What to Wear on a First Date: 5 Looks That Always Impress
One of the scariest things about meeting someone new is trying to plan out what to wear on a first date. It can feel like a real minefield, especially if you don’t know your date very well, so you can’t aim to match how dressed-up they’re likely to get. However, we’ve got some classic outfits that can work for lots of occasions, so don’t panic: we’re here to help!
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We wanted to put this article together because we know this can be a weight on the mind of guys going on a first date. After all, clothing shapes the first impression you give off, so you want to get it right. We’re all about helping people overcome their worries around dating, so we’re going to break down how you can project an image of your best self even if you’re a little nervous.
What to Wear on a First Date: It’s About Effort
We can’t word this any more effectively than Peter Nguyen from The Essential Man: “effort is the most important thing.” This is true in all aspects of life, and especially so when selecting what to wear on a first date. The effort you put in shows that you’re enthusiastic and want the date to go well.
So, with effort in mind, how can you change the way you dress on a first date? A good mindset is to wear clothes that are clean, neat, and well-fitted. The cleanliness might seem a little obvious, but consider how some of your clothes might be older and faded, or have a messy repair from a rip on the sleeve. While that’s fine for day-to-day wear, it’s not quite fancy enough for a date.
It’s also important to ensure you’re well cleaned up before your date. This goes for the obvious things like having a shower, plus making sure that you shave, brush your teeth, and clip your nails. By making yourself look polished, you project an air of confidence and deliberateness that your date will pick up on.
To steal a metaphor from Nguyen, think about a Dad going to pick up his kids in an old car. If the car is battered and dirty, and he’s fifteen minutes late, then it’s a bad look. If the car’s old but clearly neat, clean, and taken care of, plus he shows up early, then you know he’s a good dad. Apply that philosophy to your date night outfit.
Five Great Choices
While everyone’s personal style is a little different, these are some classic, timeless outfits to help you know what to wear on a first date. Pair the philosophy of effort from above with some of these ideas, and you’ll succeed.
Museum: Button down; smart, black jeans; and a light jacket
Walking around a museum is a great getting-to-know-you date, since you can chat about the exhibits as you go. Walking side by side on a date instead of sitting across from each other reduces the pressure of intense eye contact, making it easier to open up and connect naturally. According to relationship psychologist Dr. Terri Orbuch (also known as “The Love Doctor”), “walking side by side helps people feel more relaxed and less interrogated, which promotes more genuine conversation and connection.”
This allows the conversation to flow organically while you both engage with your surroundings, perfect for sparking interesting dialogue without forced small talk.
It’s wise to wear an outfit that appears fairly smart but is still comfortable. Plus, having a jacket gives you some pockets, it’s always gentlemanly to offer to hold something for your date.
Cocktails/Drinks: A well-fitted polo shirt and dress pants
This may seem basic, but the outfit is in the execution. Forget the oversized dress pants and blue polo from your Dad’s wardrobe, we’re aiming a little higher. Track down some slim-fit pants to give you a clean silhouette, and opt for a more daring polo color choice, as long as it matches your coloration.
Dinner: Dress pants, a not-white dress shirt with folded-up sleeves
Knowing what to wear on a first date is a learning curve, and here’s a lesson: going for a full suit is often a little much. Slim-fit dress pants and a smart dress shirt will give you a great base. Build on that by opting for a less boring shirt color than white, and roll up your sleeves a few times to get your forearms out. These are both subtle ways to appear calm and comfortable.
Coffee: Dress pants, a well-fitted tee, and an open suit jacket
The dress pants and jacket make this outfit seem painfully formal. However, as Karlton Miko Tyack, writing for The Modest Man, says, it’s all about balance. By opting for a tailored or slim-fit tee underneath the jacket, you’re keeping things casual enough for a coffee date. If you want to add some height to your appearance have your pants tailored to slightly show off some ankle off, this will give the appearance you are taller than you are.
Mini Golf: Black jeans and a flannel button-down
Our final suggestion on what to wear on a first date is a classic: black jeans and a flannel. The combination is smart enough to appear a little more formal while also being casual enough that it’s comfortable and suitable for a walk in the park or a mini golf date.
Breaking down exactly what you should fill your wardrobe with is complex. Knowing what to wear on a first date, however, can be simple: balance smart neatness with relaxed confidence, and you’re on the right track!
