What To Wear On The First Date For Guys

what to wear on the first date for guys

So, you’ve scored yourself a first date with your crush. Congratulations! In an ideal world, trivial matters like what you’re wearing shouldn’t matter but let’s be real, first impressions do matter and what you wear can say a lot about you in the eyes of your date.

Deciding what to wear on the first date for guys can almost be as nerve wracking as going on the date itself, but choosing the right outfit can help boost your confidence and improve your chances of a perfect first date. Even if you’re not one to stray from your everyday jeans and T-shirt, there are simple and effortless ways to dress comfortably and fashionably for any day or night date activities.

What to Wear on the First Date for Guys

Choosing the perfect outfit for a first date involves striking the right balance between looking well-groomed, handsome, and feeling comfortable. The key is to showcase your personal style while being mindful of the venue and activity for your date. Here are some versatile options for what to wear on a first date for guys for any occasion.

First Date Outfits for Men

Casual Coffee or Drinks

what to wear on the first date for guys

For a relaxed coffee or quiet bar date, go for a smart-casual look. Pair well-fitted dark jeans with a crisp button-down shirt, polo shirt, or fitted sweater. Throw on a leather jacket for an extra touch of cool. Complete the look with clean sneakers or loafers and subtle jewelry like a ring and a watch.

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Classic Dinner Date

what to wear on the first date for guys

When heading out for a classic dinner date, you can never go wrong with a fitted sports blazer in a neutral color, such as navy or charcoal, a crisp button-down shirt, thin tie, and well-fitted trousers or dark jeans. Elevate the look with polished leather shoes and stylish accessories like subtle jewelry and a classic watch. 

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Cinematic Date Night

what to wear on the first date for guys

For a night at the movies, aim for a comfortable, casual, yet stylish outfit. A pair of stylish jeans paired with a well-fitted sweater or a fitted polo shirt strike the perfect balance between laid-back and put-together. Accessorize with minimal jewelry and a stylish bag and wear clean sneakers or loafers to finish the look.

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Indoor Date Night Escape

what to wear on the first date for guys

If you and your date are planning a quiet night of cooking dinner and watching movies, you should prioritize comfort, while still making a good impression. A fitted T-shirt, polo, or sweater paired with jeans or fitted joggers can keep you comfy during cuddle sessions while still looking presentable for your date. Finish the look with a stylish pair of sneakers or slip-on shoes like Hey Dudes, and don’t forget the clean socks!

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Outdoor Adventure Date

what to wear on the first date for guys

For a date that involves cool weather activity or the great outdoors, you may prioritize keeping warm but that doesn’t mean sacrificing style. Choose well-fitted chinos or durable cargo pants paired with a thermal sweater or winter vest. Throw on a stylish puffer jacket or parka along with the usual winter essentials: insulated boots, a beanie, scarf, and gloves.

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Outdoor Concert or Event

what to wear on the first date for guys

If your date night involves an outdoor concert or event, wear a simple T-shirt, possibly adorned with your favorite band’s logo, or a tank top paired with slim-fit jeans, hoochie daddy shorts, or chinos. Complete the look with comfortable sneakers or sandals that will withstand long hours of standing and dancing and accessories like an anklet or fedora hat.

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What NOT to Wear on a First Date for Guys

what to wear on the first date for guys

While it’s crucial to express your personality through your clothing choices, there are certain items that are best left in the closet on a first date. Avoid these fashion faux pas to ensure your date focuses on your charm rather than your wardrobe missteps:

Overly Casual Attire:
While comfort is essential, showing up in overly casual or sloppy attire can send the wrong message. Leave the baggy sweatpants and graphic T-shirts for lazy Sundays at home. Aim for a polished yet relaxed look that shows you’ve put thought into your appearance and put a little effort into impressing your date.

Logos and Slogans:
Clothing covered in logos or loud slogans can be distracting and give off a juvenile vibe. Keep it classy by choosing pieces with subtle branding or opting for clean, logo-free attire. Let your personality shine through your conversation, not what brand you’re wearing.

Ill-fitting Clothes:
One of the quickest ways to undermine a great outfit is by wearing ill-fitting clothes. Whether it’s a baggy suit, too-tight jeans, or an oversized shirt, make sure your clothing fits your body properly. Nothing will make you feel more awkward than having to constantly adjust your clothes every few minutes.

Old or Worn-Out Clothing:
Wearing clothing that shows signs of excessive wear, fading, or pilling can inadvertently communicate a lack of attention to detail. While comfort is crucial, avoid wearing your 10 year old favorite shirt and aim for clothing that is fresh and well-maintained. You don’t need to jump on every latest trend but don’t get caught in clothing that’s clearly old and out of style.

Dirty or Stained Clothes:
Nothing will turn your date off quicker than visible stains or dirt. Whether it’s remnants of yesterday’s lunch or a coffee spill, arriving on a date with dirty clothing can send the wrong message, that you just don’t care. Before heading out, take a moment to inspect your outfit for any stains or marks. A clean appearance not only reflects personal hygiene but also shows your commitment to presenting the best version of yourself and the desire to impress your date.

Too Many Accessories:
While accessories can elevate an outfit, going overboard can be distracting. Avoid wearing an excess of jewelry, hats, or other accessories that may make you appear overly adorned. Stick to a few well-chosen pieces to complement your overall look.

Too Strong Cologne:
Just as your clothing can leave a lasting impression, so can the fragrance you choose. While the right cologne can be an enticing addition to your overall presentation, overdoing it can lead to the opposite effect. The goal is for your date to catch a subtle whiff when they’re close, not to suffocate them in a cloud of fragrance that surrounds you. 

Other First Date Tips for Men

what to wear on the first date for guys

Beyond the wardrobe choices, a successful first date is a delicate dance that involves more than just looking good. Here are some additional tips to ensure your first date is memorable for all the right reasons:

  • Be Punctual: Time is a valuable commodity, and punctuality is a sign of respect. Arriving on time not only sets a positive tone for the date but also shows that you are organized and considerate of your date’s time.
  • Mind Your Grooming: Personal grooming goes hand in hand with fashion. Ensure you’re well-groomed, from a clean shave or well-maintained beard to neatly styled hair. Fresh breath is a must, so consider a breath mint or chewing gum before the date.
  • Confidence Is Key: Confidence is attractive, so carry yourself with assurance. Stand tall, make eye contact, and engage in genuine conversation. Remember to smile; it’s a universal sign of warmth and friendliness.
  • Choose the Right Venue: Consider your date’s interests when selecting the venue. Whether it’s a quiet café, a trendy restaurant, or an outdoor activity, choose a setting that allows for easy conversation and aligns with shared interests.
  • Active Listening: Show genuine interest in what your date has to say. Active listening involves not only hearing the words but also understanding the emotions and nuances behind them. This creates a connection and makes the conversation more meaningful.
  • Avoid Controversial Topics: While it’s essential to be yourself, a first date may not be the best time to delve into sensitive or controversial topics. Keep the conversation light, focusing on shared interests, hobbies, and positive experiences.
  • Put Away Your Phone: Nothing says disinterest more than constantly checking your phone during a date. Keep your phone on silent or vibrate, and give your full attention to your date. This shows respect and genuine engagement in the moment.
  • Compliment Sincerely: Compliments can be a great icebreaker, but they should be genuine. Compliment something specific about your date, whether it’s their outfit, smile, or an interesting aspect of their personality. Authenticity goes a long way.
  • Follow the Two-Drink Rule: While a drink or two can help ease nerves, it’s crucial not to overindulge. Stick to the two-drink rule to maintain clarity and ensure you present your best self. Remember, moderation is key.
  • Express Gratitude: At the end of the date, express your gratitude for their company. If you enjoyed the evening and would like to see them again, let them know. Sincerity and openness lay the foundation for future connections.
  • Respect Boundaries: Everyone has different comfort levels when it comes to physical contact. Respect your date’s boundaries and read their cues. If the chemistry is there, a simple goodnight hug or handshake might be appropriate. Always prioritize consent and communication.
  • Follow Up: If you had a great time and would like to see the person again, don’t hesitate to express your interest. A simple text or call thanking them for the date and expressing your desire to meet again can go a long way in solidifying a connection.

Remember, the goal of a first date is to get to know each other and establish a connection. While we’ve dived into the nuances of first date fashion, always remember that the best accessory you can wear is confidence and a fun, relaxed demeanor. Looking good helps you feel good, ensuring a successful and enjoyable night for both.

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Mark Lim

Hey there, I'm Mark Lim! My journey began with a passion for helping people become the best versions of themselves. As a personal trainer and dietician for 10+ years, I've had the privilege of guiding countless individuals on their health journeys. From designing tailored workout routines to curating personalized nutrition plans, I've seen the transformative power of a holistic approach to well-being. I'm an avid reader and love to cook. I try to live my life as natural and clean as possible and am all about the synergy between health, intellect, and style. Traveling is another hobby that I don't get to enjoy enough anymore. I cherish the days of my early 20s backpacking Southeast Asia and hope to explore more countries soon.

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