11 Tips for Wearing a Hat on a Date: No Ghosting

Dating hats, Wearing a Hat on a Date, What Hat to wear -

11 Tips for Wearing a Hat on a Date: No Ghosting

Making a good, lasting impression is critical when it comes to dating. But is wearing a hat on a date the right impression to leave? 

For some, hats can be the perfect accessory to elevate your look and confidence, so let's dive into this matter and work out how to rock that hat without the risk of being ghosted.

Follow our guide or remain single. The choice is yours. 

Should I be wearing a hat on a date?

Wearing a hat on a date isn't just a fashion-focused decision; it's also about the message you send to the other half.

Your outfit says volumes about your personality, confidence, and style. 

We must first determine context to understand whether you should wear a hat on a date. 

Wearing a hat is appropriate in most informal settings but not formal places like fancy restaurants. 

Consider your date's opinion, too, as some would find it rude, while others wouldn't bat an eye. 

For some, hats can improve a look, increase your confidence and enhance the dating experience, but each setting, person and date is unique. 

Lets explore further...


1.Should I wear a hat on my first date?

Wearing a hat on a first date can be a bold statement. It shows that you're confident and unafraid to stand out and suggest you are comfortable with your own decisions. 

However, choosing the right hat that complements your outfit and the date's ambience is the difference between building a winning date outfit and one that may leave you single. 

Pro Tip: Opt for classic styles like vintage cord ball caps or ribbed thin beanies. These hats boast a classic look and fit and are incredibly versatile, making them great for a first date. 

2.Can I wear a hat on a second date?

By the second date, you've already made a positive impression. Wearing a hat can continue to showcase your fashion-focused approach. 

However, similar to the first date, be mindful of the context. If your second date is at a formal restaurant, a hat may not be suitable. 

On the other hand, a casual outing can be an excellent choice.

But don't worry. Later in the article, we will look at where hats can be worn on dates. 

3.What do girls think of guys wearing hats on dates?

Everyone's different. Opinions on this vary, but many women appreciate a well-chosen hat on a date. It can make you appear confident and relaxed.

However, ensuring your hat complements your overall outfit and the date's setting is key.

Our Tip: Opt for a hat that's limited, well-made made and creative. We recommend the uniquely designed SLxCHN ball cap, made from premium grey suede and unlike any other cap online. 

 It's undoubtedly geared up to be a conversation starter.


4.Is it rude to wear a hat on a date?

Wearing a hat on a date isn't necessarily rude, but context does matter. 

While In formal settings, like a fancy restaurant, removing your hat is polite. However, in casual settings like a coffee shop or when outdoors, it's perfectly acceptable to rock a cap or a beanie.

Checking with your date is always a good approach as each individual feels differently and impressions, especially 1st ones count!

Our tip: Be attentive to your date's comfort and the ambience to gauge whether wearing a hat indoors is appropriate. Be bold and ask them if they are comfortable with you wearing a hat, too.

It shows you care.


5.The best types of hats to wear

Choosing the right hat is crucial. Classic styles like beanies and baseball caps are popular choices. However, matching the hat with your outfit and the date setting is essential.

6.Boosting confidence: How a hat can help your dating

For some, wearing a hat can be a confidence booster, especially when dealing with insecurities like balding. 

A well-chosen hat can enhance your overall look and provide that extra layer of self-assuredness.

Our Tip: Experiment with different hat styles until you find the one that makes you feel the most confident.

7.Taking your hat off when on a date.

Taking off a hat doesn't often end well, especially if you are using it as a sneaky little shield, hiding that hairline or the fact that you didn't feel like styling your hair.

When the hat comes off, it's like a mini-reveal, showing a side of you that might not have wanted to highlight, leaving you feeling kind of exposed.

Beyond that, you could be left with some notorious 'hat hair' - that flat, messy look no product can fix when trying to impress.

Hat hair will undoubtedly knock your confidence and rhythm, something your date wouldn't appreciate when trying to connect and have a good time.

In dating, it's all about feeling comfortable while looking your best, and sometimes, the hat-off moment can be tricky.

So, we advise wearing headwear only if it remains on for the entirety of the date.


8.Hats on Dates: Casual vs. Formal

Consider the date's setting when deciding to wear a hat. Casual settings like picnics, coffee shops, or outdoor activities are ideal for hat-wearing. On the other hand, formal venues like high-end restaurants may ask you to remove your hat when indoors.

Where is it appropriate to wear a hat?

Appropriate Places to Wear Hats on Dates:

  1. Casual Cafes: When you and your date opt for a coffee date at a casual cafe, donning a hat can give your outfit a relaxed and casual look.
  2. Outdoor Adventures: Whether it's a hike in the woods, a bike ride, or a day at the beach, hats are perfect for outdoor date activities. They offer sun protection and contribute to a sporty look. (no one looks good burnt!)
  3. Picnics in the Park: Enjoying a picnic date in the park? A hat can shield you from the sun's rays while you relax on the grass.
  4. Amusement Parks: When spending the day at an amusement park with your date, a hat can help keep your hair in order, especially on roller coasters. (Make sure you hold onto it!) 
  5. Casual Dining: Opting for a laid-back dinner at a pizzeria, burger joint, or sushi bar? Wearing a hat can add a slice of individuality to your outfit.


Inappropriate places to wear hats on dates:

  1. Fine Dining Restaurants: If you're treating your date to a fancy dinner at an upscale restaurant, removing your hat upon entering is considered proper etiquette. Hats indoors at fine dining establishments can be seen as disrespectful.
  2. Theatre Nights: Planning a night at the theatre or a musical performance? Many theatres have a dress code that requires hat removal indoors.
  3. Dinner with the Parents: If you're meeting your date's parents for the first time, it's best to keep your hat off throughout the evening to avoid giving off the wrong impression. 


9.The perfect hat choices for dates. 

Choosing the right hat is vital. Classic styles like beanies and baseball caps are popular choices. However, matching the hat with your outfit and the date's setting is crucial.

10.Seasonal Considerations when wearing a hat to date. 

Summer Dates: Opt for lightweight and breathable hats for outdoor summer dates. They provide sun protection while keeping you stylish without the nasty sweat stains and smells. 

Winter Dates: In colder weather, knit ribbed beanies and skullys keep you warm and elevate your winter outfits. Consider matching them with your coat or scarf.


Transitional Seasons: During spring and fall, wear versatile hats like the classic cord ball cap, made from a timeless material that's the perfect weight and fit for those in-between months!  

11.Matching your hat with your date outfit

Casual Dates: For laid-back coffee dates or walks in the park, a classic ball cap or a neutral beanie can complement your everyday attire. 

Keep it simple and comfortable. Our Vintage brown cord ball cap would do the job perfectly. 

Dinner Dates: For dinner dates or movie nights, select a stylish low-profile cap that's a well-structured hat and matches your formal outfit. Dark grey or black hats often work well.

Creative Dates: When planning unique outings like art exhibits or live music performances, consider our SL x CHN suede cap. 

It's 3D writing, and distinctive design can be a conversation starter among creatives as a stand-alone piece in fashion right now. 



Your choice of headwear can play a significant role in how you're perceived on dates. 

While some may opt for the hatless route, wearing a hat can be a unique and excellent choice that sets you apart from the competition.

By following these tips and being mindful of the context, you can confidently wear a hat on a date and leave a lasting impression. 

So, embrace your style, whether it's a vintage cord ball cap, a ribbed thin beanie, or a CHN suede cap with 3D writing. Remember, it's not just a hat; it's a statement.

Pro Tip: Explore our Urban Headwear Collection to discover a wide range of hat styles and colours that can elevate your dating game.