Dress Hats

I have a grey lite felt fedora by Bailey, I wear it when it's snowing out. I also like the paper-boy cap, to me that feels more casual.

I wear a fedora with my suit quite a bit. Not much to it, just do it.

Beaniecopter hats are a personal favorite of mine. Its color is cherry and grey with an apollo patch on the front.

Yeah, just get use to it.

You'll get a very mixed reaction on this one - it has been discussed quite a bit on SF.

On the one hand there are those here who love hats and wear them regularly, and on the other there are those who think them antiquated costume not fit for wearing by the modern gent.

Regardless of whether or not you believe hats to be anachronistic, the often cited aversion to hats on the grounds 'I can't pull them off' doesn't hold a lot of water.

Hats are hugely diverse and just as suits of different cuts flatter men of different proportions, so too hats of varying dimensions, in terms of brim, crown and so on, work differently for different heads and faces.

The problem with this is it takes a lot of searching to find the right hat for your face, even though it's certainly out there. This is made all the more difficult by the lack of hats in the mainstream and the decline of millinery as an art and trade - it was tricky enough to find the right hat before, now with the decline of hats there's a huge amount of effort and/or luck involved.

Then there's dealing with the social stigma of wearing one. This isn't such an issue if you opt for a trendy trilby and wear it with a shirt and jeans, but try incorporating a more traditionally styled hat into smarter attire and you're going to get the retro label, like it or not. Some can apparently be thick-skinned about this and shrug it off, while others wish for the days when it was normal so they could still get away with it without feeling like everyone views them as a throwback.

I've been wearing a fedora pretty much on a daily basis for about a year now. I'm 35 and I mainly wear them with suits and overcoats. So far, I've only received compliments. Another good colour to get is a dark grey - goes with lots of things including black overcoats.

Fedoras are great to keep snow, rain, and sun off your head and face! Experiment with different brim widths to find a size you are comfortable with.

That's because no one's going to tell you to your face it looks bad.

Sorry I'm in the anti-hat group, though even more anti-fedora... you'll either look like a hipster or a sleezy lawyer/accountant who thinks it makes him look more 'honest' or 'cool' or whatever; and if you're in politics I'll just think of herman cain. Now a fedora with anything but a suit could look decent, i concede.

I'd have more tolerance for something like a bowler, a hat almost exclusively seen with suits.

Oddly enough, I've never been a big fan of bowlers.

The only other thing I'll say regarding the whole wearing of hats thing is that if you enjoy wearing one, why worry if others don't like it? I certainly don't.

This.

Wear it with attitude, the attitude is right it will look natural.

I wear some sort of fedora most of the time when I am out walking my dog if the weather is too cool for one of my Panamas. I like fedoras with casual and dressy casual attire. With a suit, unless dictated by weather, it does strike me, after due consideration, as being a tad retro-costumey.

If you're comfortable wearing them and people compliment you with it then by all means continue wearing it.

 

really depends on your preference, it's an accessory not a necessity in your attire

TKE, not to be a dick, but I think this is a terrible idea, if not for you personally. I'd really have to see it on you. In your pictures you seem to have quite a small head/neck and rather broad shoulders. I think a hat might more call attention to these off-set proportions...