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What Should I Wear on a First Date?

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Section: Dressing for the Occasion - Blog

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Ah, the sweet dilemma of what to wear on the first date! Should you opt for the security of a tailor made suit, or venture into uncharted waters with a more casual look?

You can’t control all the factors of a first date, since everyone is unique in tastes, opinions or hobbies, but you can control your image. Here’s how to nail it and stack the cards in your favour when you step out for that first date. Just follow these simple do’s and don’ts, and you’ll always feel comfortable on any first date.


Wear tailored suits unless you are attending a dress code specific event that specifies formal or casual attire.


A well-made custom suitgives you these advantages:

  • It accentuates your shoulders, trims your waist, and makes you look taller and slimmer.
  • Shows your respect for your date – after all, she’s sure to be dressed to the nines herself!
  • Being well-dressed gives you an air of confidence and increases your feelings of self-worth.

Matchy Matchy

Also, always match socks and shoes to trousers colors. You’ll earn “extra points” with your date if your shoes are polished to a high shine.


If you must dress casual, but don’t have time to change, soften the look of your suit by taking off your tie, unbuttoning the top button of your suit, and ditching your suit jacket.



  • Avoid baggy trousers or ripped, holey or distressed jeans – they send the wrong message.
  • Stay away from boring neutral tones.
  • Don’t wear socks with sandals unless you want a first date to be a last date.

Lastly, make sure you and your date are on the same page regarding dress code. This ensures she has the right impression of what the date is going to be like. For example, if you're heading to a formal location, she would feel uncomfortable attending it in a more casual outfit.

Would you appreciate some personal advice about choosing the right clothing to impress your date? Call our Sydney showroom toschedule a no obligation styling session today.

Original idea for article from Antonio Centeno, author of the internet's most actionable men's style guide. We recommend a read!

Image Credits © Redbaron | Dreamstime.com © Igor Mojzes | Dreamstime.com © Lisa F. Young | Dreamstime.com © Volodymyr Ivash | Dreamstime.com


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Since 2010, we've paved the way for uncompromising men to get suited up in style with our full service tailored mens suits, shirts and coats. Our showrooms are packed full of suit samples and thousands of fabrics making it easy for you to get the look and fit you want. We offer a remarkably personal shopping experience and specialise in individually hand crafted garments for business, weddings, formal and casual events. We have personally tailored mens suits for thousands of happy customers, and you too can experience the same red carpet treatment. Book your personal appointment today to have your uniquely styled and perfectly tailored garment ready within a few short weeks.

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