Welcome to this Millennial Gentleman article on the ten things men should never wear on a date. Dating can be a nerve-wracking experience, so it’s imperative that you look your best. However, certain fashion choices are best left at home.

Here are the top ten items that men should avoid wearing on a date:

  1. Baggy or saggy clothing: You want to appear polished and well-groomed, not sloppy and untidy. On a date, wearing loose or saggy clothing can give off a sloppy or untidy impression, which is not the impression you want to make. On a date, it’s important to make an effort with your appearance and demonstrate that you’ve considered your outfit. Fitting and well-tailored clothing can help you appear polished and put-together, which can make a favorable impression on your date. In addition, loose or baggy clothing can be uncomfortable and make it difficult to move or sit, which can be distracting during a date. Wearing clothes that fit well and are comfortable can help you feel confident and at ease, resulting in a more enjoyable and fruitful date.
  2. Shorts: Unless you’re going to the beach or on a hiking date, pants or jeans are the best option. Shorts can appear too casual for a formal or semi-formal occasion, or make a man look like a child rather than an adult. Shorts may not be the most appropriate choice for a romantic dinner date, as they may appear too casual. Depending on the length and design of the shorts, they may not be particularly flattering or fashionable. The wearing of pants or jeans can help you appear more put-together and polished. Ultimately, the decision regarding what to wear on a date will depend on the specific circumstances and the planned activity. Constantly consider the formality of the occasion and the dress code, and select an outfit that is both appropriate and comfortable.
  3. Outdated, stained, or wrinkled clothes: Before a date it is always a good idea to ensure that your clothes are clean, pressed, and in good condition. Untidy clothing can give the impression that a man does not take care of himself or has little self-respect.
  4. Athletic workout clothing: It is best to avoid wearing athletic attire on a date unless you are going to the gym or playing a sport together. It is essential to consider the formality of the event and the dress code, and to select an outfit that is both appropriate and comfortable. Wearing stylish, well-tailored clothing can help you appear polished and put-together, which can make a favorable impression on your date.
  5. T-shirts bearing offensive or controversial designs: It is preferable to avoid clothing that may be divisive or controversial and choose something more neutral. Shirts with comic book characters may give your date the impression that you are a child rather than a mature, responsible adult.
  6. Wearing too much aftershave or cologne: A small amount of fragrance can be pleasant, but do not overdo it. You don’t want to be remembered as someone who smelled artificial or overpowering.
  7. Wearing socks and sandals as footwear: It is imperative to avoid this fashion faux pas at all costs. Not only does it make little sense to wear socks with sandals as your socks will be exposed to the dirt but it makes you look like you just woke up in the morning and are going to get your mail from your mailbox.
  8. Visible underwear: Ensure that your undergarments cannot be seen through your clothing. Visible underwear can be distracting and unattractive, giving the impression of sloppiness or disorder. Additionally, it is considered more polite and respectful to keep one’s underwear concealed and out of sight. Exhibiting your underwear to a date can make you appear impolite and vulgar.
  9. Garments with prominent corporate logos and branding: You should appear confident and fashionable, and not like a walking advertisement for a company.
  10. Clothing with cartoon or comic book characters on it: While you might be a big fan of Marvel or DC comics, or really like to wear anime t-shirts, these are clothing no-no’s on a date if you want to be taken seriously and viewed as a mature adult. Don’t dress like a boy if you want to score with a beautiful woman.

Keep in mind that the secret to looking great on a date is to be well-groomed, comfortable and put together. You’ll be well on your way to a successful and stylish date if you avoid these ten fashion mistakes.

If you are looking for advice on what you should wear to a date, check out these excellent Millennial Gentleman articles we’ve already published,


Carey Martell is Editor in Chief for The Millennial Gentleman. A thirty something modern man who is politically independent, non-religious but a firm believer in ideals of chivalry and traditional family values. Carey lives his life as a vagabond digital nomad traveling and living life to the fullest while managing his businesses remotely with a laptop and internet hotspot connection.