I’ll be the first to admit that I’ve been putting this article off for a little while. The reason I have is quite simple too, it is just such a huge subject! Not only that but hats can be such an individualistic accessory that I feel wary trying to suggest ways for all you ‘beaners to wear them. But nonetheless, into its murky depth I tred…

I’m going to be talking first of all about hats that are more suitable for the casual occasions; the time when you are relaxing or slumming it with your friends, rather than when you’re heading to the office or on a night out. Although that isn’t to say that you couldn’t wear these hats with more formal attire, in fact it can often be a great way dressing down various pieces. But we’ll get into that later.

First of all, why wear a hat? There are plenty of guys out there who simply can’t stand them. They either don’t see the point in them or find that they just have one of those faces that can’t work a hat. Both of these are untrue and easily fixed. Hats provide a functional and practical purpose in the fact that during the colder months they provide you warmth and when the sun is out they provide shade and protection. When it comes to the belief that you just aren’t a ‘hat guy’ then all that means is you haven’t found the right hat yet. Hopefully this article and the one to come will help fix this.

Just before we start getting into the types of hats available to you, let me just make one mention of dressing seasonally because this applies to your headgear too. As with every piece of clothing you buy make sure that it fits the season you’re in. So for A/W I’m talking about knitted hats, whilst fabrics such as tweeds and felts are also a good idea too. When things start to warm up, then you can start moving into more canvas, cotton and straw oriented head wear.

Casual Hat Types

So here are the 3 main hats for casual dress:

  1. Knitted hat/beanie – I think the important thing to remember when wearing a beanie is to stay true to its shape. If the one you’ve got is folded up at the bottom then wear it that way (like Jack Nicholson in one flew over the cuckoo’s nest). If you roll it down then it’s going to be halfway between a tight and slouch beanie, which is never good. Similarly, if it’s a slouched version then let that bad boy slouch as much as it can! These types of hats are ideal for when you really are dressing down. Think jeans, t-shirts, plaid shirts, jumpers, anything that is as relaxed and warm as the beanie is. But remember when summer rolls around please don’t be one of those guys still wearing it. Get a straw hat instead, it will look better and wont get your head as sweaty.
  2. The Drivers Cap – heavily rooted in the English countryside, this has to be one of my favourite accessories at the moment. They always seem to look better and are far more durable when made from fabrics like heavy wools and tweeds. They can also transcend to the summer well if you buy some in lightweight cottons too. The great thing about the drivers cap is that they can really smarten up your outfit. Even if you’re only wearing jeans and a t-shirt, this hat will make you look more pulled together in an instant.
  3. The Big Old Trapper Hat – OK so this one is starting to make a serious come back and I’m really glad that I picked my own one up a few years ago in Moscow. The great thing about these hats is how warm they keep you! My head gets so warm that I don’t need to layer up as much for the rest of my body. However, the thing to remember with this hat is that you’re making enough of a statement by wearing one so keep the rest of your outfit nice and simple.
Ways To Wear

And as always here a few ways to wear the above headgear:

  • With a pair of stone coloured chinos, t-shirt and dark denim shirt wear a grey slouch beanie. Maybe trade the denim for a plaid version instead? If the rest of your outfit is in neutral colours then why not invest in a dark coloured beanie in reds, greens and blues? It’s a really easy way of injecting some life and colour into your looks.
  • Go all out English Gentleman at leisure and wear a grey tweed drivers cap with a white shirt, grey waistcoat and jeans combination. Maybe some form of vintage car is appropriate as well?
  • I find that a trapper hat tends to go well with understated pieces so why not wear yours with a standard Henley top? I’d recommend that you keep the hat in a neutral colour so that it gives you freedom to go crazy with patterns and colours with the Henley.

So there you have it guys a few ideas of what hats to buy and ways to wear them. Next week we move onto formal hats and ways in which to use hats to either dress up or dress down an outfit.