The location of the date should influence, if not determine, your choice of attire. If your date is choosing the place and tells you it’s a surprise, ask them what they think would be a good outfit choice. That doesn’t mean you have to wear exactly that, but at least you’ll have some idea, so you don’t end up feeling overdressed.
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Smart casual is often the best choice
Smart casual is the best choice for dinner and a movie for both men and women. Fashion doesn’t have to be complicated, yet people fall into the trap of overthinking far too often.
Thinking too much about a clothing item or one particular detail can do a lot of damage. Those new to dating are especially vulnerable, as they tend to ask themselves too many unnecessary questions instead of focusing on the essentials. For men, there is no point in wondering how to match a scarf to a belt or what width belt is best for a pair of raw jeans. And yes, you can wear a trench coat even if you’re under six feet tall.
You’re not alone. Forbes Magazine reports that almost three-fourths (73%) of those aged 25-35 chronically overthink, as do more than half (52%) of people aged 45-55. People who live with persistent anxiety can feel like they are stuck in a negative thought cycle.
Why do we overthink our outfits? There are two main reasons: people don’t always try things on before they buy them, and some anxious daters try too hard to rationalize everything.
Avoid false advertising
In an effort to impress, some people will attempt to stand out with designer clothes and flashy accessories. Peacocking remains highly common among men in 2024, and it even happens subconsciously. The female analogy is going overboard with sexiness. You might be on a date with the wrong person if you feel you need to wear something revealing to hold his attention. Striking a balance is important: wear a long skirt if you choose a low-cut top.
There is nothing wrong with being a jeans-and-a-T-shirt person. Your potential partner is going on a date with you for a reason, and dressing up is false advertising if you don’t normally do it.
The devil is not in the details when it comes to first dates
You don’t need to know details like the thickness of a sneaker sole, the exact shade of white to look for in sneakers, or the crotch size for a pair of jeans. Some men will decide not to buy a pair of jeans just because there’s a crease in the back pocket, even if everything else – the material, the thigh fit, etc. – was perfect. Likewise, there is no need to worry about your belt. Simply choose one you like and let it wear over time. You’ll never wonder what belt to wear with what again.
Wearing a scarf should come naturally and spontaneously, except if a polyester one from the dollar store was your first thought. Don’t stress out over bracelets: a little leather one will work no matter the color. Don’t try to match your shoes to your scarf: it’s the classic overthink.
When in doubt, go for comfort
You might look amazing in a tight-fitting dress, but it’s not the best choice if you’re pulling it down or shifting uncomfortably in your seat all evening. When in doubt, go for comfort. Most people realize the importance of feeling comfortable in their skin. According to a recent fashion survey, 81% make comfort their top priority, ahead of style or price. Only 13% said following the latest fashion was essential.
The same goes for shoes. A woman struggling to walk in hot red platforms is nothing more than an eyesore. What’s more, your sore feet might ruin your mood, and it will affect your date.
Finally, don’t buy an outfit for the first date. If it doesn’t go well, it will feel like a waste of money.
Recap
- Smart casual is often the best choice
- Avoid false advertising
- The devil is not in the details
- When in doubt, go for comfort
