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What's The Worst Thing A Man Can Wear On A First Date?

What's The Worst Thing A Man Can Wear On A First Date?

If you're a (straight) guy reading this, you might want to sit down...

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Sarah Clark
Jan 10, 2025
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What's The Worst Thing A Man Can Wear On A First Date?
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Keith Richards

Before we get started (it’s another long one, so get comfortable), I just want to stress that Keith Richards (pictured above) is one of (in my opinion) the most stylish men on the planet (then and now). He’s also one of the coolest (perhaps a post for the future?). But I needed a holding image for this post, and Keith is ticking a few of the first date faux pas here (and pulling them off as far as I’m concerned), and to be frank (call me superficial), I didn’t particularly want an image of a banana shoe (don’t worry, we’ll be getting to those shortly) on my page. So here we are. I also need to caveat this entire post by stressing that, of course Dave Coaches and Timothée Chalemet could indeed wear the exact same outfit and the results would be very different. Ditto Lenny Kravitz and David David Brent. Factors such as age, personality and context are all key here. And as a ‘woman of a certain age’ writing this, of course, the lens is going to be trained through my eyes (with some help from my friends and Instagram followers - thank you all - you literally had me in tears laughing with your responses!!). It’s also been ‘a while’ since I’ve been on a date!! 18 years to be exact. So times, perceptions, and not to mention men’s style and fashion have all changed. But this does not mean we can’t have a bit of a laugh about a subject which, clearly is not exclusively amusing to me.

So let’s start at the very beginning. When I worked at Glamour (between 2004-2011) we used to have so much fun, and there was a lot of banter in the office. The fashion department was open plan, so there was always a lot of chat and funny conversations. This will always be the one thing I miss the most about working in an office with a team of people. Like most offices, there were busier and quieter periods, and during the quieter periods (mostly directly after the bi-annual fashion weeks), the chat would ramp up a bit. Also, during the time, I was a combination of single, dating, and in a relationship. And dating and dates was a regular topic of office conversation. So we would sometimes play a game where we would have to decide what would be the worst thing a guy could wear on a first (usually blind) date? We would literally be in stitches (looking at you Des Lewis!!) - maybe you had to be there? And we would sometimes decide on the worst outfit he could turn up wearing. I think, as I recall, I would also offer up some first-hand examples from guys I had been on blind dates with. I mean, obviously this is all 100% superficial, but at the end of the day, we worked in fashion - clothes were pretty important. And yes, it did matter what a guy showed up wearing on a first date.

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