IANTFG (I Am Not That Fedora Guy)
September 30, 2010 1:56 AM   Subscribe

Can a late-20's white guy wear a suit with a hat without looking like a jerk?

The answer's simply "no", right?

I really like hats. I used to wear a flat cap with a suit, but there's no way that plays after age 23 or so. I've seen gray fedoras worn with gray flannel suits, but only by men over the age of 50. I've seen pork pie hats and their like worn with three piece suits with suspenders, but only by black men.

Am I out of luck? If I'm wearing a suit, what's the sharpest or snazziest or showiest hat I can possibly hope to pull off and still be taken seriously? In a social context? Surely not in a professional context?

Assume I have no fashion instinct whatsoever. In case it matters, I'm wide, usually chubby, and tall.

Snark about responsible hedonists will be cheerfully resented.
posted by foursentences to Clothing, Beauty, & Fashion (56 answers total) 5 users marked this as a favorite
As far as I'm concerned, you can wear whatever you want whenever you want. However, if I see someone wearing a fedora it is immediately obvious that they are trying far too hard.
posted by knowles at 2:13 AM on September 30, 2010 [8 favorites]

And why can't you keep wearing the flat cap? Make it match the suit, and it becomes part of the ensemble. You make the clothes, the clothes do not make you. It's all in how you pull it off. (Same goes with any kind of hat, really, but I advise against the fedora for many and really long drama filled reasons.)

If you have a friend or relative who knits, you could go that route -- there are about ten zillion hat patterns out there and some get downright amazing.
posted by Heretical at 2:24 AM on September 30, 2010

The key to looking good in a hat is not be self-consciously wearing a hat. It's a part of your personality of-the-day. Just like you don't button and unbutton your coat as you walk or a woman does not take out and put in her earrings as she moves through the day, so must you consider it a part of your movable feast. Don't worry what zealous blogs think of what happens on the street. The reality is most people don't care except when it's done really well or really badly. What you feel like wearing is up to yourself alone.
posted by parmanparman at 2:34 AM on September 30, 2010 [7 favorites]

also, you are completely wrong about flat caps.
posted by parmanparman at 2:35 AM on September 30, 2010 [4 favorites]

A lot of people will resent the fact that you have the testicles to wear a fedora at the risk of looking like a jerk!

I don't think there is a lot of "hat envy" out there, or people giving it much consideration beyond thinking that you are looking like you are trying too hard.

Bottom line is that if you are wearing a fedora (or other hat) to impress other people, you are aiming for a very small minority in my experience. Hats within a professional context are commonly used to cover perceived weaknesses in hairlines or to look "vintage".

Hats on men in a casual setting can be pulled off by the right overall look of the person, style, context, and attitude. Hats with a business suit is a tough look to get right.

So, if you wear hats because you like them and don't care what anyone else thinks, then go for it regardless. If you are trying to be perceived as anything other than somewhat pretentious by other people, tread carefully. I have never seen a young man wear a hat in a serious way successfully, unless they were being ironic or stylish to the point of costume (a la Johnny Depp).

So my vote is that if you have the look and attitude to pull it off in a casual context, you will be a trend setter and it'll all be good. If can't pull it off and wear one in a formal professional context, you'll look like a prig.
posted by qwip at 2:43 AM on September 30, 2010 [2 favorites]

My SO is well-built, tall, and late 20s, and he wears his beloved flat cap with everything. I'm serious, I swear he loves that thing more than me. And he looks great! In fact, it's very much his look now, he looks "more like him" with it than without.

We went out the other night and he wore a trilby with a suit. That looked ace as well.

The trick is confidence - if you think you look a bit naff or try-hard, it'll show to other people and influence what they think. Own the hat-wearing - decorate your noggin with pride!
posted by greenish at 3:51 AM on September 30, 2010

Always remember that a hat is intended to keep the weather off your head and should be removed while inside.

Also, these kinds of hats are more often found on the sysadmin set than the Bogarts.
posted by splatta at 3:57 AM on September 30, 2010 [8 favorites]

A good friend of mine is in his mid-thirties and has worn his flat cap for years and years - as long as i've known him. I've never thought he looked like a jerk. I actually think he looks great.
posted by ukdanae at 4:04 AM on September 30, 2010

My PERSONAL OPINION is that hats with suits are anachronistic and, thus, pretty try-hard. I will judge a man wearing a hat as a jerk nine times out of ten.
posted by Ted Maul at 4:15 AM on September 30, 2010

Personally, I love this look, and I wouldn't think you were trying too hard. As others have said though, it's all about being confident.

Heck, I had a friend who consistently wore bowties on nights out. It was his style statement. He looked great.
posted by so much modern time at 4:16 AM on September 30, 2010

You're right, flat hats look stupid. Suit and hat is only acceptable in the following circumstances:
- London banker look with dark grey flannel suit and bowler
- tails and top hat
- safari suit and matching pith helmet

Anything else is taking a risk you might not want to take.
posted by A Thousand Baited Hooks at 4:21 AM on September 30, 2010

Hats are coming back in for men. The trilby is back for young men in a big way, and a fedora isn't that different. If you feel comfortable and confident in a fedora, go right ahead and wear one.
posted by orange swan at 4:23 AM on September 30, 2010

Best answer: Fedoras are fine, but avoid slouching towards Trilby territory (shorter brim, turned up in back) because they've been ruined, temporarily I hope, by people like Justin Timberlake and Jude Law and this douche Kevin Federline who treat them as casual hipster accessories and wear them about a size too small. If you also invest in a good charcoal grey or black overcoat and then make sure that your hat's pattern includes that note (or echoes it in the band) you'll look put together. Avoid the all black fedora with black band and black coat; it's a hard look to pull off unless you're Hasidic.
posted by carmicha at 4:35 AM on September 30, 2010

Best answer: You've got some evidence right here: several people have said they would automatically prejudge you as a loser who's trying too hard, and others have said they think hats are cool and look nice. These are the real conditions to be found in the world. Some people out there ARE trying too hard, and others are rocking the lids because they like them and wear them well. So wearing the hat bears with it both risks and rewards.

I'm a firm believer that some conformity is a good thing: stopping at red lights, observing basic social niceties. I think you'd be foolish if you worry too much about the risk of being perceived badly by folks who are going to make a blanket statement about you based on whether you placed a hat on your head this morning. As others have said, if you like it and you think it looks good on you, put it on and don't give it another thought.
posted by itstheclamsname at 4:49 AM on September 30, 2010 [2 favorites]

Avoid fedoras at all costs. As Onstad established six years ago, you don't look like bogart. You look like you ride a Honda Goldwing and collect swords. I'd stick with the flatcap, if only because a significant number of people still wear them.
posted by The White Hat at 5:21 AM on September 30, 2010 [1 favorite]

It all depends on how you wear it. Another example in TV is the character Neal Caffrey from White Collar. He is supposed to be all sophisticated and fit in with the highest fashion rich people, but I think he looks dumb in the hat. And I don't think his suits fit right.

Johnny Depp can pull it off.
posted by CathyG at 5:27 AM on September 30, 2010 [2 favorites]

Best answer: Yeah, I think Neal Caffrey is a good example of Hat Gone Wrong. Clearly, it is part of his general look, but he fiddles and twirls it way too much to really make it blend in. If a hat is just a hat that goes with the rest of your outfit or has some practical use, then it's fine. If it's all LOOKIT MAH HAT, then it's gone wrong.

So you can wear your hat and be fine. Just don't make it all about the hat.

Also I see plenty of post-23 flatcaps, so you may still have a few years left in it.
posted by robocop is bleeding at 5:42 AM on September 30, 2010

Good work losing the flat cap. Resist the fedora.

No hat.
posted by Joseph Gurl at 5:45 AM on September 30, 2010

Best answer: So much hat hate. Is it cold? Is it too sunny? Then wear a hat.

Although looking at some of these pictures, I admit some of these hats look stupid. Men in my city who wear hats mostly do so to keep the weather off, and professional men mostly wear old-fashioned fur-felt fedoras. But, you know, to keep the weather off. Not at a rakish angle or anything.
posted by Eyebrows McGee at 5:57 AM on September 30, 2010

Best answer: Oh I wish wish wish wish that men could seriously wear hats. And touch them lightly when I stepped into the elevator. I'd be the first to insist that you wear a hat... except I just don't think that you really can. It'd be like if I wanted to seriously wear little white gloves on the street. Although I might be dead-serious, most people wouldn't think so.

Anyway, I agree with someone above who asked what kind of coat you're wearing, and I think this might lead you into possibly being able to wear a hat for-serious. Get a real man's grown-up coat, the longer the better. Wearing a hat without even a suit jacket will look like you're going for some look or part of some subculture that you probably aren't. I think basically wearing a hat needs to be part of a larger effort to dress like a grown man -- you can't just tack a hat onto to your untucked shirt, too-skinny unlined trousers, and clunky college-grad shoes and feel like you're pulling your look together.
posted by thebazilist at 6:08 AM on September 30, 2010

If you're wearing the suit out on the town, and the rest of your getup is super-hip...maybe.

If you're wearing the suit in any suit-requiring business context, no, sorry. Career-limiting move.
posted by a young man in spats at 6:08 AM on September 30, 2010

I don't agree- if you wear it though, you gotta OWN IT! You gotta work it like it would be INSANE NOT to have one on.
posted by TheBones at 6:18 AM on September 30, 2010 [1 favorite]

Trilbies are everywhere now, so you'll be fine with a hat. Although if you want to make a style-statement, avoid the trilby itself. It's the equivalent of a baseball cap now.

Always remember that a hat is intended to keep the weather off your head and should be removed while inside.

Heed this. There are really few things more gauche than a dude wearing a hat indoors. It's like having your shirt tucked into your underpants. Even in the all-men-wore-hats days, the first thing you did walking inside was take the damn thing off.
posted by griphus at 6:24 AM on September 30, 2010 [3 favorites]

I would stick with a flat cap. I'm from Boston, and that, even in the 80's, was the norm for people of all ages.

In my opinion, the only people that can "get away" with hats & suits are African Americans and Cowboys (in a different way).

But, if that's what you want to wear - then wear it.
posted by KogeLiz at 6:37 AM on September 30, 2010

Also, when I see white guys in fedoras and suits, I always think of Ducky from Pretty in Pink.
posted by KogeLiz at 6:46 AM on September 30, 2010

People care too much what other people wear. Be assertive, wear the damn hat.
posted by edgeways at 6:51 AM on September 30, 2010 [2 favorites]

Wearing a hat has to be a calculated part of a whole ensemble - you can't just stick a hat on and call it done.
posted by zamboni at 6:56 AM on September 30, 2010

I say wear the hat.

Also, I strongly object to the phrase "trying too hard" when it comes to fashion. If someone on the street accuses you of trying too hard, I'd counter by calling them lazy.

(I probably would not do this. But I would think it!)

Full disclosure: I wear hats.
posted by mmmbacon at 7:07 AM on September 30, 2010 [1 favorite]

I think a great inspiration is the wardrobe in the USA show White Collar. I think the Neal Caffrey character is, for the most part, dressed well and thoughtfully. According to this blog article, the costume designer goes to JJ Hat Center in Manhattan for Matt Bomer's character's hats. And according to yelp, the staff there is friendly and know their shit.
posted by spec80 at 7:11 AM on September 30, 2010

Best answer: The hat is dead. I'm not saying you look dorky in a hat or that hats are ridiculous or douchey or whatever. It's just that the fashion moment/social expectation of hats has been over for a long time. It says, "I am young and experimenting with developing some eccentricities."

I do know some men who can pull it off other than the ones who have been mentioned: old men (like the ones who are old enough to have worn them when they were fashionable), priests, and men in the military while wearing their uniforms.

You can probably still pull off the flat cap, however, just not with a suit.
posted by deanc at 7:15 AM on September 30, 2010 [2 favorites]

"A fedora hat worn by me without the necessary protective irony would eat through my head and kill me." Listen to George W.S. Trow, for he is wise.
posted by escabeche at 7:17 AM on September 30, 2010

Best answer: Mefi's own youngamerican on this issue.

Short version, which applies to hats but also applies to good men's fashion practice generally (and I'd argue good consumerism generally): wear a hat for the purposes a hat was intended for and pick hats which are ideally suited to that purpose. Sunny outside and you need to shade your eyes and/or not sunburn your head? Wear a hat. Raining and you need to keep the rain from getting in your eyes? Wear a hat. Cold outside and you don't want your ears to get cold? Wear a hat.

This suggests that particular hats are suited to particular situations. It also suggests you should never wear a hat inside. Good rules to go by, and a non-arbitrary reason to go by them.
posted by l33tpolicywonk at 7:17 AM on September 30, 2010 [6 favorites]

As foursentences's significant other, and therefore as someone who is seen in public with him, I feel that I should emphasize this statement of his:

Assume I have no fashion instinct whatsoever.

Take this at face value, folks. This is a man who, were such an item available and were I not around to object, would go around in a neon rainbow jumpsuit. This is a man who only recently started hanging up his dress shirts instead of cramming them, unfolded, into a drawer. I'm still trying to get him to stop walking around with his pockets literally bulging with a bunch of crap he thinks he might need one day when, I don't know, he has to defuse a bomb MacGyver-style.

This is not a man who needs to be told "wear what you want to, screw other people" -- he's got that part down. This is a man who needs to be told what his choices in clothing convey to other people. If fashion were a language, foursentences would still be in the babbling stage.

(I say this all, of course, with love and affection. Let's just say I ain't with him because of his sense of style. I also say this as someone without a ton of fashion sense herself, hence my lack of input on the hat issue. I love you baby!)
posted by pluckemin at 7:25 AM on September 30, 2010 [11 favorites]

People don't think as much about you as you do.

I also think that hat-haters secretly wish they had the confidence to wear a cool hat but are too insecure. We hate they thing we secretly desire, right?

I am the Dad With The Hat in my town at soccer games, Cub Scout events, etc. -- but my head stays shaded and my kids can find me easily. And I like it, so I wear my hat (Akubra Cattleman).
posted by wenestvedt at 7:30 AM on September 30, 2010

I used to wear a fedora. Emphasis mine.

I also used to have approximately the fashion sense your S.O. describes. I wore things that...well, that nobody wears, or ever has worn.

I did this because, at the time, I didn't care a whit about what strangers thought of me. The fact that you are asking this question tells me you do care.

So, no fedora. Other hats, YMMV, but no fedora.
posted by AugieAugustus at 7:36 AM on September 30, 2010

Flat cap is fine with regular clothes, but with a suit is questionable. If there is an actual reason to wear a hat, then go for it, but just for style, no. Fedora is an absolute no-go. I am one of many people who have a visceral reaction to fedoras. I think it's because there was an explosion of d-bags in fedoras who wanted to talk in old-timey talk, almost like rockabilly people but a different era, and it's hard to separate normal fedora wearers from those people.
posted by elpea at 7:42 AM on September 30, 2010

I'm not sure if anyone else feels this way, but I sort of feel like when somebody is wearing a nice hat, they're trying to look fashionable. I also feel like people think there's something wrong with TRYING to look fashionable, that it's all supposed to be effortless or else it's cheesy.

But, I mean, I think it's OK to try to look fashionable. And maybe the first few times you wear it you'll look and feel like "SOMEBODY WHO WANTS TO WEAR HATS" but after that you'll just be somebody who wears hats.
posted by smirkyfodder at 7:45 AM on September 30, 2010

I like a man in a hat. You are more allowed to wear a hat in New York than you are in other places, so expect fewer negative reactions if that is where you live.
posted by millipede at 7:52 AM on September 30, 2010

In my opinion, the only people that can "get away" with hats & suits are African Americans and Cowboys (in a different way).

Suit and fedora says Orthodox Jew to me.
posted by electroboy at 8:06 AM on September 30, 2010

Dark suit and matching fedora, that is.
posted by electroboy at 8:19 AM on September 30, 2010

My very dear BFF/roommate dresses this way whenever he has the chance to, is 32, and looks very dashing. Although I'd agree that the flatcap will only go with certain kinds of formal wear -- you might want to branch out in the hat dept.
posted by Narrative Priorities at 8:39 AM on September 30, 2010

I am not that young, early 30s, but live in a college town and watch the young'uns.

Where I live, everyone wears hats. It's cold and/or sunny more often than not, you need a hat here, preferably with a bill.

I think people get a little lost on the subject of hats because many of us have been removed from their purpose. Back when professional men walked to work, they wore hats to shield their eyes from the sun/head from wind. That's why you take them off when you're inside- they are like a coat that way.

IIRC, the reason women were traditionally allowed to wear hats indoors is an extension of the same thinking that gives us the mantilla/hijab/wimple, and then morphed into, "Women don't want to mess up their hair taking a hat on and off".

I find it a little silly when anyone, man or woman, wears a hat indoors, but that's just me. I certainly don't think it's rude or offensive or anything.

I like flat caps on men of all ages. I think they look good with everything except golf attire. The hubs has a nice wool flat cap that is his "dress" hat- it goes with an overcoat and gloves, which he only wears when he's in a suit or something else dressy (like wool pants with a collared shirt and a sweater).

If it's not cold enough for a coat, and you are wearing a suit, I think a fedora would look a hell of a lot better than a ball cap. Justin Timberlake doesn't have to ruin everything.

In closing, I know/knew three young men (one is now deceased, RIP R.S.) who wore/wear suits and hats with regularity. As in, not just for funerals. One was from Portland, OR, one from Boston, and one from Detroit. One Puerto Rican, one biracial (white/Korean), and one African American. All are/were in their late twenties. I never thought they looked anything other than nice. Certainly a lot better than the typical dude in broken in jeans and threadless Tshirt and a faux weathered American Eagle ball cap with some made up business on it.
posted by Leta at 8:41 AM on September 30, 2010

For what it's worth, the first time in recent memory that the thought "Since when did all these people start wearing hats?" crossed my mind was this past weekend in Vegas, at the Wynn/Encore properties.

At both the pool (women, with mens dress shirt over bikinis) and the club (men, with untucked dress shirt, tie, giant watch), the Tribly was strongly present. Not quite at the level of uniform with resulting backlash in frequency - but we aren't that far off.

I'm old and have a kid and never go out anymore, so you may/may not be able to pull this off depending on you, your carriage, and your scene.
posted by NoRelationToLea at 8:50 AM on September 30, 2010

Once I was a little drunk and hanging out with a good friend of mine who is sort of a dork. He's great, but he's kind of a closet MegaDork. He randomly brought up the fact that he had always wanted to own a really cool hat, like a fedora or something. My immediate response was, "Do you *want* to have sex with women?"

This was more relevant in his situation than yours, since you already have an SO, and obviously there are women in this thread who are into guys who wear hats, but the truth is that a hat is one of those sartorial statements that is very non-neutral. People have strong hat opinions, and I would say that most people have strong negative hat opinions. You need to decide if wearing a hat is important enough to you to risk turning off a certain proportion of the people you meet.
posted by MadamM at 9:08 AM on September 30, 2010

Always remember that a hat is intended to keep the weather off your head and should be removed while inside.

posted by KokuRyu at 10:22 AM on September 30, 2010

Best answer: As a rumpled older man whose fashion instincts, while fairly keen (my wife might disagree), tend to be weaker than my laziness and general tendency toward wrinkly, stained, and cat-hair-covered clothing, I proudly wear hats throughout much of the year. In winter I wear hats to keep rain and snow off my head; in summer, I wear hats (much less often) to keep the sun off my head.

I collect compliments on my hats constantly, and I am extremely sexy in them. (That second item may be a slight overstatement). I think the key is: they're useful articles of clothing, then they're fashionable. You have to be a little picky, and it has to get broken in properly. Don't wear things just because you think they're stylish, in theory. They have to actually look good and be comfortable enough to really be pleasant to wear. Like any other article of clothing.

As for people who disapprove of what you or I or anyone else wears, regardless of what it might be: they're losers. Why waste energy caring what they think?
posted by Erroneous at 10:50 AM on September 30, 2010

Wear whatever makes you feel good, dude, and fuck the haters.

But seriously, hats are cool. And if you want to feel comfortable and accepted with a flat cap, go to Yorkshire. You'll have to hang out in old geezer pubs, though :-)
posted by Decani at 11:37 AM on September 30, 2010 [1 favorite]

what's wrong with tucking your shirt in your underpants NOW?
posted by 3mendo at 11:47 AM on September 30, 2010

Wear the hat like you mean it. Consider a derby (bowler) instead. It shows a little more thought than a trilby or a newsboy cap. I like wearing mine.
posted by monospace at 12:25 PM on September 30, 2010

Best answer: This is not your fault, but if I see a heavier dude in a fedora or trilby my first thought is that he reads books about elves, with dragons on the cover, exclusively. It's just how it is. The thing has a cache nowadays which is unavoidable. On the upside, you'll be able to pull it off when you're older.

A flat cap is fine for everyday wear but should be removed when inside. I have known people who treat a hat as a key component of their personality (thus insisting on wearing it indoors), and to a one they are unwittingly correct, because they are boring people.

If you have no fashion sense to speak of, then consider this: The fact that other people are wearing a thing successfully is no reason to try it yourself. The people who are generally known as fashion plates are the people who won the genetic lottery, and just sort of look good wearing anything at all. Johnny Depp looks good in a fedora, but would also look good in a sombrero and boiler suit. Again, that's just how it is.

But here is something you may find useful: A nice hat will go with a suit much better than it will with anything else. If I see a guy in a fedora and khaki shorts, I think he collects swords. If I see a guy in a fedora which matches his suit and tie and coordinates well with his overcoat, I think he's got it going on.

So you can probably pull it off if worn with a suit and in colder weather. Putting on a hat to go outside in the summer is not on.
posted by FAMOUS MONSTER at 12:47 PM on September 30, 2010 [1 favorite]

My husband and I have a friend, E. (he's 38). He loves to shop, loves clothes, and loves his wife. They're both very quirky, fashion-wise. E. has been known to wear a suit with a hat, on more than one occasion. He also rocks the flat cap and ascot. Yes, ascot. He totally owns all of it, too. He's not a hipster, he's not an asshole, he's not trying to hard. He's just E. It's who he is. Seeing him in shorts might kill me. E.'s wife can absolutely get away with wearing a sequined dress to dinner. They're just from a different time, you know?

What I'm saying is, if who you want to be is a guy who dresses quirky and wears hats, go for it. But go all in. Own it.
posted by cooker girl at 12:47 PM on September 30, 2010

For what it's worth, the first time in recent memory that the thought "Since when did all these people start wearing hats?" crossed my mind was this past weekend in Vegas, at the Wynn/Encore properties.

At both the pool ... and the club (men, with untucked dress shirt, tie, giant watch), the Tribly was strongly present.

QFT. Many clubs in Vegas go so far as to have a little fedora store right outside. Hats were cute in the early '90s, when everyone was trying to be anachronistic. Now they're just trying a little too hard to be hip like Justin Timberlake or [name your throwaway 20-something actor here].

That said, if you actually MUST wear a hat, at least make it a flat one (IF you can pull it off!) -- you'll look slightly less like you're trying to be every vacationing fratboy in the universe.
posted by coolguymichael at 1:48 PM on September 30, 2010

Best answer: I am SO glad I live in Oakland where people appreciate a good hat and don't interpret it as "trying too hard" or "wannabe pick-up-artist". I wear a hat every day and have people coming up to me trying to buy it off my head. There are few things as good for one's self-esteem as having a total stranger approach to say "Now that... is a hat. You look sharp!"

OP, are there any good hat stores in your area? Since you don't feel confident in your own fashion sense, I'd suggest asking the salesfolks at a good hat store for their advice. In case you're anywhere near Oakland, get yourself to the Hat Guys at Broadway and 17th Street, downtown. Wonderful store. The first time I went there, I walked in and said "I want something that's part riverboat gambler and part Argentinian gaucho, with very little 10-gallon-hat." The guy thought for a few seconds, pointed to a hat on the back wall, and said "That one." He was right.

Find somebody whose judgment you trust. Pick a hat that you think looks good that they agree looks good on you. Wear it. Love it. Own it as yours.

And some of the comments in this thread... "Don't wear a hat to go outside in the summer." Say what? It's a hat. Part of its purpose is to keep the sun off one's face. "Flat caps don't look good on anyone over 23." Bah.
posted by Lexica at 2:01 PM on September 30, 2010 [3 favorites]

if who you want to be is a guy who dresses quirky and wears hats, go for it. But go all in. Own it.

This is absolutely true. Don't half-ass an affectation, because then it will be obvious that it is just that. Own it, make it a part of you, and be consistent. If this seems like a lot more work than it's worth, it's not for you.
posted by splatta at 2:11 PM on September 30, 2010 [2 favorites]

tl;dr but

there's no way that (wearing a flat cap) plays after age 23 or so.

Actually, I began wearing flat caps (aka newsboy, driving cap and the cheese-cutter) in my early 20s. I'm in my late 50s now. It certainly "plays" on my station.
posted by Rash at 2:26 PM on September 30, 2010 [1 favorite]

Response by poster: Thanks for the outpouring! The middle ground I'm getting from this is: a high-quality hat, chosen by experts, matched to nice suit and coat, worn in moderation and without ostentatious hyperconsciousness, and removed indoors, will raise some eyebrows but not roll too many eyes.

I'll reform the rest of my wardrobe, lose some weight, then go consult an expert haberdasher and buy conservatively if at all.

I appreciate the advice!
posted by foursentences at 6:35 AM on October 1, 2010

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