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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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You know dressing appropriately for that first date is vital, but you may be unsure of exactly how to go about it. Here's the lowdown on what to wear to make sure the first impression is not the last impression.

Men need to dress well for a first date. After all, since you don't know if this date will lead to you making the biggest commitment of your life, it's best to dress in a manner that shows you take your dating partner seriously.

Why Dress Sharply for a First Date?

Clothes cover about 90% of your body. Worn correctly, they enhance your positive features and diminish the effect of those that are less attractive. When you dress sharply for a woman, it shows that you take her seriously and respect her. Women, in general, invest a lot of time preparing for a date; by looking your best, you reciprocate.

A well-dressed man demonstrates he is adept at socialising. Women's opinions are not formed solely by the man's interactions with them; they also evaluate the way he interact with others. Typically, people form opinions about an individual based on clothing. Hence, by looking sharp, nodding politely and smiling, you leave people with a positive impression.


The right clothes influence your frame of mind. For example, uniformed soldiers can focus on tasks better. This same theory works when you dress for a date, so take time to prepare and wear clothing that makes you look and feel confident.

The right clothing can emphasise healthy masculine traits. For example, a sports jacket draws attention to the square lines in the wearer's face, his broad shoulders, muscular chest, smaller stomach and broader upper torso.

Both parties check each other out on a first date, seeking clues about the personality and long- term potential of the other person. Since you'll only spend a few short hours together, your clothes, your conversation, and your body language (collectively) help your date decide whether or not to meet again.

Tips for Dressing Guidelines

There is a difference between casual dress and dressing sloppily. If you are interested in future dates with someone, avoid wearing clothes that might give the other person the impression you didn't make an effort to dress up.

For example, don't wear ragged or torn blue jeans, sweatpants, athletic pants or work clothes on a first date. Instead, consider wearing dark-wash jeans in black or deep indigo. These are versatile, sharp looking garments and can be paired with anything from a short-sleeved shirt to a business shirt and sports jacket.

Tuck in your shirt and wear a leather belt and shoes in the same colour family. No running shoes on a first date, please! An oufit like this is comfortable and fashionable for a casual date.

Jackets are a must for dinner dates or evening events. Wear a blazer jacket if the occasion does not require tailor made men's suits. For daytime dates, a sports jacket can be a more casual option.

If the date consists of a visit to the city theatre or the opera, it's important to dress up for the occasion. A good looking men's suit partnered with a clean, well-pressed business shirt and tie is the ideal outfit. Always pay attention to your shoes – your date will be certain to check them out. Your footwear should be clean, functional and stylish.

Grooming Tips for a First Date

  • Hair: Follow your usual grooming routine and avoid trying anything new just before your date. If needed, get your hair trimmed a week prior to your date.
  • Cologne: Wear a conservative cologne with a suble fragrance that won't overpower your date.
  • Miscellaneous: Clean and trim fingernails; trim nose hair and any stray hairs at the back of the neck or on sideburns.
  • Final Tips

If you need to update your wardrobe so you'll look amazing on a first date, invest in classic clothing instead of fashion pieces that will be hard to match with other items in your wardrobe. For example, a light blue business shirt with a slight pattern is easier to match than a bright blue shirt with a printed graphic design.

Maintain a wardrobe of two sports jackets, a few pairs of interchangeable trousers and jeans, and six to seven classic business shirts, and you can be dressed for almost any type of date in a matter of minutes in a variety of combinations.


Limit accessories to a boutonniere on your lapel, a quality timepiece, and a pocket square in your jacket's breast pocket. Remember: Less is more! Make sure both of you are aware of the itinerary so you can dress accordingly.

A last word of advice: clothes are crucial but can only win you the lady's attention up to a certain extent. Beyond that, the onus of creating a favourable impression rests entirely on you via your manners, your sense of humour, and your ability to hold a stimulating conversation.

Are you feeling a little panicky because you have an important first date coming up but you're not sure what to wear? Take the pressure off yourself andpop into our Sydney showroom for some expert advice from the men of Montagio. We're ready and waiting to dress you in the finest sartorial style that will cause heads to turn when you enter the room.

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

Image Credits: © Poznyakov | Dreamstime.com © Volodymyr Ivash | Dreamstime.com © Gstockstudio1 | Dreamstime.com


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