As a menswear fashion designer, I frequently get asked, “What should I wear on a date?” I also work with a lot of matchmakers in the metro Phoenix area, and they send me their clients to help them create their dating wardrobe outfits. However, before we get into the topic, I need to have a little chat with the men who are reading my blog as well as their partners who often help them choose their clothes. “Guys, I know you want to show up in your favorite sports jersey and cargo shorts, but if you want to attract a woman who is beautiful, who does her hair, who tries to look her best, you can’t show up looking like a troll wearing a backwards baseball hat. You need to make a good first impression and that takes effort, especially on the first date.”
In the beginning, you must look like you care. You don’t have to show up in a three-piece suit. You don’t have to spend a bunch on a fancy watch or expensive clothes. You just have to look pulled together. What do I mean by that?
Small things that take a little effort go a long way, and women and men notice.
Now let’s get into the topic and talk about what to wear on dates. First, if you want to look a little dressier, darker colors are your best choice. The key thing is to keep it simple. For example, pairing a basic polo and dark colored slacks, is a great way to look more polished and sophisticated, and don’t forget your accessories to finish the look. They should include a dark belt and dark shoes.
Now, let’s talk a little bit about a more casual look. For example, let’s say on a first date, you’re going to play miniature golf, or bowling, or you’re going on a picnic, or a walk in the park, etc. You can still wear a nice polo shirt with a little bit of color or with details on it. The bottom line here is that it doesn’t scream your college sports team or some crazy golf style.
You might think this isn’t important, but clothing like the examples above will make your date focus more on your clothing than your face or what you’re saying because it creates a big distraction — from you. And again, tuck your shirt in. You can pair it with dressy shorts, and I carry them at Q Contrary, or you can can always wear it with something more fun like a good pair of colored jeans or colored pants or, even my favorite, khakis (I carry some nice ones.)
As an alternative, you could also wear that dark polo shirt with gray jeans or blue jeans if the date is more casual. Another option is to wear a great short sleeve shirt, again in darker colors with a simple pattern (just a fun casual shirt,) and a nice pair of jeans. This is a look that works for dates to a lot of places — going to brunch, going out with friends, etc.
Lastly, tuck your shirt or polo in, and remember, a collar on the shirt just makes you look like you care a little. Now put a smile on your face, and you’re ready to go. These are looks you can wear for what I call “nice/casual” dates.
Next, what if you want to step it up a little? For example, a really nice dinner at a fancy hotel or something with a great view for cocktails? Let’s say you want to wear a jacket or something just a little bit showier, or maybe with a little more style.
Again, wear a collared shirt and a great jacket that you can pair with blue jeans or darker slacks, the dressier the better. If you do decide to wear a jacket, don’t feel like you must keep the jacket on the whole time. First impressions are always incredibly important so if you show up wearing a jacket and a collared shirt, oh my gosh, she’ll just melt, and if she doesn’t, she’s not your kind of girl.
On the other hand, if the jacket’s too much, but you still want to look polished and presentable, a great look to try is a long sleeve polo shirt or a long sleeve dress shirt that’s tucked in. Put on a belt, a pair of great shoes, and you’re good to go.
As an aside, if you have blue eyes, wear a blue shirt. Your eyes will totally pop, and she or he will just totally melt. It’s a great way to just make those baby blues more dominant.
Now, let’s talk a little bit about a more casual look. For example, let’s say on a first date, you’re going to play miniature golf, or bowling, or you’re going on a picnic, or a walk in the park, etc. You can still wear a nice polo shirt with a little bit of color or with details on it. The bottom line here is that it doesn’t scream your college sports team or some crazy golf style. You might think this isn’t important, but clothing like the examples above will make your date focus more on your clothing than your face or what you’re saying because it creates a big distraction — from you. And again, tuck your shirt in. You can pair it with dressy shorts, and I carry them at Q Contrary, or you can can always wear it with something more fun like a good pair of colored jeans or colored pants or, even my favorite, khakis (I carry some nice ones.)
Again, just make sure your clothing is cleaned and tailored. Don’t forget to wash your hair and face and just keep a smiling. A little effort goes a long way, and your date will notice it. If they don’t, they’re not for you so just move on.
