# Dressy, non-pretentious headwear for men
**URL:** https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103
**Category:** In My Humble Opinion
**Created:** [April 20, 2011, 5:27pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103 "2011-04-20T17:27:18Z")
**Posts on this page:** 20
**Page:** 1
### Author:  [@MichaelEmouse](https://boards.straightdope.com/u/MichaelEmouse)
#### Post date: [April 20, 2011, 5:27pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/1 "2011-04-20T17:27:18Z")
I have a problem many other men also have. I work in a cold climate and wear a suit to work.
I shave my head so it gets rather cold. I’ve noticed that tuques (knitted hats) are effective at keeping me warm but they really don’t match the dressiness of a suit.
Fur hats with flaps on the side are even more effective than tuques at keeping warm but they’re even more liable to look silly when worn with a suit.
I’ve thought about buying a hat like most men wore before the 60s but I thought that might look pretentious.
Are 50s hats prententious-looking when worn with a suit?
Is there any headwear I can wear with a suit that will keep my head warm while also fitting with a suit?
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### Author:  [@notquitekarpov](https://boards.straightdope.com/u/notquitekarpov)
#### Post date: [April 20, 2011, 5:47pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/2 "2011-04-20T17:47:00Z")
I guess it depends where you live.
In London I used to wear something in between a trilby and a fedora with a suit and overcoat and never got any hassel from anyone. I think anything that covers your ears is going to look pretty strange with a suit.
YMMV
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### Author:  [@RealityChuck](https://boards.straightdope.com/u/RealityChuck)
#### Post date: [April 20, 2011, 5:53pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/3 "2011-04-20T17:53:47Z")
[Ascot caps](http://www.hatsinthebelfry.com/category/mens-ascot-caps.html)
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### Author:  [@silenus](https://boards.straightdope.com/u/silenus)
#### Post date: [April 20, 2011, 5:59pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/4 "2011-04-20T17:59:26Z")
[Ushanka](http://en.wikipedia.org/wiki/File:Jay_z_2.jpg)
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### Author:  [@Jimmy\_Chitwood](https://boards.straightdope.com/u/Jimmy_Chitwood)
#### Post date: [April 20, 2011, 6:08pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/5 "2011-04-20T18:08:41Z")
Sure, you can wear a real hat. I do. People might remark on it, but I’ve never gotten the impression anybody thought I was acting like a dick because I was wearing a hat in the cold. I think the one I usually wear qualifies as a Homburg. It looks much better than a knit one would look anyway.
Also, if all you want to do is stay warm, don’t underestimate the power of a scarf.
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### Author:  [@Max\_Torque](https://boards.straightdope.com/u/Max_Torque)
#### Post date: [April 20, 2011, 6:11pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/6 "2011-04-20T18:11:35Z")
[Bailey Pieter Earlap](http://www.villagehatshop.com/bailey_pieter_earlap.html).
Less urban is the [Wild Boar Trapper Hat](http://www.villagehatshop.com/goorin-bros-wild-boar-trooper-hat-olive-green.html).
If it’s the knitted-ness of the toques that seems too casual, you could try a bomber hat, in [denim](http://www.villagehatshop.com/fudd_bomber.html) or [leather](http://www.villagehatshop.com/mad_bomber_leather.html).
Or, go full-on [cossack](http://www.villagehatshop.com/jaxon-cossack.html).
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### Author:  [@SeldomSeen](https://boards.straightdope.com/u/SeldomSeen)
#### Post date: [April 20, 2011, 6:15pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/7 "2011-04-20T18:15:44Z")
[Driving caps](http://www.duluthtrading.com/store/clothes-workwear/mens/hats-and-caps-for-men/mens-driving-caps/mens-driving-caps.aspx) look OK with a suit, if you get a good-quality wool or leather one. Fairly classy, but less pertentious than a hat.
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### Author:  [@MichaelEmouse](https://boards.straightdope.com/u/MichaelEmouse)
#### Post date: [April 20, 2011, 6:30pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/8 "2011-04-20T18:30:45Z")
Perhaps I should mention that I’m working as an articling student (i.e.: lawyer apprentice) in a law firm. I wear black or navy suits with white or pale blue shirts. The least conservative ties I have is a navy/purple Paisley.
I aim to have my whole work wardrobe be classy and understated. I want it to be the archetype of what you expect a lawyer to wear.
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### Author:  [@Jimmy\_Chitwood](https://boards.straightdope.com/u/Jimmy_Chitwood)
#### Post date: [April 20, 2011, 6:54pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/9 "2011-04-20T18:54:42Z")
I don’t know about _archetype_, but I am a practicing attorney. Dark suit, dark overcoat, dark hat works for me.
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### Author:  [@Max\_Torque](https://boards.straightdope.com/u/Max_Torque)
#### Post date: [April 20, 2011, 7:13pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/10 "2011-04-20T19:13:45Z")
Did you look at the first hat I linked? Reviews say things like “classy”, “looks great with a suit and tie”, and “a perfect winter hat.” I’d wear one if they came in my size.
Your OP made it sound like you didn’t want anything too “stuffy”, but frankly, that’s what the rest of your wardrobe sounds like. There’s not much difference between “stuffy” and “pretentious”, so if I were you, I’d roll with it.
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### Author:  [@MichaelEmouse](https://boards.straightdope.com/u/MichaelEmouse)
#### Post date: [April 20, 2011, 7:20pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/11 "2011-04-20T19:20:15Z")
> [@Max\_Torque](#):
>
> Did you look at the first hat I linked? Reviews say things like “classy”, “looks great with a suit and tie”, and “a perfect winter hat.” I’d wear one if they came in my size.
>
> Your OP made it sound like you didn’t want anything too “stuffy”, but frankly, that’s what the rest of your wardrobe sounds like. There’s not much difference between “stuffy” and “pretentious”, so if I were you, I’d roll with it.
What I want to avoid is an unusual, flashy, look-at-me vibe which would be incongruous with the rest of my wardrobe. I thought wearing an old style hat might give that impression.
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### Author:  [@Mollie\_Magill](https://boards.straightdope.com/u/Mollie_Magill)
#### Post date: [April 20, 2011, 7:29pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/12 "2011-04-20T19:29:49Z")
I wear a Stetson. Stetsons are cool.
It’s a Brown Felt one with a 3-4 inch brim, so while you could technically classify it as a “Cowboy Hat”, I don’t look like I should be wearing boots and belt buckle the size of a dinner plate. It also goes well with my non-black or grey suits.
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### Author:  [@Gary\_T](https://boards.straightdope.com/u/Gary_T)
#### Post date: [April 20, 2011, 7:47pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/13 "2011-04-20T19:47:44Z")
> [@MichaelEmouse](#):
>
> I’ve thought about buying a hat like most men wore before the 60s but I thought that might look pretentious.
>
> Are 50s hats prententious-looking when worn with a suit?
What is a 60’s hat compared to a 50’s hat? I would have thought they’re the same thing, traditional men’s dress hats. I don’t see how they’re pretentious.
> [@](#):
>
> Is there any headwear I can wear with a suit that will keep my head warm while also fitting with a suit?
Yeah, traditional men’s dress hats.
> [@MichaelEmouse](#):
>
> What I want to avoid is an unusual, flashy, look-at-me vibe which would be incongruous with the rest of my wardrobe. I thought wearing an old style hat might give that impression.
Wow. Seems to traditional men’s dress hats are the LEAST unusual, flashy, look-at-me styles. Now, I acknowledge they’re less common than they were decades ago (though they seem to be coming back), but they _GO WITH_ traditional suits and dress coats. Anything else runs the risk of grabbing attention for a clash of style.
> [@Mollie\_Magill](#):
>
> I wear a Stetson. Stetsons are cool.
While Stetson is perhaps best known for its western-style hats, it’s a long-standing company that makes quite a variety of styles, including [these traditional men’s dress hats](http://www.stetsonhat.com/collections.php?cat_id=5).
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### Author:  [@hogarth](https://boards.straightdope.com/u/hogarth)
#### Post date: [April 20, 2011, 7:48pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/14 "2011-04-20T19:48:20Z")
> [@MichaelEmouse](#):
>
> What I want to avoid is an unusual, flashy, look-at-me vibe which would be incongruous with the rest of my wardrobe. I thought wearing an old style hat might give that impression.
My two (Canadian) cents:
If I saw someone wearing the hat linked above (“Bailey Pieter Earlap”) with the **earflaps down** on a **cold day** , I’d think nothing of it. In that context, it’s clearly just a dressier version of a toque.
But if I saw someone wearing it with the **earflaps up** on a **warm day** , I might consider that person to be a bit of a dandy.
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### Author:  [@Palooka](https://boards.straightdope.com/u/Palooka)
#### Post date: [April 20, 2011, 8:02pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/15 "2011-04-20T20:02:44Z")
You can’t wear a hat with a suit but without an overcoat. That’s just how it is now.
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### Author:  [@Maastricht](https://boards.straightdope.com/u/Maastricht)
#### Post date: [April 20, 2011, 8:39pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/16 "2011-04-20T20:39:36Z")
> [@Palooka](#):
>
> You can’t wear a hat with a suit but without an overcoat. That’s just how it is now.
[This is correct.](http://answers.yahoo.com/question/index?qid=20070810182440AAIJgJe) **MichaelEmouse** , did you mean a cap or hat to wear with an overcoat worn over a suit? If so, I second the idea of a cap. Stetson has some [formal ones](http://www.hoedshop.nl/Harwinton-Pet-met-Klep-by-Stetson.html), even in [leather](http://www.hoedshop.nl/Cusetta-Leren-Ballonmuts-by-Stetson.html).
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### Author:  [@typoink](https://boards.straightdope.com/u/typoink)
#### Post date: [April 20, 2011, 8:47pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/17 "2011-04-20T20:47:41Z")
> [@Gary\_T](#):
>
> Wow. Seems to traditional men’s dress hats are the LEAST unusual, flashy, look-at-me styles.
I agree, but I understand where the OP is concerned: dress hats are coming back, but they’re mainly coming back with hipsters / urban youths. Fedoras and straw hats are pretty much part of the coffeeshop Mac guy uniform.
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### Author:  [@Maastricht](https://boards.straightdope.com/u/Maastricht)
#### Post date: [April 20, 2011, 8:53pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/18 "2011-04-20T20:53:52Z")
Related thread. [Is it rude to wear a dressy cap indoors?](http://www.quora.com/Is-it-improper-to-wear-a-Newsboy-styled-hat-indoors-in-the-workplace-or-at-business-functions)
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### Author:  [@MichaelEmouse](https://boards.straightdope.com/u/MichaelEmouse)
#### Post date: [April 20, 2011, 8:55pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/19 "2011-04-20T20:55:38Z")
> [@Maastricht](#):
>
> [This is correct.](http://answers.yahoo.com/question/index?qid=20070810182440AAIJgJe) **MichaelEmouse** , did you mean a cap or hat to wear with an overcoat worn over a suit? If so, I second the idea of a cap. Stetson has some [formal ones](http://www.hoedshop.nl/Harwinton-Pet-met-Klep-by-Stetson.html), even in [leather](http://www.hoedshop.nl/Cusetta-Leren-Ballonmuts-by-Stetson.html).
I’m mainly talking about a hat I’d wear outdoors with a suit, without an overcoat. I can deal with some cold when wearingt a shirt and jacket. Going outside when it’s chilly without a hat or hair is unpleasantly cold.
I see how it might be surprising to think of 50s hats as flashy and look-at-me, but since they’re so uncommon today, especially on twenty somethings like me, they might be seen as such. Also, as has been mentionned, the fact that hipsters wear them can make them quite likely to be seen as look-at-me-I’m-fashion-forward signs of flashyness which is not what I want at all.
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### Author:  [@Sunspace](https://boards.straightdope.com/u/Sunspace)
#### Post date: [April 20, 2011, 8:59pm UTC](https://boards.straightdope.com/t/dressy-non-pretentious-headwear-for-men/579103/20 "2011-04-20T20:59:34Z")
> [@typoink](#):
>
> Fedoras and straw hats are pretty much part of the coffeeshop Mac guy uniform.
:: blink ::
I am clearly going to have to take my Mac to a coffeeshop and write something, to see whether hipsters with hats appear. I don’t remember them at all, but it’s been a couple of years.
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