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Men's Style Blog

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.

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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.

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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.

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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.

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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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... because it's personal

With over 20,000 satisfied clients, Montagio's distinction as the top-rated tailor in Sydney and Brisbane is no coincidence. Our success lies in our commitment to personalisation, ensuring each suit is a true reflection of the individual wearing it. Unlike others, we focus on providing unparalleled service, meticulous attention to detail, and an array of bespoke options, making every Montagio suit a testament to quality and individuality. If it lacks that personal touch, it simply isn't Montagio.

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Meet your tailors

Behind every Montagio suit is a team of expert tailors dedicated to precision, craftsmanship, and personal service. Get to know the masters who bring your vision to life, ensuring every suit is as unique as the person wearing it.

Sydney Tailor James Goodchild

Sydney Showroom

James Goodchild

With over 15 years of experience in suiting and 8 years at Montagio, James Goodchild has custom-fitted over 3,000 suits, achieving $8 million in lifetime sales and earning a reputation as a trusted bespoke tailoring expert. Passionate about bold statement suits and meticulous craftsmanship, he believes true greatness lies in integrity and influence, much like a well-tailored suit that leaves a lasting impression.

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Sydney Tailor Aaron Bry

Sydney Showroom

Aaron Bry

Aaron began his career in 2002 and has deep expertise in tailoring and luxury menswear, achieving multi-million-dollar sales and earning induction into MJ Bale’s Million Dollar Club... twice. Now converted to custom, he is committed to excellence in both style and service and believes in always being impeccably presented. Outside of work, he enjoys bodybuilding and films, often described as a 'gentle giant' for his approachable nature.

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Brisbane Tailor Raul Rodriguez

Brisbane Showroom

Raul Rodriguez

Raul is an experienced tailor with a deep passion for bespoke suiting, combining precision, craftsmanship, and a keen eye for detail to create impeccably fitted garments. Known for his ability to blend classic tailoring with bold, modern touches, he works closely with clients to craft suits that reflect their personality and style. For Raul, a well-made suit is more than clothing - it’s a statement of confidence, sophistication, and individuality.

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Named in GQ Magazine's "Best Tailors" list, and the highest reviewed tailor on Google, Montagio has paved the way for discerning men to get suited up with style. A truly personalised experience, we deliver perfectly fitted bespoke suits, shirts and coats for business, weddings, formal and casual events. Our showrooms are packed with designs that inspire and thousands of fabrics, making it easy for you to get the look you want. Our difference? We won't let you walk out until we've tailored your perfect garment. It's personal. To experience Montagio's red-carpet service, book your personal appointment today.