First Date Conundrum: What Should You Wear?

You might not think it sometimes, but it turns out that women are drawn to men who look healthy and attractive, according to Art Of Manliness. Because of this, it’s a good idea to think carefully about what you’re wearing and how well groomed you are, especially before a first date.

First thing’s first: when going on a first date, it’s a good idea to actually dress like a man. That doesn’t mean going to your wardrobe and putting on a bunch of clothes you wore when you were a teenager: it means putting clothes on that gets a woman to take you seriously.

Why is dressing well so important? There are many reasons. The most important and the most obvious when it comes to romantic relationships is the fact that better clothes are more attractive. Since clothes cover more than 90 percent of your body, it’s a good idea to choose clothing that accentuates your positive features while hiding those that aren’t so attractive.

But mere appearances aren’t the only reason why clothes are so important. There’s an argument to be made that dressing right puts you in the right frame of mind. It’s a little bit like wearing a uniform at work: wearing your best date night clothes helps you to focus on the task at hand.

Dressing smart is also a good idea because it shows that you have well-developed social skills. Yes, it would be nice if the world operated on a more philosophical basis, evaluating people’s characters rather than their clothing – but life’s too short for everybody to discover everything there is to learn about your soul. Wearing great clothes is a sign that you understand this, and that you also respect the time of your date.

Finally, it’s worth pointing out that wearing the right clothes can emphasize health, masculine traits. Sports jackets, for instance, are great and making men appear more muscular. Square lines are good for making your face appear broader and the shoulders wider. According to Art Of Manliness, these are features that women are unconsciously attracted to and are a sign that a man has a healthy level of testosterone. Just as men can spot a fertile woman from a mile off, thanks to the way she walks and moves her hips, women can spot a healthy man by the way he moves his shoulders and torso.

So, with that said, what should you wear?

Casual Dates

Even if you’re going on a casual date, it’s still a good idea to wear a smart outfit. Stay away from clothes that look old or dated: you want to give the impression to your date that you’ve made an effort. That means no pale blue jeans, sports clothes that don’t fit, or workwear.

A better combination is dark jeans with a collared shirt. If you have a dress shirt, make sure that you tuck it in, and pair your outfit with a stylish belt that matches your shoes. Always go with leather-style on your first date, and leave your smelly gym trainers at home.

Dinner Dates

For men who live in urban areas, jackets are a must on dinner dates. You don’t necessarily have to wear a suit jacket, but some kind of blazer jacket is essential. Jackets tend to be very flattering on the male form, emphasizing the shoulders and slimming the waist. If your meal is in the daytime, consider wearing something a little more casual, like a sports jacket. Remember, science has shown that jackets make men appear more authoritative and masculine, which are important unconscious signals that a first date will pick up on.

Jackets are great for another reason too: their ability to hold and carry all your first date supplies.

Pay Particular Attention To Your Shoes

Most men think that their choice of shoes isn’t all that important on date night – after all, they spend most of their time hidden away under the table. But it turns out that shoes are actually very important, communicating things like social status and personality type. The impression she will get from canvas sneakers will be very different to the impression she will get from dress loafers.

Wear Stylish Accessories

Stylish accessories, like Men’s Gold Chains by Frost NYC, pocket squares and cuff links are in vogue right now. So too are watches and other high-quality jewelry. Accessories are important because they communicate the fact that you are a man who is interested in all the small details.

It’s worth remembering, however, that wearing jewelry as a man is a balancing act and one that is tough to get right. Don’t choose to wear anything that doesn’t sit right with your personality. If wearing a big, gold-encrusted watch doesn’t feel right, skip it.


A good rule of thumb is never to get your haircut in a different style right before a first date. The woman who agreed to go on a date with you chose to do so because of the way you looked when you first met, so she will be expecting you to turn up with the same barnet that attracted her in the first place.

Stick with your regular grooming routine, style your hair in the same way, and leave it as that. If you must, get your hair trimmed, but remember to go to your usual barber, and not somebody else. Also, check out some of the numerous articles online for how to style your hair and what hair products to use.

All The Little Details

On a first date, you want to look your best. That means paying attention to all those little grooming details you’d usually ignore. Things like making sure your nose hairs aren’t sticking an inch out of your nostrils and making sure that your fingernails are trimmed. These details are an important signal that you take care of your body and you are thinking about the woman you are dating. Of course, nobody is suggesting getting your chest hair waxed off: that’d be a little extreme. Small grooming details are important for when a woman gets closer to you.

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