Common Outfit Mistakes Men Make on a First Date

First dates are significant because they set the foundation for potential relationships. As a result, they can be high-stress for guys who struggle with confidence. Your outfit plays a crucial role in making a good first impression. However, many men make common fashion mistakes that can detract from their appearance and the overall date experience.

And there’s one mistake that men make is both common and hard to recover from:

“They're not dressing like themselves,”
“They're wearing something that they wouldn't normally wear. If they don't wear a suit and tie on a normal basis and they wear it to a date, itt just makes them feel uncomfortable and they just don't feel like their authentic selves.”

- Melissa Slavick, a Taelor stylist

Wearing something unfamiliar as if you are donning a first-date costume is a recipe for dating disaster.

“You want to go in there feeling comfortable wearing something that you're proud of wearing,”

“You want to wear something that shows off your personality, whether it's like a conversational print or just even a color. Wearing something that brings out your personality is what's going to make you feel the best.”
- Melissa Slavick, a Taelor stylist

“Style influences the way you see yourself and the way others see you. When you feel good, others feel that vibe, they feel the energy that you bring,”
- Aisen Li, known as the Asian dating coach

With that said, there’s a limit to how much personality to show. Too much of a good thing is still too much.

“You want to show a little personality and maybe a little flair, but also some tact. You don’t want to look like you're obsessed about fashion all the time,”
- Scott Shapiro, another stylist with Taelor 

1. Overdressing or Underdressing

A prevalent mistake is not matching the outfit to the date’s venue and activity. Overdressing can make you seem out of touch with the setting, while underdressing can give the impression that you don't care.

Overdressing: Showing up in a suit and tie to a casual coffee date or a relaxed park walk can make you look out of place and overly formal. It's essential to gauge the formality of the date and dress accordingly. For example, if you're going to a casual restaurant or a movie, a smart casual outfit, such as a button-down shirt paired with chinos, is appropriate. This demonstrates that you’ve put thought into your appearance without going overboard.

Underdressing: On the flip side, wearing a t-shirt and jeans to a fancy dinner can suggest a lack of effort and respect for the occasion. Aim for a middle ground: opt for a polished yet relaxed look that shows you’ve put thought into your appearance. For instance, a blazer with a nice shirt and well-fitted trousers can work wonders for a dinner date at an upscale restaurant.

2. Ignoring Fit

Two shirts, one is too tight, the other one is too loose

Ill-fitting clothes are one of the biggest fashion faux pas. Clothing that is too tight or too loose can be unflattering and uncomfortable, detracting from your overall look.

Too Tight: Clothes that are too tight can be restrictive and highlight areas you might prefer to downplay. For instance, overly tight shirts can accentuate a stomach or chest in an unflattering way. It's crucial to choose clothes that fit well and allow for comfortable movement. A well-fitted shirt should contour your body without being restrictive.

Too Loose: Baggy clothes can make you look sloppy and unkempt. Ensure your clothes fit well in all areas – shoulders, chest, waist, and length. Tailoring can make a significant difference, turning a decent outfit into a great one. A tailored jacket, for example, can enhance your physique and give you a polished appearance.
(Check out our blog: Dressing for Your Body Type: A Guide for Men / Men’s Size Guide: How to measure your size?)

3. Ignoring the Details

A wrinkled blue shirt and a pair of dirty sneakers

Details can make or break an outfit. Paying attention to small elements shows that you care about your appearance.

Wrinkled Clothes: Wearing wrinkled clothes can give the impression that you don't take care of yourself or that you lack attention to detail. Always ensure your clothes are clean and pressed. Investing in a good iron or a steamer can help keep your clothes looking sharp.

Dirty Shoes: Shoes are often overlooked, but they can significantly impact your overall appearance. Make sure your shoes are clean and in good condition. Polishing leather shoes or wiping down sneakers can make a huge difference. Remember, shoes can speak volumes about your personality and attention to detail.

Inappropriate Accessories: Wearing too many accessories or inappropriate ones can detract from your look. Stick to a few tasteful items like a watch or a simple bracelet. Avoid flashy jewelry or excessive accessories that can be distracting. A sleek watch or a subtle ring can add a touch of sophistication without overwhelming your outfit.

4. Inappropriate Casual Wear

A graphic T-shirt on the left and a man wearing a sport hooded jacket on the right

While casual wear is often appropriate, it needs to be chosen carefully.

Graphic T-Shirts: Graphic tees with bold logos or messages can be distracting and may not convey the best impression. Opt for solid colors or subtle patterns that look more mature and polished. A plain crewneck or V-neck tee can be both stylish and comfortable.

Athleisure Overkill: While comfortable, athleisure can come off as too relaxed for a date. Save the workout gear for the gym and choose something that balances comfort with style. A well-fitted polo shirt or a casual button-down can be a great alternative to gym wear.

5. Ignoring Personal Grooming

Personal grooming is just as important as the clothes you wear.

Unkempt Hair and Beard: Ensure your hair and beard are neatly trimmed and styled. A messy appearance can detract from your overall look. Regular haircuts and beard maintenance can go a long way in enhancing your appearance.

Poor Hygiene: Pay attention to basic hygiene – clean nails, fresh breath, and an appropriate amount of cologne. Overpowering scents can be off-putting, so use fragrance sparingly. A subtle, pleasant scent can leave a lasting positive impression.

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6. Not Dressing for the Weather

Dressing appropriately for the weather shows that you're practical and thoughtful.

Overdressing in Heat: Wearing heavy fabrics or multiple layers in hot weather can make you uncomfortable and sweaty. Opt for lightweight, breathable fabrics like cotton or linen. These materials will keep you cool and comfortable while looking stylish.

Underdressing in Cold: Not wearing enough layers in cold weather can make you appear unprepared. Layering is key – a stylish jacket or coat can add to your look while keeping you warm. Consider a fashionable scarf or hat to complete your winter ensemble.

7. Neglecting to Dress for the Occasion

Every date is different, and your outfit should reflect the nature of the event.

Comedy Club: For a comedy club date , you don’t want to dress too formally or too casually. Aim for smart casual. A well-fitted pair of jeans, a neat shirt, and a casual blazer can be perfect. Avoid trying to dress funny; let the comedians handle the humor.

Outdoor Activities: For a date that involves outdoor activities, practical yet stylish attire is key. Wear comfortable shoes and weather-appropriate clothing. For example, a stylish pair of sneakers and a light jacket can be perfect for a walk in the park or a visit to a farmer’s market.

Sporting Events: If you're going to a baseball game , opt for casual comfort. A well-fitted pair of jeans or chinos, a team-branded shirt, and comfortable shoes work well. Just make sure your outfit is clean and presentable.

8. Not Being Authentic

Lastly, it’s crucial to be authentic in your style. Wear something that reflects your personality and makes you feel confident. Trying too hard to impress by wearing something that doesn’t feel like you can backfire.

Be Yourself: If you're not comfortable in a suit, don’t force it. Instead, find a smart casual look that feels right for you. Confidence is key, and wearing clothes that make you feel good will naturally boost your confidence.

Avoid Trends that Don't Suit You: While it’s good to be aware of current fashion trends, don’t feel pressured to follow them if they don’t suit your style. Stick to classic, timeless pieces that you can feel comfortable and confident in.


First impressions are crucial, and dressing appropriately for a first date can set the tone for a successful encounter. Avoiding common outfit mistakes involves understanding the context of the date, ensuring proper fit and grooming, and paying attention to details. By doing so, you can present yourself confidently and make a positive impression.

Want some help finding nice-looking clothes that will make your date unforgettable? Let Taelor help. Taelor is a menswear rental subscription service dedicated to helping men look their best when it matters most. Our styling service, powered by a human stylist and assisted by artificial intelligence, finds the clothes that help you win – at work, on a date, at a party, or wherever you spend your time.

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