Hat advice...
April 11, 2008 7:56 AM   Subscribe

Advice/tips for what to look for in a hat... for a man who looks like a moron in every hat he's ever tried on AND looking for a good place to get a man's hat in Toronto.
posted by dobbs to Clothing, Beauty, & Fashion (13 answers total) 7 users marked this as a favorite
I can't help you with Toronto hatters, but in my experience hatters are good at figuring out what will suit your head. Go when they're not busy (which, alas, in these hatless times will not be hard) and be prepared to spend some time overcoming your ingrained "I look like a moron" reflex—try on a bunch and learn to filter out the basic reaction (which will go away as you get used to wearing a hat) from the extra twinge that occurs when a hat really does look terrible on you; maybe take along someone whom you trust to tell you what looks good and what doesn't. As a suggestion, since we're (finally) getting some warm weather, Panamas look good on pretty much everyone.
posted by languagehat at 8:04 AM on April 11, 2008

Languagehat, can you share any basic guidelines regarding hat selections? I've seen a few magazine articles about choosing the right eyeglasses for your face (i.e., rectangular faces should have X frames, while round faces look better with Z frames).

I bought something like a pork pie hat once, and I feel like when I wear it, I look like I'm on Degrassi Junior High.
posted by Admiral Haddock at 8:19 AM on April 11, 2008

You might find some ideas here, but part of wearing a hat is being comfortable with sometimes standing out in the crowd. I second the advice of finding a good hat shop. I bought a nice porkpie for myself, and even though I went in with an idea of what I wanted, the guys at the shop were great at helping me find what actually worked for me.
posted by pupdog at 9:24 AM on April 11, 2008

Cowboy hat. Who doesn't look great in a cowboy hat?
posted by Sassyfras at 9:31 AM on April 11, 2008

There's a great old hat store (haberdasher?) on Avenue Road, north of Lawrence, called The Hatter link is to a blurb from another site.) We lived close to it about 11 years ago. I used to go in there at the time, but hats weren't really "back" yet at the time so I never got anything. I've been meaning to go back there.
posted by chococat at 9:34 AM on April 11, 2008

Rotman's on Spadina might be a good place to check out.
If there's nothing there, the vintage shops in Kensington Market are nearby.

Or just get a Tilley. Hardly anyone looks good in them, but so many people have them, you just blend in.
(Unless you're travelling, then it just screams "CANADIAN TOURIST!!)
posted by Chuckles McLaughy du Haha, the depressed clown at 10:01 AM on April 11, 2008

Yes. If I were you, I'd go to Rotman's and trust their advice.
posted by mumkin at 10:52 AM on April 11, 2008

Good lord, I just paid attention to the asker's name. dobbs?! But you're like languagehat or Hat Maui... you are a hat. I always think of hattery when I see your username, being an occasional Dobbs-wearer myself. Srsly, how can you not wear yourself on your head? If someone made mumkin brand hats, that's what I would be looking for in a hat.
posted by mumkin at 11:00 AM on April 11, 2008

As a new hat-wearer and someone who thought his head was simply not made for hats, I have a couple pieces of advice. I too admired the allure of a proper headpiece, especially after watching many 50s and 60s movies. You're on the right track trying to find a true chapelier, though I don't know of any in Toronto.

What convinced me that I could aptly wear a hat was trying a few for myself. The most important, I found, is wearing the right size. There's an enormous variation in comfort and style between a 58, 59 and 60. My head is a 59, anything else does look silly. You should try measuring your hat size, here's a little guide on how to do it.

As for appearances, I brought along my sister who was a fine companion in the search for a perfect hat. You'll find that some styles just better suit the shape your face. It's a matter of trying them out – that's the most fun part! You should be warned that a good hat, made for instance of good quality felt, will be quite expensive.

I've particularly enjoyed my fancy homburg and sturdy fedora, particularly in the rough weather I recently encountered. I've had only positive reactions. Sadly, today's world is no longer designed for hats. Be prepared for impracticalities when travelling and socializing.
posted by kepano at 11:53 AM on April 11, 2008

Head south of the border to Buffalo, and check out Custom Hatter. Be forewarned: it's in a rough neighborhood, but then again, anytime Canadians get lost in Buffalo, they end up in the same rough part of the East Side, so you should be able to find it with no problem. O'Connell's in Buffalo's University Heights neighborhood is one of the last of a dying breed of "trad" men's stores, and you should be able to find an old-school hat there with no problem; their online catalog is only a small part of their total inventory. Almost everything O'Connell's stocks is made in the US, Canada or the UK.
posted by elmwood at 1:19 PM on April 11, 2008

I've seen a few magazine articles about choosing the right eyeglasses for your face

Of course, these rely on being able to tell what sort of face you have accurately in the first place. The same problem arises for hats, plus body shape and height, style of other clothing, where you live, and probably several other factors all tie into this. A hat shop is the place to get a good opinion on what sort of hat one looks good in. If there's a gay man running the shop, and you are a man, all the better.

Who doesn't look great in a cowboy hat?

Tourists wearing shorts. Especially with cowboy boots. **shudder**
posted by yohko at 4:22 PM on April 11, 2008

Okay, so I hit Rotman's but was disappointed as I was informed that they didn't yet get their stock for the year. The man was terrific there though.

Then I went up to The Hatter and the woman there was great. Very patient. I bought a cheap hat for $20 and brought it to Cuba and pretty much wore it non stop. It's great. I had many locals ask me if I'd sell it or trade it to them. I'm gonna head up there and get a more proper, durable hat next week. I just didn't want to spend big bucks on something if I didn't find I'd actually wear it.
posted by dobbs at 3:46 PM on April 29, 2008 [1 favorite]

I've just had a friend recommend a store in the Eaton's Centre called Big It Up which he says has a great selection of hats--and he was wearing one when he said so. Haven't been in yet but thought I'd mention it.
posted by dobbs at 9:12 AM on May 28, 2008

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