Dressing For A First Date In Your 40's (EASY Tips)

Are you a middle aged man who wants to make a really good impression with a new girl?

If so, this guide for dressing for a first date in your 40's will help you get on the right track.

In this post, you'll learn:

  • The do's and don'ts of men's dating style in your 40's
  • How to avoid common turn offs which will make you look like Grandpa Joe

And so much more. Keep reading to find out:

Dressing For A First Date In Your 40's

The great thing about middle aged men's style is that you don't need to run out and buy a whole bunch of expensive clothes to look good.

You just need to put things together in the right way, and avoid a few dating faux pauses. So first, let's cover a few middle aged dating mistakes guys make:

Critical Dating Mistakes Guys Make In Their 40's On A First Date

#1. Wearing Running Shoes

Unless you're going for a run with her, then leave your running shoes at home because they're really just meant for running. 

Running shoes do not go well with street clothes.

#2. Wearing Oversized Clothing

If you're wearing something that's big and baggy that looks like a garbage bag, then you may be on the wrong track.

And also, if you're wearing really big shirts to hide your stomach, then maybe you should deal with your stomach and wear some proper fitting shirts afterwards.

Oversized clothes look sloppy and they just fit badly.

#3. Messy Hair And Other Hygienic Issues

Have a good shave and actually style your hair before going on your date.

It will make a really big difference in the impression you're making on your first dates.

I've seen it before, guys coming out with me on bootcamps unprepared. They had much better reactions after having a proper shave and styling their hair properly as well. That includes getting a good haircut.

So that brings us to our next section:

Style Basics To Have A Great First Date In Your 40's

Here are some basic guidelines for dressing for a first date in your 40's:

#1. Wear Clean Street Shoes

Not only should you not wear running shoes, but wearing a good, clean pair of shoes is going to take you a long way and make a good impression.

#2. Wear Fitted Clothing

Wear something that actually fits and shows off your form. And above all, it should also feel comfortable.

#3. Be Casual But Sharp

Don't show up on a tuxedo if you're just going for a coffee or drink.

Unless you're actually going to some kind of formal occasion, then you're going to obviously dress up for that. But otherwise, keep it casual.

Wear your regular clothes. You don't have to run out and buy anything.

Just make sure you have your best pair of shoes on, some nice jeans, a fashionable jacket, and a wrinkle-free shirt. These are all you really need. And obviously, greet her with a smile.


Here are some common questions about dating in your 40's:

How Do I Look Hotter at 40?

To look hotter in your 40's, you should be really thinking about your health and getting in shape.

So get in the gym, eat good foods, and get good sleep. It is going to take you a long way to actually looking better in your 40's.

Are Jeans Okay on a First Date?

Jeans are okay on a first date because most first dates are going to be very casual. You're most likely going for a coffee or having a drink.

The only time you wouldn't wear jeans on a first date is if you're going for something more formal.

For more first date info, check out this  post.


Here is everything you need to know about dressing for a first date in your 40’s:

Critical dating mistakes guys make in their 40's on a first date: 

  1. Wearing running shoes: they don’t look with street clothes, and they will seem out of place on your outfit unless you’re going on a run with her
  2. Wearing oversized clothing: most of the time they look sloppy and don’t fit very well, so it’s best to avoid them 
  3. Messy hair and other hygienic issues: make sure you impress her by having a good shave and fixing up your hair, it makes a world of a difference

Style basics to have a great first date in your 40's

Remember, the basic guidelines are:

  1. Wear clean street shoes
  2. Wear fitted clothing
  3. Pick an outfit that’s casual but sharp

If you’ve got any questions or comments, leave them below.

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