How to Talk to a Tech Guy About Fashion

Five tips to help humanity move beyond hoodies and flip-flops.


A couple of years ago, tech programmers and fashionistas would have parted ways after algebra, never to meet again. But, these days, everyone seems to work at a company that is tech or tech-adjacent. And, we’ve noticed a strange, growing phenomena: the fashion-conscious woman and the nerdy tech guy have started to rub elbows more frequently in the workplace. At Tradesy – which is a fashion and tech company, we find this connection both adorable and odd (think Richard and Monica from Silicon Valley). Because we have so many programmers who are knee-deep in fashion-speak, we have thoughts on how a stylish girl can talk to a software engineer, dev or IT guy about clothes. Why? Cross-cultural communication, of course! And the sincere hope that we can one day move beyond hoodies and flip-flops.

Here’s our list:

1. USE ANALOGIES THAT MAKE SENSE. How to explain Fashion Week? High-couture seems impractical, unwearable and ridiculous, let’s be honest. But, it is also really creative – and the ideas trickle down to the things that most of us buy. Explain to your software engineer that Fashion Week is like TechCrunch Disrupt, except with models. Not every idea at Tech Crunch Disrupt is disruptive. But that’s what everyone is trying to do. Tell them the whole purpose of Fashion Week is to be as disruptive as possible. With clothes.

2. BE SUBVERSIVE. Engineers value comfort and practicality, which is sometimes the opposite of fashion. But, sweatpants, basketball shorts and those blue, stripe-y Adidas flip-flops make people think of sweat. Gross! We suggest being subversive: “What if all the women in our office came to work wearing sweatpants?” That should put the whole thing into perspective.

3. GO HEAD ON. When it comes to Ed Hardy, you just need to be direct. Say: “I’m really sorry, but just don’t. Wear. Ed. Hardy. Say that. It’s fine. You can take a feminist stance on this one. Don’t feel bad.

4. APPEAL TO LOGIC. Generally speaking, some engineers dress better usually because they have wives or they are gay. Good for them! They have guidance. If you see a heterosexual, young engineer wearing Adidas flip-flops and a hoodie, we suggest you appeal to their practical side. Make a gentle suggestion: “When guys dress well, women are more likely to date them.” If it falls flat, gift them a nice sweater for their birthday and a premium Tinder subscription.

5. TELL THEM THE TRUE STORY OF STEVE JOBS’ TURTLENECK. Some software engineers may say: What about Steve Jobs? He cared so little about fashion that he wore a black turtleneck every single day. This is a great opportunity to talk to a software engineer about fashion. The story of Jobs’ black turtleneck is actually quite interesting. According to Walter Isaacson’s book, Steve Jobs was always fascinated by the idea of a uniform and even tried to get Apple employees to wear a uniform designed by Issey Miyake (it didn’t work). He then asked Miyake to design a turtleneck just for him. Miyake sent him over 100 black turtlenecks. With enough beautifully-tailored turtlenecks to last him a lifetime, Jobs made a decision: wearing a turtleneck was not only convenient, but also gave him a signature look. What? Steve Jobs actually thought about having a look? 

He did. Maybe the rest of us should too.

Next month stay tuned for part deux: How to Talk to Your Marketing Person About Coding.

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