Lets get this out of the way first. Most men don’t know how to dress. Add to that, most women don’t either. So, since you have two groups who are largely unaware that they are not stylish, the odds are your date will be happy with the way you dress.
Style Guide: Dressing Right for Your Date
The Harsh Truth: Most People Can't Dress
Let’s get this out of the way first—most men don’t know how to dress. To add to that, most women don’t either. Since both groups are largely unaware of their lack of style, the odds are that your date will be happy with the way you dress, as long as you put in a little effort.
Most men don’t care what a woman wears as long as she is gorgeous. She could be draped in a potato sack, and it wouldn’t matter. As long as he looks good, everything else can be fixed later. This may apply to women as well, but that’s a debate for another time and perspective.
The key takeaway here is that dressing well is not just about impressing others. When you put effort into your outfit, it can show your confidence as well as personality. A personality that is natural, and not forced. A well dressed person always has a little edge, and that’s half the battle won on your date before it even started.
The Airport Experiment: Proof That Fashion is Lost
If you ever doubt that most people can’t dress, try the airport experiment. While waiting for a long flight, observe people of all ages, genders, and backgrounds. Some dress to impress (why?), while others simply exist in their natural state. It becomes evident that the majority are lost in the fashion wilderness.
That said, fashion is overrated. There are only so many ways to reinvent a pair of pants. Unless we introduce hover pants in George Jetson’s era, fashion will remain a cycle of minor tweaks to the same ideas.
I still don't know if people prioritize comfort over style. If you do this it can lead to a bad mistake - or what we call lazy fashion choices. I once heard a mate complain that a girl was not impressed with him on his date. I said show me your pics. He showed me his “attire” on his date - he was wearing a straw hat! He thought this made him look “cool”. Yeah, I told him, if you were at a hay hoedown barn raising dance.
The trick is to try to balance both—find clothing that makes you comfortable and works stylish as well.
Dressing Right
So, you’ve found your date. Now, what should you wear? Here are some essential pointers to ensure you make the right impression and avoid raising eyebrows with outdated or ill-fitting attire.
PS: I hate when older men wear jeans. You cannot look good in them. Don’t even try it.
First impressions matter, and your outfit is a major part of that. The right clothing can set the beat for your entire date. Think of your outfit as an investment—something that will pay off in how you are seen. The goal is to look good and most importantly age-appropriate!
Getting Fashion-Ready for Your Date
The Basics of Dressing Well
Dressing for a date is tricky. Factors like sex and venue can and should
influence what you wear. Women generally have more options when it comes to dressing up or down. Men are definitely more limited in what they wear. There are only so many variations of pants a man can wear—unless, of course, you want to bring back parachute pants, in which case, I rest my case.
Rule #1: Dress to Impress
This is always the best rule of thumb. Show that you care about your appearance. Second, make it look good - now that is a bit tougher and the key to success. What qualifies as “good taste” will depend on you and that’s where the mistake can lie.
Lets not forget of course - that there are the rare individuals who can wear a potato sack and still look gorgeous—if you’re in that 0.001%, feel free to ignore this advice.
Now - There are two main approaches to dressing to impress:
The Effortless Casual Look: Dress well without making it obvious that you’re trying too hard. This is the best but the hardest. Discuss later.
The Peacock Effect (Done Right): Dressing to stand out. I hate this. Peacocks go home. This usually means loud clothes with oversized brand names that say look at me. It only says you are a douchebag! Remember people, details matter. Make sure your clothes are ironed, your shoes are clean and new, and no pants that don't fit. Small little things like this are the cornerstone of looking good.
Matching Your Wardrobe to the Occasion
Your attire must fit the setting. Avoid the commoner mistakes like dressing too young for your age or choosing inappropriate clothing for your date. We have all seen this happen a million times. Remember, wear clothes that make you feel comfortable. No - not your track outfit but something you feel comfortable in the setting you are going to. If you don’t know it - then google it.
Remember - no one is perfect - you need to hit a home run - a solid double on your first date is a good night. Even high-end fashion brands make mistakes, forcing celebrities into outfits that leave people wondering, “Who let them wear that?”
Another important rule to fashion success is understanding the color they tell you. My rule of thumb is don't understand them! Look in the mirror and see what works. You would be surprised at the strange color combos that actually works! Each person is different - so just stand in the mirror and see what works. If all else fails, look online at a digital fashion magazine and copy what you see in front of you.
If You Have No Style, Do This
Don’t hire a stylist—they often get it wrong. Instead, follow this simple trick:
- Write down three fashion brands or stores you like.
- Visit their websites and see what the male models are wearing.
- Copy the style and color scheme (not necessarily the exact outfit).
This method ensures that you look good without requiring anyone's opinion.
Remember, fashion changes but good taste does not. Once you find a particular look that works for you, stick with it. Give it some variation, dress it up or down - but you will figure out what works simply on your date's replies. (Although if your date's style stinks you're up a river without a canoe people!)
Watches and Things
Some men, or even most men, love watches. They especially love to show off their expensive watches. Part of the masculine formula to show taste and I’ve made it. Yes, you can wear it, but remember, the way you wear it does matter on your date.
How Not to Wear a Watch:
- Don’t let it dangle loosely like a potato bag.
- Don’t make a show of it every time you take a drink or a bite.
- Don’t constantly flash it as if begging for attention.
I know for a fact, no one wants to be bombarded with your wrist moving your watch around as if you're dangling for a compliment or a fish. No need to show it off. It’s there. If they notice fine - if they don’t fine as well. Accessories should be part of your style, but not YOUR STYLE! The key is the often used phrase less is more. Take this to your fashion grave.
Conclusion
There you have it, male fashionistas—a quick and effective guide to dressing well for your date. Follow these tips, and you’ll be on your way to making a solid impression. That’s all we want - solid, if it goes better, and even greater for you. You do not want to go for the home run on the first date - because you run the risk of blowing it - and we do not want that. We just want another date.
Stay stylish, it will make you confident, and most importantly, dress your age!
Updated February 10, 2025