When it comes to hats, it seems to be ‘do or do not, there is no try’. It is a trend that waxes and wanes, so your choice, either way, is likely to inspire some division. If in doubt, avoid the hat, but if you are a brave soul, or perhaps you simply need protection from the sun, read on.
Gentlemen’s choices in hats are fortunately more varied than perhaps we deserve, though certainly not as varied as women’s options. You’ve decided you want to, or need to, wear a hat, so the question for you now becomes, what sort of headgear would you like to make part of your personal style? This is an exceedingly difficult question, and one that men all too frequently get completely wrong – and often times, even when they get it right, people will still disagree.
Some choices in headgear are regional in nature; for example, if you are located in Texas or certain parts of the midwestern US wearing a “cowboy”, or ten-gallon, hat is an acceptable choice and can go with many types of fashion, even formal at times. However, outside of those regions, even if you are actively employed as a cowboy, unless you are actively roping cattle at that exact moment, wearing such a hat comes across as a major fashion failure.
One popular choice in headgear is the immortal fedora. This word conjures up different images for different people, ranging from the wide-brimmed variety worn by Indiana Jones to the more abbreviated-brim version many people are familiar with from shows such as Mad Men or The Blacklist. Many men choose the fedora because it is an outstanding-looking hat of its own accord, and has been worn by fashion icons throughout the past century. As well, the wider-brimmed version is often found as functional headwear for people working outdoors where they get high exposure to the sun, though less so as a fashion statement, and more for functionality.
Setting aside the wide-brimmed version, which is rarely chosen for fashion purposes, there is an unfortunate truth that I would like you to face regarding the common short-brimmed fedora. The odds are very good that, unless you look like Jon Hamm or James Spader, it is very likely that a fedora is more likely to make you look like an ungainly middle schooler trying to be cool at their formal dance, than you are to look dashing. Painful to realize, I know.
Now, is that to say that they do not work for anybody? Far from it! Obviously, there are some people for whom a short-brimmed fedora works very well, but please double, triple and quadruple-check with people you trust, and people that you don’t know (and that aren’t trying to sell you the hat), whether or not it suits your face and figure before going down this rather-expensive road. And fedoras, in particular, if buying of any quality, do start in the ‘quite pricey’ range, and go up from there.
Fortunately, there are other options available. Two that come to mind quickly are the ivy cap, sometimes called a flat cap, and the newsboy cap, which is somewhat similar. These have had a resurgence in popularity of late, and though they do not make the movies or TV shows quite so frequently, when you are aware of them, or make them a part of your own fashion, you will see them far more often (part of that Baader-Meinhoff phenomenon, the frequency bias we look for). They are fashionable, simple, and more understated than their tall, fully brimmed fedora counterparts.
Newsboy caps are slightly puffy and have seen a renaissance recently to their appearance in the show Peaky Blinders and are not to be overlooked. Ivy caps are similar in style but tend to be more streamlined, and have somewhat more variety and options, having regular and slim versions, flat-billed versions, stitched or unstitched bills – whether or not the material that overhangs the brim is attached by stitching or not – and indeed a uniquely American variant called the Boston Scally cap, with has a fuller roll of material over the brim, and a more deeply curved brim..
These Newsboy, Ivy, and Scally caps are made by a number of manufacturers in a variety of materials, the most versatile of which is virgin wool, or for summer wear, a linen or linen blend, or sometimes even silk or cashmere. These caps have an advantage in that, for travel, they can lie flat or nearly flat when packed into a bag. When worn not as part of more formal attire such as a suit, they can even be rolled and stuffed in a back pocket, which was common amongst newsboys and other gentlemen going back to the roaring twenties.
While there are modern variants of these, such as those popularized by the brand Kangol, as with many things, I find it is best to stick with a traditional variant, as Kangol caps tend to be something more akin to a sportswear brand than a day-to-day brand, much less for formal attire. As an addition note, as a gentleman, if you are not a professional baseball player, and/or currently at a baseball game or other sporting event at that particular moment, or otherwise engaged in very relaxed activities that would commonly involve t-shirts being worn, you should never find yourself wearing a baseball cap. Any time you are wearing any form of clothing that meets the standard of a shirt that has buttons or above, the bare minimum you should wear with regards to headwear would be something akin to an Ivy or newsboy cap.
While these are just some of the basics with regard to the choice of whether to wear a hat, and if so what variety, it is still a very personal choice, and one that you must ensure you tailor to fit well with your overall personal style while ensuring not to be too trendy or flashy. Wear hats at your discretion, but remember that unless you are Don Draper, there will always be those who question your choice. More to come!
