You finally asked her out on a date and it was a success.
Also, you figured out the perfect location and you know the conversation topics you wanna talk about.
Now it’s time to make sure that you know what to wear on a first date. Should you go with your personal style or try out some new date night outfit ideas?
And while this sounds pretty simple, it can determine whether she accepts your offer for a second date or not.
It might almost seem shallow, but when you dress to impress, you’re showing that you care and respect her. And when respect is given, it can lay down a strong foundation for something that might just last.
And if you wanna be prepared for the setting and for your dinner date, then I hope these simple first date night outfit tips help you. Don’t overthink it, just apply some of these ideas from this first date guide for gentlemen’s style and let me know how it goes!
What to Wear for a Coffee Date
If you’re not sure what to wear on a coffee date as man, then I’ll help break it down for you.
The coffee date is great, it’s low key and low commitment. Because if you don’t end up being interested or she turns you down for a second date, you didn’t invest much money into what didn’t last.
That said, you still wanna take careful note on what you wear. You can remain casual, but let her know you’re interested by showing that you care how you look for her.
The Top: A simple go to for this kind of date can be a button up, whether short or long sleeved, with a color that pops. This is optional, but it’s a great way to make the rest of your outfit stand out without trying too hard.
And if you go with a button up, linen will always make you look great. 👍
On the other hand, a V-neck t-shirt with a nice design or color, paired with a light jacket can make for an easy to put together outfit.
Pants: This part isn’t tricky at all. A pair of dark wash jeans can go with so many tops and makes you look put together, but still casual.
The Shoes: Throw on a pair of clean canvas shoes and you’re ready to go for this date!
THE FINE DINING RESTAURANT
This is probably where you might be more than a bit concerned when it comes to men’s fashion for first dates. But I’ll help you!
If you’re taking a girl out for a fine dining experience, then she’s probably pretty special to you. And this is where you really want to compliment the restaurant choice by putting some thought into your look.
You picked a great place, so show her you have great taste in more than just restaurants.
The Top: Here’s where that versatile button-up top comes in again. But don’t leave it as is. Pair with a bowtie or a tie. Be careful with the ties though, you don’t want to come across as if you just got off of work. Find a fun pattern that isn’t too loud, but gives off a bit of your personality.
Next, layer it over with a blazer or sports jacket to finish it off. You can either stay safe with a navy blue or you can go for color, just make sure it pairs well with your clean and unwrinkled shirt.
Pants: Here you can either pair your top with khakis, matching or complimenting dress pants, or even black jeans. Sounds strange to pair it with jeans, but black jeans are also very versatile and can work in many situations.
The Shoes: Go for some clean top-sliders or dress shoes and find socks that stand out. She’ll see that you have taste and can have fun with your look (in a quietly eccentric way).
*Last note on this: If you’re thinking of wearing a suit, then by all means do it. The only thing that changes is the pants and jacket itself. Just make sure to wear something that compliments the chosen color.
FOR THE CRAFT BREWERY DATE
A quick note about this kind of date; context is king. If you’re taking her to a place that has a lively creative atmosphere, you still need to make sure you know what kind of people may go there.
Sometimes, even if a place is fun or classy, dressing up too much may make you feel awkward. It’s still a place where people can go after a day of hard work to unwind and be a mess as well as a place for those wanting a quick drink and dressing very casual (maybe too casual).
Know the crowd and dress accordingly.
Now with this said, craft breweries are still a great place to take a date if the establishment has a great atmosphere or charm. And when you pick your outfit, you want it to flow with whatever crowd happens to be there that night. Not to say, dress like a slob, but don’t overdress.
The Top: A light or thicker long sleeved henley with a dark or neutral color will give you a smart look. It isn’t over stated, but it’s definitely not dressing down.
You can also opt for a button up as mentioned before, but choosing a color that pops isn’t necessary. Just make sure it’s clean and crisp and you’ll look great.
Pants: Dark wash or even black jeans are appropriate for this occasion. Again, they go with whatever top and shoes you’re wearing and aren’t too formal like khakis.
The Shoes: A pair of top-sliders or the right canvas shoes are an easy addition to the look.
*Last note on this: If you aren’t afraid to dress a little more formal and stand out, then go for it. Wear that bow tie, put on those dress pants, and pick a great color.
FOR THE INTERNATIONAL DINING EXPERIENCE
Here is where you take her to that amazing Thai restaurant in downtown, or your favorite place to get Mexican. Obviously, you’ll want to make sure that it’s a place to impress, not a hole-in-the-wall restaurant that has no class at all (unless you’ve found out that the both of you are into finding small unknown restaurants with great food).
The Top: With this one, since there aren’t any specific rules, you’ll get to have some fun. Go with a cool pattern or color for your button up or V-neck. And if you choose the button up, you might wanna pair it with a bowtie with a great design.
Pants: Of course, depending on whether you choose the V-neck or a button up, dark jeans or khakis can be a great pairing. Even though this is a sit-down restaurant, there’s no need to wear dress pants unless the outfit really calls for it.
The Shoes: Canvas shoes and top-sliders along with some colorful socks (or with a cool pattern) is a great way to finish off the look.
Whether you dress it up or dress it down, just make sure things are paired well and visually pleasing for your date.
QUICK FINAL TIPS
1. Give Her Context
Make sure that in every occasion (especially on a surprise date), you let her know how she should dress. Then she’ll be prepared if the setting is formal, informal, or somewhere in-between.
2. Accessories
The small details like socks is what makes your look finished. But you can also compliment any outfit with a nice watch or a pocket square.
3. Hygiene
If you can, try to make sure the fabrics you wear are light and can breathe so sweat doesn’t become a factor.
Also, it goes without saying to take care of your oral hygiene and to put on deodorant, but just make sure that when it comes to cologne, you don’t douse yourself. You don’t want your scent to be a heavy cloud around the both of you as you’re eating.
In the end, just remember that this person you’re taking out on a date may be the right person.
You want to create a great memory to remember and share with others into the future. So dress for the occasion and act as though you met the one, because you just might have.
PS – What were some of your favorite tips for men’s first date fashion?
Chasing Foxes was started in 2016 as a way for Grace and her husband, Silas, to start traveling. However, they started to realize that they had a passion for improving themselves, and wanted to help others level up their lives as well. So whether it's with cooking, travel, or staying healthy, they want to help you better your life bit by bit, as they do the same.