be going somewhere.”

“I could be,” I told him. “Maybe the better question is ‘where should I go in this outfit?’”

“Where would you like to go?” He offered. I told him that was a great question.

“Once you ask all the questions, you can finally come to an answer,” the sidewalk sage professed before I thanked him and continued on in my quest.

4. & 5.

“Excuse me, can I interrupt you two for a second?”

Leandra had suggested I go to a coffee shop or park to do this reporting — a bunch of people in the same space would make the work easier for me and interviewees more likely to participate, but I like the challenge of stopping strangers on the street. It makes reporting like a box of chocolates in that you never know what you’re gonna get.

“Where do I think you’re going? NOT the Upper East Side!” said the husband half of the older couple I was chatting with. I had stopped them because they looked like tourists and I thought my skirt would spark an interesting conversation.

“Why not?” I asked, as the wife chimed in, “Fashion Week?” with an earnest chuckle. The only thing breaking up her monochromatic black look (button-down, jeans, ballet flats) was a brown quilted Burberry jacket and her opinionated partner.

Turns out he was more focused on my purple top than my silver skirt. “Well, I don’t see much purple in the Upper East Side,” he said. I told him the half-zip was Tibi, so it could in fact be an Upper East Side look, to which he agreed.

The wife deliberated a bit more. “Jeez, I mean… Soho?”

“Just out, shopping?”

“Out… shopping…” said the wife, with the husband adding, “Doing your thing. The socks and your sandals…” I don’t know what he said after that because his wife was telling me I looked “very cute” over and over again and I chose to listen to her.

“Thank you very much!” I said before darting off to gather more opinions.


A man who looked like a fisherman said to me, unprompted:

“You like silver.”

“I like silver?”

“Yes. You like silver.”

“And where do you think I’m going in this silver?”

“That way,” he said pointing north, which was in fact the direction in which I intended to go.


“I don’t know… this is just like the stuff I wear to class!” I had stopped the coolest college kid in all of New York state.

Man Repeller earring and barrette (coming soon!)Man Repeller earring and barrette (coming soon!)


“You’re in New York, you could be going anywhere! You could be going to work, you could be going to your job at your startup, it’s not really THAT weird. The skirt is a little metallic-y… and I don’t know — socks and sandals? Is that a thing?” I was talking to a man with dark hair and a loquacious lilt.

“You’re not drab,” he continued his analysis. “You’ve got color, you’ve got statement stuff going on, but you’re in New York… there’s so much of that, it doesn’t really stand out that much. It would in other cities. But here… I noticed your hair before I noticed your outfit.”

The hair comment caught me off guard and I auto-piloted a “thank you.”

“I like that hair. Don’t change… Who is this story for?”

“Man Repeller.”

“Hmm… we notice other things before we notice what somebody’s wearing. Unless it’s like… insane.”

“What’s insane?” I wanted to know.

“I don’t know, some kind of Alexander McQueen feathered concoction, sure we’d notice that, but just some… you know, you’re a fucking hip New Yorker on your way to your cool job and you know, you’d have to go a lot further out than that. Like, stuff that you see in runway shows — but no one wears that. Maybe they do to some crazy rich person’s party on a yacht. But most people can’t afford it first of all, and it’s over the top. And as far as men… I don’t think men care. The premise is true, high fashion and stuff doesn’t attract men, but it doesn’t repel them.”



“A party probably? A pre-Halloween party.”

This man was a cook, standing outside of his restaurant. Pre-shift. I wanted to tell him all about my childhood obsession with the Food Network and my famous waffle recipe and somehow convey that I can throw down in the kitchen, but instead I just said, “I wish!” I wish I were a chef. I wish I had been going to a pre-Halloween party.


“You could just be coming back from an after-hours,” said a man smoking on his stoop.

“I like where your head is,” I told him. “It’s possible!” This guy had the look of a Berlin house DJ so of course he knew about the afters scene, but how did he know that I used to throw parties!? His comment brought me back to the days of dragging myself home from a night of work at 10 a.m.

“Either that, or going to a disco party,” he said. “You look great, so wherever you’re going, I hope you get there.”

Heaven, here I come.


“Hey sis, how you doing?” This next woman probably thought we would just exchange pleasantries, but she had initiated conversation with me and I was not about to let the opportunity for more reporting go to waste.

“I’m doing well, thanks! Where do you think I’m going in this outfit?”

“I don’t know… I hope not to the go-go club!” she laughed. “To the moon? To a photo shoot?”

“No, but I did just have one,” I told her.

“I see you got rose-tinted glasses on, that’s cool. You need ’em nowadays!” She’s not wrong, but our interaction would have looked good filtered through anything.


“Where are you going? I think you’re just living your best life, and you simply wanted to look fly as fuck. I think you were just dressing for you — I don’t think you’re really going somewhere. I don’t think someone needs to dress for an occasion to look good… you’re just trying to get out your house and look like a bad bitch.”

Takes one to know one, I think.


“You’re going to the Roxy Hotel to meet a friend who’s in town to have an afternoon drink before she leaves for the airport. You clearly have a look going on — but: You guys were trying to get together for the past couple nights — you’re both really busy but you wanted to see each other, and you were like, ‘Well I can’t go in bupkis, but it’s also a little bit too early to run in full shoes.’” It was 3:45 p.m., the perfect time to begin wondering if “full shoes” is a phrase one should immediately incorporate into one’s vocabulary.

“And you also have New York Pilates after so you threw on Birkenstocks with a sweater that matched to make it a little more fun. You’re wearing your gym outfit underneath. It actually all matches; this makes sense to me. I guess I’m your demographic, so to speak.” Also my star interviewee, so to speak. I’ve heard that you’re more likely to get pulled over while driving within a mile of your home, but they fail to tell you is that the best reporting can happen steps away from your place of work.

14. & 15.

“Class. Normal class. You’re going to your economics class. You just look… normal. I would wear this on like, a day off. A regular Monday. This is not shocking at all. It’s just silver. You could be going to the supermarket.”

Her friend chimed in: “This is the kind of response you get from a fashion designer.”

“And what about you, where do YOU think I’m going?” I asked the man who was probably not a fashion designer.

“I mean, I love the purple — I literally just came back from our reunion, and our colors are purple and white — I love anything with purple in it.”

“High school reunion?” I don’t know anything about reunions; I’ve never been to one. I also can’t tell how old people of the melanated variety are. I myself can present as 12 or 45 on any given day.


A man in a maroon heathered hoodie catcalled me in a sickeningly low voice as I walked by him on Bowery. “Sexy.” I turned around to meet his stare; it was stuck to my body like a fly trapped in molasses. We shared a strip of sidewalk that was cloaked in the shadow of renovation — the building behind us was undergoing some work putting the walkway under semi-permanent cover which made this whole interaction even scarier. I refused to ask him where he thought I was going because I didn’t want to be street-harassed any further, but the next person I asked told me that I could be going anywhere. To a land free from the effects of heteropatriarchy? I wondered.


“I’m in the arts, I see clothes like this all the time!” a very friendly woman told me outside of the New Museum. “I like the blue [of the Birkenstocks and the socks]… things don’t have to match anymore. I forgot the new museum was closed today… who ya doing your story for?” I liked the way she talked.

“You gotta ask the right people,” she advised. “Ask this guy here! With the blazer… he’s trying to be very straight, very business-oriented.”

18., 19., 20. & 21.

Turns out my museum friend was right. “It’s not MY style, personally,” the guy said in a very French accent. He didn’t have a guess as to where I was headed, but his friend did: “A kitsch party?”

Everything they said made me smile — I think it was the accents. I thanked them after everything they said because it all sounded complimentary.

“I wanna hear more about this not being your style,” I said to the man in a blazer.

“Now… I’m a classic man.” He told me.

“He was born like that!” the kitsch party girl agreed.

“So color is not my friend. I am SO SO SO classic. Too much.”

Now this was intriguing to me. “Classic means no color?” I asked.

“Mmmm… no colors. Plural,” said the man who prefers a very subdued palette. “But a good button? Or a beautiful… le pas?” I must admit that I don’t know if that’s EXACTLY what that last thing he said is because my French is much worse than it should be as someone who studied critical theory for years. Regardless, I got the impression that this man is only willing to be sartorially adventurous in very controlled way, leading me to believe that both his moon and rising signs are Virgo.

The fourth member of their group asked if I was going to a hippie party on the beach. I wondered later if it was my amethyst-tinted lenses which led her to this conclusion and felt a little bad. Did I deceive this woman? The glasses were not part of the styled look, but necessary for my being able to see. I hope I still get to go to heaven.

Photos by Starling Irving. 

Emma Bracy

Emma is the Associate Editor at Man Repeller.

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