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The Man’s Guide to First Date Outfit

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It can be difficult to choose the right outfit for your first date. While you want to impress her, you don’t want it to seem like you’re trying to hard.

While you want to display a little of your personality, it is important not to let it be too casual.

Don’t worry. You don’t have to be a fashionista. There are many outfits that you can create to impress your lady, no matter your personal style.

The Perfect First Date Outfit

I have asked hundreds of women their top style tips for men. There are some answers that stick out repeatedly.

So you can impress your date, I will break it down piece by piece.

The sections are a good place to start. You can scale up or down depending on the occasion (e.g., going to a bar or meeting with friends). If you are meeting her for a bagel, a tux won’t make her swoon. We won’t know what famous first date you planned so we’ll just start with the basics.

On Top

An Oxford cloth button down (OCBD) is your best bet for a top. You can style it in many different ways. Darker colors are more flattering. A nice button-down shirt in navy or black is a good choice.

You can wear the OCBD with a tee underneath if you are having a casual lunch date. To show off your forearms, roll the sleeves twice. Women find men’s forearms attractive. It is best to do everything you can to free those.

However, you should not casually roll your sleeves when it is freezing outside. You may also want to bulk up your noodle arms before you let the pythons loose.

The shirt roll should be below your elbow.

If you are going out on an evening date, or if you don’t like the layered tee and OCBD look, leave your shirt buttoned. A bomber jacket or simple sweater is great for cooler evenings. If it’s warmer outside, roll your sleeves and stun her using those man-wrists.

If you are a fit and athletic guy, I hope that you haven’t become lazy about your style. Even though you look great in a t-shirt, it’s not necessary to put more effort on a date. This is a big mistake. You can take your game to the next level by wearing something crisp like an oxford shirt with a tucked-in collar. Are you stylish and fit? You’re a total catch.

As you can see, I prefer the button-down shirt in an oxford for almost every first date. Although there are some exceptions, I will cover these later. For now, know that a good OCBD will be your best friend regardless of your body type. It’s stylish and appropriate for almost any occasion.


Your pants or shoes might be the most important thing to wear on a date night. You’d be wrong. Your accessories are more important than you think.

A nice watch is the most popular form of men’s jewelry and one of your best ways to express yourself subtly.

You should choose a watch that is masculine, elegant, and not too common for your date.

The Vincero Outrider is a great choice for casual wear. It measures 40mm in diameter and is not too large. Anything larger than 44mm is not recommended. You don’t want your watch to be too large. It can make your wrist look too small or make you appear too busy. However, 40mm strikes the perfect balance of strong and masculine without going too far. I feel the need for me to prove myself to everyone.

A classic automatic such as the Vincero Icon, which is perfect for dressier occasions like a cocktail bar, is a better choice. You’ll be able to show your class with a stylish, refined dial and a bracelet made of steel.

The Icon also has a 40mm dial. This makes it a flattering size. Silver accents draw her attention to your hands, forearms and hands, which are two areas that women love.

The Vincero Icon makes a statement. It comes in a stylish and affordable timepiece that includes the Seiko automatic movement, sapphire glass, and high water resistance. The Icon will prove that Vincero is committed to quality.

Sticking with your personality is the key to accessories. Don’t wear a signet ring that is too bulky if you don’t feel confident in it. You don’t want any of your jewelry to be out of place. A belt that matches your watch and shoes is a sign you are a man who cares about the details.

If you feel the mood, leather bracelets and even a metal wrist can draw attention to your masculine traits without appearing trite.

At the Bottom

Many guys are limited in the number of pants they have to choose from when they start paying attention to style. Although there is a lot to choose from, it may not be apparent if you are just starting your style journey.

On your first date, reach for your crisp jeans with no holes or distressing and in black or indigo. Chinos can be worn up or down depending upon what they are paired with. Jeans are my favorite, but I recommend that you wear your best pair for a first date.

Do not wear your most distressed jeans on your first date. You should instead choose the crisp, deep blue jeans that you may save for Saturday night, even though your date is on a Saturday.

Jeans are casual by nature, so you can wear the most formal pair of jeans and still look casual.

If the date requires it, avoid more casual pieces such as joggers or workout shorts. Workout apparel is appropriate if you met at the gym, and your first date is a post-cycling smoothie. Play it simple, otherwise.

No matter what you do, don’t wear your old cargo shorts. Cargo shorts are horrible, that’s what all women can agree on.

A pair of classic, simple chino shorts is a great option for a hot day with your date.

All bottoms should be fitted. You shouldn’t wear pants that are too loose or too tight. Even for the sexier gents, I recommend a slim fit. It’s amazing how few men understand the basics of fitting clothes properly. Women are envious of those who do.

You can show your date you have control over at least one aspect by wearing pants that fit well. She’ll love it. You should understand style and dress well.

On the feet

Your shoes are the key to bringing your entire outfit together. A study found that 64% of women judge men’s shoes. You can be sure she will check out your shoes on their first date. This is the most difficult part because your footwear will determine the formality of your style.

Think about it: If you wear a top and bottom that are oxford, chinos and dress shoes, it might seem like you have just finished your workday and are taking a break from the office. You can make the same top and bottom look sophisticated, chic, and polished by pairing it with white sneakers.

If I was forced to choose between two pairs of shoes for 100 first dates, and I could only afford one pair of shoes, I would opt for a white dress sneaker with brown city boots.

For any daytime date, you can wear your white dress shoes. You can match them with any color combination you have, and if they are kept clean, it shows that you care about the things in your world.

A pair of well-maintained brown boots can be a great choice for any evening date. Boots look great with jeans or chinos and, like white sneakers.

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