A Gentleman’s Style Guide to a First Date


Silas & Grace

You finally asked her out on a date and it was a success. Now it’s time to make sure that your first date is a success.

There are a few key aspects to focus on when preparing for this date, but one of the most important things to pay special attention to is what you wear.

It seems simple enough, but it can determine whether she accepts your offer for a second date or not.

It might almost seem shallow, but dressing like you care shows her respect and when respect is given, it can lay down a strong foundation for something that might just last.

Us men want to be prepared for the setting and for our date’s impression, but we also don’t want to overthink and over-stress. So this is a guide to help you simplify your decision and get a great result.



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 want to 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.

On the other hand, a V-neck t-shirt with a nice design or color, paired with a light jacket can make an easy to put together outfit.

The Bottoms: This part isn’t tricky at all. A pair of dark wash jeans can go with many tops and makes you look well put together, but still casual.

The Shoes: Throw on a pair of clean canvas shoes and you’re ready to go for this 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 classy or has a fun air about it, 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 started, 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.

The Bottoms: 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.



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 with putting some good 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.

The Bottoms: 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 translate into 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 small 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.



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. If you choose the button up, pair it with a bowtie with a great design. And if you’re feeling slightly eccentric, finish it off with suspenders.

The Bottoms: 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.




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.



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.



If you can, try to make sure the fabrics you wear are light and can breathe so sweat doesn’t become a factor.

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.

Now if you have any tips and advice on a how to dress for a first date, or there’s something you want answered, just let me know in the comments or email me! I’d be glad to hear what you have to say and perhaps write a response post!


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.

Fashion Style

Silas & Grace

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.

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