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How to Dress for a First Date

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Section: Dressing for the Occasion - Blog

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So, do you know how to dress for that all important first date? Do you go extreme casual or should you opt for something with a bit more street cred? Following up on our post of last week on Amazing Date Ideas for a Sydney Valentine's Day, we decided to give you the benefit of our sartorial know-how and help you wow your date on the most romantic day of the year.

Location, location, location

This is your first and biggest tip; consider the location and dress accordingly. If you’re heading to the opera or a Michelin starred restaurant, a custom made suitcannot fail.


But if you’re on the way to a spot of wine tasting in the countryside, cool casual is, of course, the best bet.

Put some effort into your look

Dear old mum knew what she was talking about when she said first impressions count. You want your potential new partner to immediately feel like you made a real effort for the date and, of course, that you have a sense of style. Clean and well-pressed clothes make an impression on the subconscious that can only help in the long run.

Stay in the comfort zone

We’re not suggesting you don the old sweats you wear around the house, but your first date outfit needs to be something you feel comfortable in. The chances are you’ll be feeling fidgety and nervous enough without having to worry about the itchy shirt you’re wearing.


While wearing something new will look great, pants and a shirt that have been worn a few times already will help you feel more comfortable which in turn boosts your confidence; essential for a first date.

Show a bit of character

Whether it’s a colourful pocket square to go with that custom tailored suit or it’s a check shirt in your favourite shade, what you wear says a lot about your personality.

So don’t miss the opportunity to do so by opting for safe colours and styles. Be adventurous but most importantly be yourself; if you find you always wear a shirt and tie then stick to that look, it’s yours after all.

Don’t forget your feet

Shoes! Why doesn’t anyone think of the shoes? Your date arrives and slowly scans you from your impeccable suit all the way down to your battered old brogues. Do yourself a favour and either get the polish out or change your shoes.

Be yourself

Would you drink vodka instead of your regular scotch just to impress your date? It’s thin ice you’re skating on when you pretend to be someone you’re not. Always be yourself in terms of style and personality; you never know, your date just might like it.


If you’re stuck for style ideas for that all important date, then pop into our showroom for a chat, BOOK YOUR FITTING or just leave a comment below. The Montagio men are here to help.


We tailor make mens suits, jackets and shirts for all occasions. Each garment is custom designed, precisely made-to-measure and is guaranteed to fit you perfectly. Unlike others, we offer you end-to-end service and a personalised styling session where we take the time to understand your needs to ensure you get the colour, style and fit you want.

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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.

Simon Frazer

Montagio did a great job on wedding suits for me and my two groomsmen. Bally provided us with fantastic service and the result was definitely superior to an off-the-rack option... more »

Kiran Dosanjh

I have bought a total of 11 pieces custom made so far - quality and attention to detail is spectacular, material choice is broad and the input customers have in creating the exact look they want is a great experience... more »

Roy Soliman

I went back for another suit, a few shirts and some ties. Outstanding! I had so many complements on my new suit yesterday! more »

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