How Does A Gentleman Dress On A First Date?

First dates can be nerve-wracking: no matter how many someone has had, it is still easy to worry about the smallest details. A lot of thought can go into a first date, between scheduling, thinking of conversation topics, and deciding what you are going to wear. So how does a gentleman dress on a first date?

Tossing on any shirt and jeans and hopping out the door is easy, but a gentleman knows that his attire is his canvas. It's his way of telling the world who he is, what he stands for, and how he carries himself. When you put extra thought and effort into how you dress, you will not only look better but also feel better. 

Consider The Location Of Your First Date When Piecing Your Outfit Together

Dressing for a first date doesn't need to be an extensive ordeal. Some careful planning should be involved. Consider the location. Is it formal, or informal? What activities will be included? 

Are you planning on just a casual dinner, or is there a possibility you may be active (like going for a walk, painting, or getting your feet wet at the beach)? You wouldn't wear a three-piece suit to the beach nor would you wear swimming trunks to a nice restaurant. By asking yourself these questions, you can begin to curate what you should wear on the date.

Looking for date ideas? Here is a list of 15 cheap date ideas that won't break the bank!

Make Sure You Wash Up Before Your Date

First a foremost, take care of your hygiene. That means showering, shaving (if you don't rock a beard), and tending to your body. Consider a haircut from a trusted barber if your hair is becoming unruly. 

If you don't have the time, you will have to work with what you have. Try different styles and products. Deodorant or antiperspirant is a must. Brush and floss, make sure to get in all the spaces between your teeth and scrub your tongue.

Read our checklist article Men's Hygiene Checklist: The Ultimate Guide to be squeaky clean and totally prepared for that big date! 

If you are worried about having bad breath, invest in a tongue scraper. These tools are designed to remove harmful bacteria, the ones that cause bad breath among other things like cavities, off of your tongue. They're relatively inexpensive and a great tool to have for that extra clean feeling. Healthline goes into more detail on the benefits of tongue scraping here.

Be Sure To Wear A Fragrance On Your Date

If you're planning on wearing cologne, only a couple spritzes on your neck or behind your ears will do. Consider something light for the first date. You want your scent to be discovered, not pronounced. If you are going to be applying a fragrance, be sure to use unscented deodorant or antiperspirant so the scents don't mix with each other.

The benefits of wearing a fragrance are plenty. We review several of the most important ones in our article 9 Fantastic Reasons To Wear A Fragrance.

Some people may have adverse reactions to fragrances. Be mindful if you are in a busy environment. Don't douse yourself in fragrance. You want to be discovered, not announced. Wearing too much cologne may make others think that you haven't bathed in a while.

Consider The Formality Of Your Date And Dress Accordingly

If the date is more on the casual side, a simple polo shirt and shorts, colourful chinos, or dark-wash jeans is a fool-proof choice. Not only will the polo shirt be a step up from a t-shirt, but combining it with dark-wash jeans or shorts shows that you're relaxed and have a sense of cool casual style. You can pair the outfit with loafers (with shorts and chinos) or canvas shoes (with jeans) for a laid-back look.

Always make sure to take care of the small details in your outfit.

Wearing a watch can increase your style. It's one of the few pieces of jewelry a man can wear regularly and sends the message that he cares about his time. You don't need to spend a fortune on a nice timepiece. Check out our article on How Many Watches Does A Gentleman Need? for some inspiration.

If the date is more formal, you don't need to go all out with full white- or black-tie unless you're going to a Michelin restaurant with a four-figure bill. A smart casual or semi-formal look, such as a dress shirt or patterned button-up shirt under a blazer, paired with chinos and dress shoes, shows that you have a sense of style and are able to dress up. No need to break out the office suits on a date, unless you're there to sign deals.

You can add a pocket square and/or tie if you want. It does take a bit of skill to properly match a tie/pocket square to your wardrobe. A couple rules of thumb are:

• Never wear a matching tie and pocket square. The colours should compliment each other, not match.

• Your tie/pocket square colours should be accent colours, not the main colours in your outfit. They shouldn't blend in but rather stand out a bit using colours that compliment the rest of your outfit. Read our article on the colour wheel to learn what colours work best together so you can create a harmonious outfit.

Remember that it's better to dress up for a date than to dress down. It's easier to remove layers than to add them. If you enter a restaurant wearing a blazer and no one else is wearing a blazer, you can simply take yours off and either hang it up or put it beside you at your table. If, however, you enter a restaurant and are the only person not wearing one, you may get some looks from the patrons and staff.

If you want more information on how to be a well-dressed gentleman, we go into more detail in our aptly named article How To Be A Well-Dressed Gentleman.

Avoid Wearing The Following On A First Date (Or Any Date): 

• Logos. You're not there promoting a brand or band. Leave the logos at home.

• A "witty" shirt. We've all seen them—"the man, the legend". You might find the saying amusing, but your date could find it childish and offensive.

• Distressed/ripped jeans. Unless you're going to a concert, leave the ripped jeans at home. You don't want to look like you just fell off your skateboard.

• Shorts. Unless you live somewhere where it's incredibly warm or you sweat a lot, avoid shorts on a first date.

• Sweatpants. You're on a date, not cleaning the house or lounging on the couch.

• Tons of jewelry. Keep it simple, with a watch and maybe a ring or bracelet. There's no need for an abundance of chains, bracelets, and a ring on every finger. A gentleman is modest.

• Knockoff/fake designer brands. A fake Rolex watch or Gucci shirt may seem like a cheap way to look luxurious, but all you're doing is hiding your own insecurities. Just don't.

• Runners/trainers. Unless your first date is at the gym, keep the runners/trainers only for workouts. They look sloppy. A simple pair of dress shoes or canvas shoes is an easy addition to anyone's wardrobe.

• Muscle tee shirts or shirts with low cut V-necks. It doesn't matter how much you work out; it will look unappealing on a first date. Consider a short-sleeved polo shirt if you really want to show off your muscles.

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