The Crown You Wear
“Life is like a new Hat, You don’t know if it suits you if you keep trying it in front of the Mirror.”
Hello Gentlemen. I hope everyone’s week is going well. This week we are getting back to fashion. We covered shoes, now it’s time to cover your head. It’s getting warm (in halfway hospitable places to live anyway), the sun is coming out, and everybody’s starting to get their summer fits together. Hats are a great way to express yourself and add flair to that fit. Hats can be worn almost any time of the year but they can make even more sense with the sun being out there is a wider group of hats that can make sense to wear.
Quick Disclaimer: We will not be covering “casual” hats. Snapbacks, Fitteds, Trucker Hats, 5 Panels, etc are not being covered. This is a refined gentleman’s blog. While what you wear is not a general reflection of if you are a gentleman, no one sees a ball cap and thinks “That one refined guy right there, I tell you whut.” So for the purpose of this entry, they aren’t being covered.
Back in the day (like 60+ years ago) ball caps weren’t a thing. The only people wearing those types of hats were baseball players and military members. Because of the way clothes and hats were crafted back then if you wanted to keep the sun out of your face you were wearing a hat with a brim. A fond memory I have is of a picture of my grandfather (r.i.p) when he was young circa 1950. He had a farm and it was a picture of him with a plow and an ox pulling it. He had on a pair of slacks, a collared shirt, suspenders, and a fedora (more on that part later). These days that would be one stylish man, but in his day it was considered work clothes. There was a time when hats just went right along with the outfit. If you were wearing a suit back then and you were outside you had on a hat, simple as that. Depending on the era different types of hats were acceptable. Over time (like the 80s and through the 90s) hats with suits basically fell out of style and are just now making a come back. In the early 2000s (think 2005 or so) more “formal” hats started making a come back with more casual ensembles.
Fedoras were the standard if you outside in a a suit
One disclaimer before we get into the details of these hats. Hats do not belong in any situation that requires black tie or white tie attire. Unless it’s a theme party (think roaring 20s) hats don’t belong in any Gala-type situations. A good rule of thumb is if you’re wearing a tuxedo then you should not be wearing a hat under any circumstance that isn’t religious. Showing up looking like a smooth criminal extra at a Formal Ball or Gala is a major risk, one that may keep you from getting into the event or will get you eyeballs for the wrong reasons.
This should not be you at the Gala
We'll start with the most popular/stylish hat: The wide brim fedora. This is one you'll find guys rocking at brunch and in trendy fashion videos online. The Wide Brim like most of the hats on this list works both casually and with a suit.
Wide brim Fedoras also come in two major styles: Flat Brim and Pencil Brim. The styles are basically interchangeable and choosing one is more of a personal preference. I have versions of both in my collection.
Standard Wide Brim
Pencil Brim
The next stylish hat that I’ve seen making a comeback is the Pork Pie. Named so because of its visual similarity to the popular English meat pie. The pork pie was a staple in the 1930s and was a hat worn by many jazz musicians of the time but had fallen out of fashion by the 60s. In my opinion, it pairs best with more casual ensembles. It can make a suit more casual if that’s the look you’re going for. It’s also another look that is good for all seasons in those climates without harsh winters
A nice felt pork pie, just like mom used to make
The Trilby is another smaller brimmed hat. These hats were pretty popular during the style wasteland that was the first decade of the millennium. I’m not the biggest fan of the Trilby but it definitely has some great applications with some suiting options. I’ve seen some great ensembles that a good Trilby completed perfectly.
A standard Trilby. Short, Sweet, and Straight to the point
The next is the classic fedora. The iconic Mob hat was also popular with musicians and really any type of guy that was known for getting these done in the 1950s and 60s. This is the hat that wide brims call grandfather. A key difference is that like Trilbys these hats typically have an indented (or creased) crown. They are often a softer brimmed hat than their wide-brimmed descendants. I often see these hats in more tropical waterside cities such as Miami. They are another individual style hat that can work really well with casual ensembles. Before we get to the final hat type, we need to discuss something that applies to all the hats above and how they work.
Mob Ties
Accouterments.
Hats have become so much more varied than their original era counterpart. Crowns, Feathers, Stitching, Underbrim, Band Trim, there can be a lot going on. How do you know what works and what doesn’t? I think the best place to start is to identify your individual style. Do you have a higher energy brighter, style? More subdued? Quiet? It matters because the hat can make or break the ensemble. If you’re a high-energy style get a fedora that has a similar energy as your high-energy outfit. If you’re more subdued go with a fedora that matches the energy of the outfit. If you’re a more quiet style pic a fedora that is louder than the rest of the outfit, as it will add a little bit of pop to the whole ensemble.
The final hat style is the flat cap/Newsboy. These caps were the casual caps of yesteryear championed by both men and boys alike. Brands like Kangol made these the official uncle hat (especially when worn backward) but they have been making a comeback for younger men in the past 8-10 years. These hats a suited best for a casual outfit, but I have seen them worn by some with suits for a “peaky blinders”/”dandy” sort of look.
Don’t hurt nobody
Gentlemans hats are another form of self expression in your ensemble. They aren’t necessary the way shoes are, but if you know what you’re doing they can really pull an outfit together. If you don’t know what you’re doing then its likely to back fire and you may turn into a meme.
Have fun with your hat wear. Remember there are very few hard and fast rules. The rules that do exist are definetly hard and fast rules though. Be prepared to be barred from an establishment or an event if include a gentleman’s hat in the wrong way. There are other hats that weren’t covered but most of those hats aren’t very flexible. These hats are all the kind that will work in 90% of your wardrobe while also helping you to express yourself in a way that helps you stand you.