What To Wear On First Date Men - Style Guide & Tips

First impressions are crucial，especially when it comes to a first date. As a style and grooming writer with a passion for men's fashion, I understand the importance of dressing to impress. In this comprehensive guide，I will help you navigate the world of first date outfits for men, ensuring that you strike the perfect balance between style and comfort.

Before we dive into the specifics，it's important to consider the dress code for your particular venue. Whether it's a casual daytime outing or an elegant evening affair，understanding the appropriate attire can make all the difference.

For daytime first dates，opt for a casual yet stylish ensemble. A well-fitted dress shirt paired with tailored jeans or chinos is always a safe choice. Avoid busy patterns or garish prints that may be distracting. Instead，stick to neutral colors that exude sophistication.

On the other hand，evening first dates call for dapper and sophisticated attire. Consider donning a tailored suit in a classic color such as navy or charcoal gray. Add a touch of personality with a colorful pocket square or printed dress socks.

Of course，knowing what not to wear is just as important as knowing what to wear. Avoid wearing anything too casual or sloppy，such as sweatpants or oversized shirts. Remember，presentation matters and can significantly impact your date's first impression of you.

Accessories can elevate your outfit and showcase your attention to detail. Opt for tasteful accessories such as a stylish watch or a well-chosen tie that complements your outfit. However，be mindful not to overdo it – simplicity is key.

In conclusion, dressing appropriately for a first date is essential in making a positive impression. By following these guidelines and selecting the right outfit for the occasion, you'll exude confidence and charm from the moment you meet your date. So, read on to discover the best first date outfits for men – because looking good is just as important as feeling good.

Understanding the Venue: Dress Code for First Dates

Getting dressed is an action. And, as the saying goes, actions speak louder than words. When it comes to a first date, what you wear can say a lot about you before you even say a word. It's important to dress in a way that shows you care and have made an effort to impress your date. As Morganna，27, puts it，"When a guy dresses like a teenage boy，and it looks like he didn't care at all, it is distracting and really kills the first impression." So，let's make sure you're well-prepared with the right outfit.

The key to dressing appropriately for a first date is understanding the venue and its dress code. Different venues call for different attire, and you want to make sure you blend in while still standing out in a good way. Whether it's a casual daytime outing or an elegant evening affair, your outfit should reflect the occasion.

For daytime first dates at casual venues like coffee shops or outdoor parks, opt for a stylish yet relaxed look. A well-fitted shirt，dark jeans，and clean sneakers will strike the perfect balance between casual and put-together. On the other hand，if you're meeting your date at a fancy restaurant or attending a nighttime event，aim for a more formal attire. A tailored suit, dress shirt, and polished dress shoes will ooze sophistication and charm.

It's important to pay attention to the details of your outfit as well. Ensure that everything is perfectly ironed and free of wrinkles or lint. Leaving just the right amount of buttons open on your shirt adds a touch of allure without going overboard. These small details can make a big difference in how put together you look and feel.

When deciding what to wear on a first date, always consider the time of day and weather. Daytime dates generally call for more casual outfits, while nighttime dates allow for slightly dressier looks. Additionally, think about the activities you'll be engaging in during the date. Dressing appropriately for the location and planned activities shows that you're attentive and considerate.

Common First Date Venues and Appropriate Dress Codes

Casual Coffee Shop: Smart-casual attire is suitable. Opt for a well-fitted shirt, dark jeans, and clean sneakers.
Fancy Restaurant: Dress to impress with a tailored suit，dress shirt, and polished dress shoes.
Outdoor Park: Keep it casual and comfortable with a pair of well-fitting jeans, a stylish t-shirt，and sneakers.
Dive Bar: Go for a relaxed vibe with a fitted button-down shirt, dark jeans，and casual leather shoes.
Museum or Art Gallery: A smart-casual look is ideal. Wear a blazer over a clean shirt paired with chinos and loafers.

Now that we've covered the basics of understanding the venue, let's dive into the specifics of what to wear based on the venue. From casual coffee shops to fancy restaurants, we'll provide you with outfit ideas tailored to each setting. So，stay tuned and get ready to impress on your first date!

Daytime First Date Outfits: Casual but Stylish

When it comes to a first date，one of the most important aspects is what you wear. Your outfit sets the tone and can make a lasting impression. But finding the perfect balance between casual and stylish can be a challenge. That's why I'm here to guide you through the world of first date fashion.

For a daytime first date，you want to go for a casual yet stylish look. Start with a fitted blue henley paired with olive chinos. This combination creates a cohesive look that is both comfortable and fashionable. To complete the ensemble, add a watch and some sunglasses for that extra touch of style. This outfit works well for super casual dates like meeting at the dog park or going for an easy hike.

If you're looking to add some layers to your daytime outfit, consider incorporating a quilted vest instead of a jacket. It provides warmth and interest without the bulk. Pair it with a casual crew neck sweater and skip the tucked-in button-down shirt for a more relaxed vibe.

On hotter days，opt for elevated shorts instead of gym shorts and running shoes. Whether you're sitting outside at a coffee shop or playing mini golf, this outfit strikes the perfect balance between comfort and style.

Pros of Casual Daytime Outfits for First Dates

Comfortable and relaxed look for a casual daytime date
Allows you to express your personal style
Can be easily dressed up or down depending on the date activity
Versatile options that work well for various types of dates
Gives off a friendly and approachable vibe

Cons of Casual Daytime Outfits for First Dates

May not be suitable for more formal or upscale date venues
Could give off a too casual or laid-back impression
Limited options if you prefer a more polished or sophisticated look

But what if the date is in the evening? Let's find out in the next section as we explore dapper and sophisticated evening first date outfits.

Evening First Date Outfits: Dapper and Sophisticated

When it comes to evening first date outfits, the key is to aim for a dapper and sophisticated look that exudes confidence. One classic option is a tailored suit in a neutral color，such as navy or charcoal gray. The crisp lines and impeccable fit of a well-tailored suit instantly elevate your style, making a lasting impression.

Pair your suit with a crisp white dress shirt in a subtle pattern, like a small check or fine stripe. This adds visual interest without overwhelming the overall look. To add an extra touch of sophistication, incorporate a stylish tie in a complementary color that complements your suit and shirt. Whether you go for a solid color or a subtle pattern, the tie can be an opportunity to showcase your personal style.

Evening First Date Outfits: Dapper and Sophisticated

Classic tailored suit in a neutral color, such as navy or charcoal gray
Crisp white dress shirt with a subtle pattern, like a small check or fine stripe
Elevate the look with a stylish tie in a complementary color
Add a pocket square for a touch of sophistication
Finish off the outfit with polished leather dress shoes

Complete the ensemble with a pocket square in a coordinating color or pattern. This small accessory may seem insignificant，but it can make a big impact on your overall appearance, adding that extra flair of elegance.

Finally, don't forget about your footwear. Opt for polished leather dress shoes that match the color of your suit. A well-maintained pair of shoes can elevate any outfit and show attention to detail.

Remember, the goal with evening first date outfits is to present yourself as refined and put-together. By choosing timeless pieces and paying attention to fit and details，you'll create an impression of sophistication and confidence.

Now that we've covered dapper and sophisticated evening first date outfits，let's move on to discussing the things to avoid while choosing your perfect outfit for that special occasion.

What Not to Wear on a First Date

When it comes to choosing a first date outfit, there are certain pitfalls you'll want to avoid. Making the wrong fashion choices can leave a negative impression on your date and hinder your chances of making a meaningful connection. So，let's dive into what not to wear on a first date.

First and foremost, avoid open-toe shoes. While you may have well-groomed toenails, it's best to save them from being seen on a first date. Opt for stylish alternatives like driving loafers or moccasins that add a touch of sophistication without sacrificing comfort.

Hats or sunglasses indoors are also a no-go. Wearing a hat indoors might give the impression that you're trying to hide something，such as hair loss. Sunglasses can make you appear closed-off and unapproachable in social settings. Save these accessories for outdoor activities and remove them once inside.

Ties, although considered formal, can feel stuffy and serious for a first date. Instead, opt for a simple tailored suit paired with a dress shirt to strike the right balance between elegance and comfort.

Graphic t-shirts should be avoided as well. While you may want to express your interests, save those conversations for later dates. Unless you're attending a concert，consider pairing the t-shirt with an unzipped jacket to tone down the casualness.

Sandals are another item to steer clear of unless you're meeting at a pool, beach，or embarking on a hiking adventure where navigating water is expected.

Hoodies and sweatpants are too casual and sloppy for a first date. Instead, opt for less-casual sweaters like cotton pullovers or wool crew necks. For colder weather，choose thick cotton chinos or heavier jeans for a more polished look.

Finally, when it comes to jewelry, avoid anything deliberately worn for work or anything overly showy. Keep things understated and classic on a first date to allow your personality and conversation to shine.

By avoiding these fashion blunders，you'll present yourself in a confident and put-together manner, creating a positive first impression. Remember, it's not just about what you wear，but how you wear it. So, dress to impress and let your charm do the rest.

Finally，let's wrap up with some key takeaways: Avoid open-toe shoes，hats and sunglasses indoors，ties，graphic t-shirts，sandals，hoodies, sweatpants, and jewelry deliberately worn for work or overly showy. Dress to impress and be confident in your choice of attire, and you'll leave a memorable first impression.

Choosing the Right Accessories

Accessories play a crucial role in completing your first date outfit and elevating your overall look. They not only showcase your attention to detail but also allow you to express your personality. The right accessories can make a significant impact on the impression you leave on your date.

When it comes to accessories, it's important to stick with what aligns with your personal style and makes you feel comfortable. Avoid wearing anything that looks out of place or feels unnatural to you. One accessory that never fails to impress is a well-chosen belt. Opt for a belt that matches the color of your shoes and watch，as this demonstrates your keen eye for coordination. If you're looking to add an extra touch of masculinity without overpowering the outfit, consider leather bracelets or metal cuffs.

These subtle accessories draw attention to your masculine attributes without appearing misplaced. Additionally, wearing a stylish watch that reflects your personality is a classic choice for men's accessories. Choose one that is masculine, stylish，and slightly unique to make a statement.

Accessories for a Memorable First Date

A stylish watch that reflects your personality
A well-fitted belt that matches the color of your shoes
Leather bracelets or metal cuffs to add a touch of masculinity
Sunglasses for daytime outdoor dates (remove them when chatting)
Scarves to keep warm in winter and add a spice to your outfit
Hats for functional purposes like afternoon park dates (avoid if trying to hide hair loss)
Avoid bringing bags unless necessary，as they can make you look childish
Consider investing in quality clothes and getting them tailored for a confident look
Ensure your shoes and accessories are clean and well-maintained for a better impression
An oxford button-down shirt is versatile and appropriate for most date situations
A wristwatch is a commonly accepted form of men's jewelry, choose one that is masculine，stylish，and unique
Bracelets like simple metal cuffs or chains can add subtle elegance to your appearance
Avoid wearing hats unless they serve a functional purpose outdoors
For fall and winter dates, opt for outfits that provide warmth without compromising style
If meeting someone after work，dress in a 'fun' version of your office attire with colorful accents
Accessories are an excellent way to express yourself and initiate conversations on a first date

For daytime outdoor dates，don't forget about sunglasses. They not only protect your eyes but also add a cool factor to your overall look. Just remember to remove them once you sit down to chat and maintain eye contact.

When it comes to scarves, they can be a great addition during colder months, adding both functionality and style to your outfit. However, only wear a scarf if the weather calls for it, as wearing one unnecessarily can look forced.

Hats can serve a functional purpose，such as keeping warm or shading your eyes from the sun during afternoon park dates. However, unless there's a specific need for it，it's best to skip wearing a hat on a first date.

Avoid bringing bags unless necessary, as they can give off a more casual or childish vibe. Toting around work bags on a dinner date may also signal a lack of boundaries.

Remember that cleanliness is crucial when it comes to accessories. Ensure that your shoes, especially white sneakers, are spotlessly clean. Minor details like these may not be consciously noticed right away, but they add up to create a better overall impression.

To truly stand out from the crowd，consider investing in quality clothing and getting them tailored to your body. The confidence gained from wearing well-fitted clothes is unmatched and sets you apart from the rest.

As we wrap up this section on accessories, keep in mind that they provide an excellent opportunity for conversation starters during a first date. Express yourself and let your accessories add interest and intrigue to your outfit.

Let's see how to wrap up everything for a successful first date outfit.

Wrapping Up: First Date Outfit Essentials

When it comes to a first date, the perfect outfit can make a lasting impression. But what should you wear? The truth is, there's no one-size-fits-all answer. It all depends on your personal style and the type of date you have planned. However，there are some essential elements that can help you create an impressive first date outfit.

Start with a plain，casual button-down shirt. This versatile piece can be styled in various ways and is suitable for both daytime and nighttime dates. Pair it with nice dark jeans for a polished yet relaxed look. Simple white sneakers complete the ensemble，adding a touch of modernity.

For more casual daytime dates, consider adding a good henley or some well-fitting t-shirts to your wardrobe. A bomber jacket can also elevate your outfit without sacrificing comfort.

If you're going for a more refined look on an evening date，opt for a tailored suit in a neutral color like navy or charcoal gray. Pair it with a crisp white dress shirt and a stylish tie. Don't forget to add a pocket square for that extra touch of sophistication.

Remember，confidence is key when it comes to dressing for your first date. Wear clothes that fit well and pay attention to the details，such as ironing out wrinkles and polishing your shoes. And most importantly, choose an outfit that reflects your personal style and makes you feel comfortable and confident.

Now that you have the essential first date outfit ideas, go ahead and dress confidently for your special occasion!

Frequently Asked Questions

What is the best color to wear on a first date?

When it comes to choosing the best color to wear on a first date, it's all about creating a positive impression while staying true to your personal style. Dark or neutral colors，such as navy, gray, white, and black, are safe choices that lend a sense of sophistication and versatility to your outfit. These understated hues allow the focus to be on you and the conversation rather than what you're wearing.

Remember，for daytime dates，you have a bit more flexibility in terms of colors and washes，so feel free to have a little more fun with your outfit choices. Just keep it tasteful and avoid going overboard. And don't underestimate the importance of quality underwear – invest in a nice pair of neutral boxer briefs that fit perfectly to ensure comfort and confidence throughout your date.

Should I wear a suit on a first date?

Wearing a suit on a first date can be appropriate in certain situations，but it's important to consider the venue and overall vibe of the date. If you're meeting at a fancy restaurant or attending a formal event, a suit can make you look polished and sophisticated. However，for more casual daytime dates, a suit might be overkill and make you appear overdressed. It's essential to strike the right balance between dressing appropriately and feeling comfortable in your outfit.