A Girl’s Group Chat Tells Us What Not To Wear On A First Date
— Updated on 20 June 2023

A Girl’s Group Chat Tells Us What Not To Wear On A First Date

— Updated on 20 June 2023
Sera Bozza
Sera Bozza

DISCLAIMER: The tragic experiences and all views expressed in this text have been sourced from one girl’s group chat. ONE. It took some coaxing for the individuals to be able to share and reflect on their trauma. Therefore, I have renamed each contributor to protect their privacy. Each encounter was cloaked in layers of shame. 

But gents, the shame is not on us. It is on you. You had one job. 

We want you to do well on a first date. We really do! If we’ve met on an app, we’ve likely committed to a week of timely banter with you, excessively checking our phones, and stalking your ex on social media. 

If we have met out on the town, there’s been even more physical energy exerted. We spotted you from a mile away, and edged closer, in heels, until we finally got your attention. Do you think you spotted us first? Cute. 

In the lead-up to the date itself, we have (at the bare minimum) paid our dues by washing our hair, applying (and then immediately strategically removing) fake tan, for that perfectly balanced “natural” glow, and lastly, having our outfit reviewed by a close friend.

Imagine, our shock and horror when, after all that time, commitment, and overthinking – sure your ex was blonde and I’m brunette, but stranger things have happened – no longer makes the slightest difference. 

Because after we see you, and what you are wearing, our whole promising future together goes entirely to shit.  

And then we have to endure at least 45-60 minutes of soul-destroying polite chat, long enough for you to go to the bathroom, so we can message our friends to tell them how you decided to rock up to our first date at a speakeasy cocktail bar. 

“He’s wearing an Akubra.”


“An Akubra with a slogan tee.”

I have grouped the offending items below, broken down by category. 


Steph: “Chocolate brown leather moto jacket.”

Ella: “Omg. I had one of them too! Did it have the weird no-collar thing?”

Steph: “Yes! With a press stud.”

Chloe: “And elastic on the wrists :'(“

Steph: “Shit, you too?” 

Chloe: “My guy kept pulling things out of his front pockets. The brown was like faded with overuse.”

Ella: “I remember him! The magician!”

Chloe: “Yeah! He pulled out lip balm, an eye mask, boarding pass, and just lay them on the table. I asked if he had recently been on a plane. He said no?”

Em: “He wore a Fred Perry. Vest.” 

(String of OMGs and head-exploding emojis)

Em: “… that he got, on sale.”

Steph: “How do you know it was on sale?”

Em: “He wouldn’t shut up about it.”

Bella: “What’s wrong with Fred Perry?”

Ruby: “Wow.”


Maddy: “He stood up from the table wearing black harem pants.”

Steph: “That’s horrific.”

Maddy: “Look! I snapped a photo when he was at the bar.”

Sends attachment.

Chloe: “He looks like 2Pac.”

Ruby: “Worse. More like, a Japanese Samurai?”

Bella: “Why is there so much material? It’s just excessive.”

Maddy: “And! He was drinking a beer out of a horn!” 

Steph: ‘Lol! Did he take you to that Viking-themed bar?”

Maddy: “Yes! I had no idea what it was. It was all just too much.”

Chloe: “Once a guy came in a Deus Muscle tank, so loose and so worn, that I could see his nipple the whole time.”

Em: “Ew. Just the one nipple?”

Chloe: “Yeah! It was just staring at me, deep into my soul. I felt so exposed.”

Amy: “He wore a Superman shirt on underneath his business shirt to give him confidence.”

Ella: “It doesn’t sound like it worked…”

Amy: “No. No, it did not…”


Bella: “Fingerless gloves.” 

Chloe: “Why is that still a thing?”

Maddy: “It’s not a thing.”

Bella: “I know! I felt obligated to comment on them. To like, acknowledge we were both in their presence… So I said “cute gloves.” He said, “Thanks! my mum knitted them from our pet alpaca.”

Chloe: “I can’t. Was this in Melbourne?” 

Bella: “We were on Chapel Street in Windsor. I wanted to die.” 

Amy: “He messaged me that he had arrived…’I’m at the back in a Jazzy scarf.'”

Em: “And did you immediately turn back around?”

Amy: “It was too late. He propped it up on the table too! Like a trophy. I took a photo when he was in the bathroom and sent it to my friends.” 

Sends attachment. 

Ruby: “Omgg, I’ve seen it on Hinge!”

Amy: “My friends spotted IT out later that night!”

Maddy: “IT IS SO OFFENSIVE. Get it away!”

Amy has deleted the attachment.

Chloe: “He stopped and put on a pair of slimline black leather gloves.”

Ella: “Chloe. You didn’t need to go through that alone. We’re here.”

Chloe: “Thanks, guys. It was summer? It was warm? My eyes kept darting to the nearest bins. I thought he was going to slice me up.”

Steph: “A leather satchel.”


Ella: “He rocked up, barefoot.”

Steph: “Was he…”

Ella: “No. He was not hot enough to pull it off.”

Maddy: “Wow. What did you do?”

Ella: “We couldn’t get into a bar with him dressed like that, so he took me to Boost Juice.”

Em: “White loafers.”

Maddy: “Faded brown crinkly business shoes.”

Chloe: “Make it stop!”


Ruby: “Surprise cornrows, dressed in bootleg jeans with polished black dress shoes.”

Multiple responses of clapping hands emoji. 

Ruby: “Haha yeah like maybe I could have dealt with one of those items in isolation? But I got the trifecta.”

Bella: “He wore a wetsuit because he came from the beach.”

Chloe: “That’s fair?”

Bella: “Except we met hours after. In the suburbs.”

Steph: “Yep, that’s the hook!”


Sometimes, less is just the best. Strip down your choice of options to some of what’s listed below, and then feel free to combine them as you see fit. Always dress appropriately for the climate, and the occasion.

And I hate that I actually have to emphasize this, but everything should be clean

Consider the following:

  • A quality plain tee, ironed so the neckline and pockets look like new. 
  • You absolutely can’t go wrong with a button-up shirt in muted colour palettes. Opt for experimenting with different textures of shirts, over introducing bolder colours or patterns. 
  • A nice cut of jeans, that aren’t ripped or excessively faded.
  • Well-fitted chinos. We don’t want to look down and see the material hanging on for dear life around your quads. 
  • A fitted blazer will basically dress up anything, but only suits the right location. 
  • Always have a pair of crisp leather sneakers and a good pair of dress shoes on hand. 
  • If you’re coming from the office in a suit, you’re probably good to go.  

When you think you want to add an accessory, just don’t. But if you are sticking with your guns, at least ensure the item is in a muted colour palette. And never anything knitted from your mum.

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Sera Bozza


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