Because I get so many queries from guys about dates, especially first dates, I decided to write an entire article about what to wear on your first date.
This is due to the fact that the first date is the most crucial. There will be no second or third if the first one does not go properly.
As a result, you must go above and beyond on this one.
To get the perfect outfit for your date, you’ll need to do some research on the location.
If you’re going to a park for a picnic, your clothing will be different than if you’re going to a fine dining establishment.
Let’s go over the many outfits that I would recommend for various events.
Table of Contents
Casual Outdoor Date
The first is a casual, enjoyable outdoor date.
If you’re going for a walk in the park, or if you’re going to a sporting event, or if you’re going to buy some food, or if you’re going to a casual coffee shop in the city, this is what you should wear.
The key is to wear something that is both comfortable and highlights your greatest qualities.
For example, a white t-shirt is good, but it must fit you perfectly. It can’t be too loose around the arms and torso. It should appropriately embrace your body to show off your arms and chest.
If you’re going to a sporting event, feel free to represent your favorite team. Just be cautious about how much team clothing you put on. Don’t match the jersey, hat, bracelet, towel, and other accessories.
Pick one or two items and that’s all there is to it.
When it comes to jerseys, be cautious because they might be quite baggy, which does not look good. Make sure it’s the right size for you.
On the bottom, choose slim-fit jeans or chinos, since they will fit you perfectly. You want to look the part if you’re going somewhere trendy.
Slim-fitting skinny jeans will make you appear taller and slimmer.
If you want to wear shorts, go ahead, but please don’t wear cargo shorts. You’ll want to put on a pair of slim shorts that hug your thighs without being too tight.
Never wear basketball shorts on a date unless you’re planning to play basketball.
In terms of footwear, you want something comfy, but it can’t be your worn-in workout sneakers simply because they’re the most comfortable you own.
If you’re heading to the park or a game, wear white shoes.
If you’re headed to a coffee shop, try Chelsea boots. Because most guys will wear sneakers or unattractive trendy shoes. Chelsea boots are a terrific way to stand out from the crowd.
Chelsea boots would certainly catch your date’s eye.
However, just because you’re wearing a t-shirt, pants, and shoes doesn’t mean your outfit is complete. That is only the beginning.
To ensure that you appear on point, you must build on that foundation.
If you’re going to a sporting event in a solid tee rather than a team jersey, wear a team cap, especially if your hair isn’t looking so hot.
A watch is something that I have worn on every single date that I have gone on.
Consider this for a moment.
For the next few hours, your date will be scrutinizing every detail about you.
A wristwatch is a must-have!
It represents responsibility, maturity, punctuality, and demonstrates that you are a responsible adult.
Necklaces, sunglasses, and rings are all accessories that may elevate your look.
I’m a big fan of wearing accessories. I believe it enhances everything, but be careful not to overdo it and wear too many at once.
You certainly don’t want to resemble a Christmas tree.
Upscale Date
Then there’s the upscale date.
It could be a trendy bar or lounge, or a fancy restaurant. The majority of these are intended for use at night. These aren’t your typical daytime attire.
Please keep this in mind.
To be honest, I prefer this type of date since it allows you to show off your personal flair.
If you’re going on an outdoor casual date, you can dress up a little more.
A dark wash denim would be my go-to outfit for something like this. Solid black or dark grey would work fine most of the time.
If the weather permits, I wear boots with a sweatshirt and a leather jacket. If you’re going to be edgy, this is the way to go.
A tee shirt and jacket combination, on the other hand, works just as well.
The glasses will certainly offer a beautiful touch, indicating that you are also intelligent.
If you’re looking for something less edgy and more sophisticated, I recommend a white Oxford, which is incredibly clean and traditional.
Cropped trousers with a hint of the ankle. You look great in this attire, and your loafers will stick out as well.
If it’s cold where you live, don’t forget to bring a coat. Otherwise, it is unnecessary. It’s enough to wear a white Oxford shirt. It looks good.
Last but not least, I enjoy the look of wearing simply a shirt underneath, especially if the tee is of good quality or has some texture. It’s dressy, but it’s not necessary to wear a shirt or tie under the jacket.
Dinner at a Family’s Home
These latter two outfits are also appropriate for the type of date I’ll be addressing next. To be honest with you, the dinner date at a family member’s place is my least favorite type of date.
Don’t get me wrong: I think it’s great. These can be entertaining at times, but first dates are difficult enough. You also have the added strain of appearing in front of other family members you haven’t met yet, such as her mother or father, cousin or uncle. It’s quite a lot!
So, at the very least, know that you are dressed to impress to relieve some of the burden.
For this occasion, a white Oxford shirt is ideal. Navy slim-fit trousers with lovely brown leather shoes will also look great here.
Don’t forget to wear your watch to indicate that you’re an adult who is responsible and not a child.
First Date Outfit Ideas
You’ve got a sizzling date with that stunning senorita, so congrats.
You approached and you asked like a gentleman. Yes, she said.
You’ve secured a date. This isn’t just any date. It’s a first date, after all.
The onus is now on you. What I’d like to know is what you’re going to wear.
If you say I don’t care if I’m dressed too casually or sloppily! It’s over before it even begins.
4 First Date Outfit Ideas
Two outfits for the day and two for the night. They’ll transition from casual to semi-formal.
Let me paint a picture of a first date. You’re going to have a cup of coffee, possibly a latte, sit down, talk, listen to music, and do some people watching. It’s a daytime event with a laid-back vibe.
I’m trying for a classic bad boy look. I’m putting on my boots. You have the option of going chukka or Chelsea.
I’m wearing a pair of awesome lightly distressed denim pants. They have to be a good fit for you. They can’t be too beaten up, and the wash can’t be too black. We’ll reserve those for later in the evening.
You could wear a t-shirt as far as shirts go. I’m thinking of wearing a fitting v-neck.
But I’d make sure to throw on a beautiful leather jacket as well. It’s a bad boy look. Who can say no to this? You could always wear a three-button Henley instead of a t-shirt.
It’s fine if you don’t like this appearance. There’s also outfit number two, which is still casual but is a little more dressed up.
You’re wearing a pair of light casual chinos and perhaps a light v-neck sweater.
A good mid-range loafer for the shoes. Wear socks that are both matching and coordinating. The loafer is an excellent choice because it is casual, not too fancy, and you don’t have to worry about untying your shoelaces.
These are two excellent casual first date ideas.
Next, it’ll be nighttime; what will you wear? You still want to wear jeans, but you want to dress them up a little more.
The shoes are playful and fun, and they’re a step up from the casual shoes you wear during the day.
You’re wearing dark denim jeans, of course. For first date evening attire, a simple pair of dark wash denim is your best bet.
In terms of the shirt, I’m going with a classic white Oxford that fits well. Something about the pure simplicity of it appeals to me much. I believe it is the best solution. It’s not overly ostentatious or flamboyant. With this bad guy, you’ll never go wrong.
But let’s take it up a notch in terms of formality.
Maybe you’re going dancing on your first date, or maybe you’re heading somewhere lovely. You’d like to dress up a bit.
A great dark monochromatic appearance is always a good choice.
I wore charcoal gray pants and a lightweight v-neck sweater over a white collared shirt. You might wear a shirt of a different color. A simple black slip-on loafer completes the ensemble.
You’ve secured a date. It’s not just any date; it’s your first. If everything goes well, it’s aces. If it doesn’t go well, you’ll be having a lot more first dates.
Hopefully, this guide has given you some inspiration, sparked your creative style juices, and given you some ideas for what to wear the next time you ask that special senorita out and she said yes.
