Are You a Hat Person?

Do you wear hats? Though I’ve never claimed to be much of a “hat person,” I’ve certainly worn my fair share of the now must-have accessory of the season. My earliest memories are of my mother stuffing my long hair into an itchy, wool beanie — which matched my equally itchy purple scarf. After graduating from elementary school (and the ever-unfashionable snowsuit), I remember trying to duck out of the house without a hat, positive the puffy rain-resistant hood of my Starter jacket would do just fine (apparently my mother thought otherwise). Then in high school there was my Von Dutch/trucker hat phase — which I probably stuck with almost as long as Britney Spears. And throughout college I experimented with various forms of fedoras and bucket hats.

Now, though it’s the first week in January, I’ve yet to buy any hats this season. (The knit newsboy hat — in the picture — that I bought last weekend on Canal Street out of mercy for my nearly frostbitten ears hardly counts.) And with yesterday’s temperature at a torturous 17 degrees, it’s now clear that buying a hat will have to take precedence over Project Runway reruns — plus, there are great sales on winter wear right now (see below for details). Before attacking the sale shelves at Woodbury Commons, I sat down with local fashion expert Candace Chestnut of Chappaqua to find out just what hat I should be looking for. Candace, a designer of the woven portion of the boy’s line at Gap, Inc. and an adjunct professor of fashion at her alma mater, Marist College, provided all the helpful hints on just how to make it work “up there.”

How should you wear a hat?
How to wear a hat? With confidence! Given the multitude of styles that are out this fall/winter season, there’s something for everyone — from woolen or chunky knit newsboy caps to bucket hats, knit berets, and 1920’s-inspired and equestrian hats.

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In your opinion, which hats are most in style right now?
What’s really huge right now are the chunky, hand-knit berets. They can be worn a number of ways, both indoors and outdoors. Equestrian and 1920’s-inspired hats that have a little bill and a full form are very popular right now — like a refined newsboy hat. Also very “of the moment” are knit and woolen military-inspired cadet hats.

How can you wear a hat as an accessory and not out of necessity?
Hats have really crossed over from something that you wore for functionality to an accessory. They’re no longer worn just to keep your head warm outdoors. People will leave them on when they come indoors. Hats are as integral to an outfit these days as any other accessory; necklaces, earrings, etc. And a lot of hats today are so versatile. They can be worn with anything; you can wear them with jeans and a t-shirt. You can really transform an outfit. For example, once worn on the slopes by snowboarders, the woolen military inspired cadet hats and the afore-mentioned berets can be worn casually with pants or denim during the day and also into the evening with a little embellishment.

Is there anything you’d warn against when “topping off” your outfit?
I would advise people to be cautious when wearing a fedora. I think there’s a level of… Britney/K-Fed that comes to mind. But the fedora is still shown on runways — they’re still out there. So you can still pull it off, but you might look costumey if you don’t do it the right way. They’re tricky. You can wear the fedora as a “going-out-hat.” They’re good cold weather fashion because they’ll keep you warm and also enhance your outfit.

Another thing to be avoided is matching. Like, if you were wearing a cadet hat, you wouldn’t want to wear camouflage. Or, don’t wear a houndstooth coat with a houndstooth hat. You don’t want to match because then it looks a little too contrived. What’s great this season, is that there are so many patterns and colors. There’s so much fun in mixing it up. I like the contrasting — it makes it a little more whimsy. Just have fun with it!

What is your favorite hat right now?
With this fall/winter season being the season of chunky sweater knit dressing, I especially love all the knit hats out now that resemble heavy gauge, hand-knit berets. I wasn’t sure how the beret would look on me until someone showed me how to wear it. I wear it slouched to the back, not to the side, with just about an inch of my hairline showing — similar to a snood from the 1930’s. These hats add just the right amount of attitude to any outfit. In some stylist circles this look is called the Rumer — as in Rumer Willis, who’s been wearing these since the summer.

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Have you seen anything interesting or inspiring this season?
The one thing that I have seen on some people is the headband; it’s like a headscarf. It looks like something you’d see on the ski slopes. But they’re hand-knit, so there’s a bit of a fashion twist. Also surprising has been the evolution of the newsboy hat. I didn’t think they were still going to be in style this season. But the way they look has been transformed. Now, they’re slouchy and made in knits, instead of cotton.


1250 Pleasantville Road
Briarcliff Manor
20% to 70% off on winter merchandise, until stock is sold out

Next Boutique, Ltd.
17 West Strand
50% to 75% off on fall/winter merchandise, throughout January

Kenneth Cole
Woodbury Common Premium Outlets
498 Red Apple Court
Central Valley
50% to 75% off of original prices, through Jan. 16

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Liz Claiborne
Woodbury Common Premium Outlets
498 Red Apple Court
Central Valley
25% to 60% off on selected merchandise, through Jan. 17

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