Hats Helped My Dating & Social Life as a Bald Man

Going bald sucks. That is undeniable for most men. But if you allow it to consume you, then you allow it to be an impediment to your success in life.

The important part about going bald, is that you learn how to deal with the psychological impact of it.

Some guys don’t bother to go that way at all. They chase restoration and fundamentally refuse to let go of their hair. More power to these guys. If you can reasonably find a way to save your hair line you should absolutely go for it. See recommendation in the notes about this.

But for those of us that are too far gone, unable to afford transplants, or just not responsive enough to chemical restoration, we have had to overcome the insecurity of male pattern baldness out of necessity.

I think the experience of going bald is not widely understood by those in society that haven’t been through it themselves. Especially for those like myself who started to have noticeable loss at the age of 21.

My head at 27 years young.

How going bald feels and affects you

Much of society has little to no sympathy for guys that go bald early. And when you lose it younger, your social circle can be a touch more insensitive about it than say if you went bald in your 30s. As it started getting noticeable jokes began flying in at my expense, and besides that just general comments in passing and people asking about to start conversations. Most people acting either oblivious to your sensitivity or revelling in it when making jokes.

Its easy to tell someone to have a thick skin about this stuff. When it came to the day to day handling of these occurrences I was fine obviously, often I would brush it off in a self-deprecating manner.

But when you are concerned something makes you less attractive, and that forms into an insecurity, for it then to become a running joke in social circles and defining characteristic in said groups …….

… well lets say it compounded everything into an obsessive depression. Which lasted for a few years.

This experience also ran simultaneously with my attempts to have success in dating. I can’t lie and say I was particularly successful in this area initially.

The hat advice I got from my mentor

In early 2019 I found a mentor in life who made me focus on self-improvement. He saw that I had a deep insecurity with my hair loss, and it was holding me back. His solution was simple.

Wear hats all the time like he did.

And that was it. He gave me permission to wear hats to cover this insecurity and get around it.

And now I pass that permission on to all of you.

Credit: @magic_fox nailing several hat styles here.

Wearing hats on every date

Every single date I’ve been on since then I have worn a hat. Mostly baseball caps. They become an integral part of my style. I was living in Australia at the time and caps are ubiquitous out there for practical reasons (its very hot and the sun is unrelenting). As such it was not difficult to get used to wearing baseball caps all the time, nor did seem a weird thing to do. Except utility was no longer my objective, now I was focusing on my style obsessively and the caps I wore had to be high quality and fit with the rest of my outfits.

Working them into my main online dating pics 

This sudden upgrade in style had a positive carry over effect with my online dating profiles. Now I was dressing better than I ever had in my life. Additionally, I had confirmed I looked better wearing a hat than I did otherwise. Using this newfound information, I significantly upgraded my online dating photos just through altering my fashion alone.

A key part of this process was also that I was much keener to take photos when wearing a cap. I went over this part of my insecurity in this article:

To recap, my hair loss made me reluctant to be in photos. Both with friends/family and just on my own. I hated the process of going to see how the picture came out and being instantly reminded of my rapidly shrinking hair line.

Remaining honest: I should note that I do include pictures of me with a shaved head on dating profiles. I think it would be dishonest not to do this. But for certain the best pictures I have involve me wearing a cap. As that is when I am dressed to my absolute best. The whole idea is about achieving your best presentation, not simply hiding an insecurity.

Wearing hats to every night out

Its more socially acceptable than ever to wear baseball caps almost everywhere. I can only recall one time being refused entry to club with one on a

But what happens when you have take the cap off?

Nothing happens. The girl you are dating doesn’t run off in shock amazingly. Neither do your mates that hang with you. I think this is for two main reasons:

  1. You have dealt with the insecurity which makes you act more confident and relaxed
  2. Your style choices allow you to make a much better first impression. Using style to improve how you look in one area tends to overflow into you improving all your style (at least I hope it does, don’t ignore the rest of your style)

To my fellow men everywhere, pay more attention to what you wear and how you present yourselves. If you take nothing else from this article go away with that.

Key Takeaways

The important part of this was learning that I could get on in life normally and well without having a good head of hair. Caps were a crutch I needed to come to terms with my hair loss

Its hard to get someone to love and accept themselves just by telling them to do it. They need to learn how to love themselves and work through their insecurities over time.

And I know there are bald/balding guys out there who are crippled by the insecurity. They could really do with a crutch while they build the confidence they need to overcome it.

If you are going to wear a baseball caps like I do it is important you have good quality options.

The Recommendation

This cap is the best I have found to date and should be your go to basic option. This was the first style of cap I ever bought after deciding to embrace them as a part of ‘my look’.

I am exceptionally picky and gave a few days of my life to trawling different retail outlets and sifting through their options. Most fashion retailers it turns out have meagre hat options. Almost everything is overbranded and tacky, and hats are usually thrown into a corner somewhere with the rest of the accessories.

I am going to save you time and cut straight to the best of the current market:

Flexfit 5 Panel Cap (affiliate link)

The beauty of this hat lies in the fact it has good structure but doesn’t greatly increase the size of your head. I prefer 5 panel hats to 6 panel hats from an aesthetic viewpoint, but also with regards to lowering the bulkiness. The design is mid-profile which is the best balance of shape and size.

Also this is a stretch fit hat. I will always look to recommend stretch fit hats if there is one available in that brand. I go into greater detail here as to why stretch fits are my favourite fit vs buckle and plastic snap closure: https://thehatfish.com/the-best-types-of-baseball-cap-closure/

The other key benefits are that it is single colour and the branding is hidden. Yupoong only brand their caps on the inside so you aren’t walking around as their loyal billboard. My recommendation is grab one of these caps in black for your primary go-to option. This grants you the most versatility and the lack of branding allows for more outfit combinations.

Thanks for reading guys,

The Hatfish


If you are interested in restoration as your primary response to hair loss, then I recommend you check out this youtuber:

More Plates More Dates is the best resource for scientifically backed information on preventing further hair loss and potentially regrowing lost hair. His focus is on bodybuilding and steroids, but the link above will take you to his playlist on hair loss prevention. The guy is legit. On top of knowledge I also think Derek has great insight into the mental impact of hair loss and talks honestly about a widely held, male insecurity from the heart.

Leave a Reply

Your email address will not be published. Required fields are marked *