Thursday, April 18, 2024

Dating duds

Byron Bradshaw examines the do’s and don’ts first date attire


Recently, I received a frantic text message from a friend who was getting dressed for a first date with a woman he met online. “What do I wear?” he lamented.


Choosing the right or wrong first date outfit will either lead to success or failure
Choosing the right or wrong first date outfit will either lead to success or failure

Now, I’ve never been one to be dumbfounded as to what to wear on any occasion. Those who know me intimately can confirm that in whatever free time I can come up with in my day, I try to think of new and interesting ways to make my wardrobe fresh and appropriate for any event. Think of it as my own personal version of the Boy Scout motto, “Be prepared.” Except instead of using flint and kindling to make a fire, I’m using bow ties and pocket squares to create the perfect mix of patterns.


In haste, I described my ideal first date attire (white jeans, chambray shirt, navy blazer, chukka boots) and went on about my day. But it really had me thinking: “How do people dress for dates?”


Last year, the Mail Online reported that in a survey of 2,000 people, 60% of women said that clothes are the top dating deal-breaker. In the same survey, it was found that most women prefer their suitors to wear purple. Yes, that’s right: Purple. The same color as eggplant, gay pride, piety, royalty, and Wimbledon. Apparently, British women like their men to be a vegetarian, tennis-playing, noble who is both queer and religious? I digress.


For most men, I think the absence of square-toed shoes or pleated pants is a “win”. Thousands of New York City barflies might agree. As my grandmother used to say,:“[He’s] the kind of [boy] who can benefit from dim lighting”. But clearly, women are expecting more from their arm candy. So in order to help you guys out, I’ve compiled a quick 5-step rule process to ensure at the end of the evening it’s your headboard banging against the wall, and not just your head.


Rule #1: Be comfortable, but not lazy:

Simply be yourself. Unless you’re a slob. Then be someone else. (Me, maybe?) Leave overdressing for amateurs and underdressing for strippers.


Rule #2: Utilise your tailor:

Man’s new best friend. Or you teach the dog to handle a sewing kit. Either way, your clothes should fit.


Rule #3: No shoes, no shirt, no service:

Flip-flops are not shoes and tank tops are not shirts. Enough said. Save the gun show tickets and foot fetishes for the bedroom.


Rule #4: Accessorise without being messy:

A watch is enough for most guys. Maybe a bracelet or ring if it fits your personal style. Perhaps a singular chain…unless you’re 2 Chainz. Then you do the math.


Rule #5: Wear clean underwear:

You would never imagine this to be a problem, but it is.


Well, there you have it. What do you think, dear readers? Ladies, am I forgetting something? Fellas, what are your personal secrets? I’m looking forward to hearing your comments.


Byron Bradshaw is a New York based fashion entrepreneur who has variously worked for Cameron Silver, Inc. and GQ Magazine. He is a graduate of the University of Texas at Austin.


Follow him on Twitter @ByronBradshaw and on Instagram at byronbradshaw.



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    1. The underwear are dirty because of bad toilet hygiene. They have ample of time to read magazines and newspapers while defecating, but fail to clean their anus and hands effectively. The dirt on the underwear is due to skit marks left, from not using the toilet paper effectively. It is revolting, but true. We live in a permissive society.

    2. Is Byron Bradshaw trying to score a date himself? What does he look like? Many of my female friends are looking for a man currently. I might need to send him off to service them.

        • Strange that he writes a dating outfit article then… But maybe he used these tips and scored. What does he advise my female friends then (other than a bit of Sex at The Post)?

          • Byron is giving us ethical guidelines on how to date a lady not a tart. He is not suggesting a Last Tango in Paris. Sex is a human need but that does not mean that we have to hang on crumpet permanently. Have some decorum, Sex at The Post, remember we are British.

          • Field marshal Idi Amin former ruler of Uganda was also very open about sex. He was interviewed by a Japanese reporter. The reporter asked Amin during the interview what he did in his spare time, He replied “I have sex and more sex. The reporter responded; Mr Amin, you don’t come across as a hostile man. Idi Amin replied”
            Yes, Horse style, doggy style, any style. Sex at the post, be more specific by what you mean by Swedish people being more open about sex?

    3. A man who sews? Byron is in the rag trade, he is expected to have sewing skills, he is a inventor and fashion entrepreneur. We share a common interest in cloth, and have a considerable understanding of its production processes and marketing methods. I was as effective on the rugby field as with a needle and thread in my hand.


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