How To Wear A Hat

A hat is  likely the most under-used accessory a  woman can wear, and especially for crossdressers as it conceals a large head while adding distracting but beautiful elements to your face. And hats are most certainly the forgotten accessory as you can see in this post on TG Forum.  Hats range from the pillbox made famous by Jackie Kennedy to the large floppy hat ever popular today. And don’t forget those large fur hats that add elegance to your winter wear or bejeweled and feathery fascinators that add incredible interest to the women wearing them.

But where to start: your face shape. In this video, Marilyn Hellman talks about the five general face shapes and the types of hats that flatter those faces. Marilyn is the owner of Marilyn’s (Distinctive European Fashion Boutique) located in Naples, Florida. This video is a great “how to” tutorial on how to choose a fashionable hat to enhance your own individual beauty.

Today’s most popular hat is an oversized hat which is a great way to cover up in the sun (and look really chic.), but there are definite Dos and Don’ts for wearing a big hat.

Don’t Wear a Hat That’s Too Big.


Charles Eshelman/Getty Images

Big hats may be the hottest look in fashion but that doesn’t mean that just any size will do: there is such a thing as having a hat that’s just entirely too big, like Donna Karan’s.

What we do love about Donna Karan’s look is that she wears her hat with complimentary neutrals for a finished head-to-toe look.

Do Wear an Oversized Hat in Proportion to Your BodyAudi At The Foundation Polo Challenge hat

While Nicollette Sheridan’s hat is definitely oversized, it still looks in balance with her body. She wisely chose a fitted dress that showed off her fit figure and kept the outfit neutral to make the hat stand out. She has the height and shoulder width to carry off the big hat without looking like the hat is wearing her.

"Life Happens" Special Screening hatDon’t Let the Big Hat Wear You.

Alice + Olivia designer Stacey Bendet wears a large red hat that overwhelms her look and makes her entire outfit look costume-y. While we love color in hats, the combination of scale and bright color (in addition to being worn with a print and matching red belt) just make it all too much look

Do Wear a Big Hat to Ground a Print. Hat -Seen Around Lincoln Center - Day 7 - Spring 2012 Mercedes-Benz Fashion Week

Rachel Zoe wears a wide-brimmed hat that fits her petite frame just fine; she also uses the oversized hat to ground a floral print hat. It works because the base colors of everything are monochromatic (black) so the effect is sleek.

hat - alice + olivia By Stacy Bendet Hosts The Preview Of The Kelly By Kelly Killoren Bensimon Jewelry CollectionDon’t Overdo Your Outfit with Big Hat.

Polka dot shoes, sheer skirt and major necklaces? Each one of these elements are intense enough on their own, but combined with the floppy hat they are just too busy on designer Stacey Bendet.

Do Wear a Floppy Hat with a Simple OutfitProject Ocean Launch Party hat

Skip the maxi dresses, frills and piles of accessories with the floppy hat and go for a cleaner look like Tali Lennox does with her short wrap dress and floppy hat. Remember that the floppy hat itself makes a big statement, so don’t overdo the rest of the look.

The Academy Of Motion Picture Arts And Sciences Tribute To Sophia Loren and hatDon’t Be Too Matchy-Matchy with Big Hat.

White go-go boots, white fur, white dress AND a big white hat? Too matchy-matchy (and not in a good way) for Linda Ramone. While head-to-toe black can work with a big hat, almost every other color looks like too much of a good thing when you add a matching hat. If you like a tonal look, try mixing different hues of the same color together, like different shades of brown (chocolate, taupe and cream).

Do Wear a Casual Floppy Hat. Charlotte Ronson & Sephora New York Dinner hat

Skinny jeans, casual tee or sweater and a floppy hat: one of our favorite looks for hat wearers. Dani Stahl keeps the groovy floppy hat casual with her jeans look. Skinny jeans also look great tucked into tall boots and paired with a floppy brimmed hat.

Veuve Clicquot Polo Classic-VIP Marquee hatDon’t Dress Like a Witch.

A floppy brimmed black hat with all black clothing (especially a long black skirt?) It borders on a witch-like look for fashion designer Catherine Malandrino. Big floppy hats are a fashion statement all their own and work best with clean-lined simple clothing. We would’ve loved the big black hat with simple skinny jeans and a black shirt.

Do Go Ladylike with a Big Hat.

The big floppy hat is a great casual look, but the more structured styles can also look amazingly ladylike, like Evan Rachel Woods’s big hat. Complete your ladylike big hat look by pairing it with something distinctly feminine like a bowed blouse.

Here are some more tips on wearing a big hat stylishly, although ignore any advice on keeping it black. Follow the examples here and check out our Pinterest board on Hats Make The Difference.

Reprinted from Nellis

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