1. Spying on your man in church. You never know when pulling a Carrie Bradshaw and spying on your own Mister Big is going to take you into God’s house. Make sure you’re prepared with wrist gloves and a Sunday hat that will knock his mother off her pew. For a colorful, sophisticated look, try Linea Large Brim Spikey Feather Hat, Nordstrom ‘Drama’ Wide Brim Straw Hat and Kaliko Bright Pink Straw Bow Hat.

2. Cruising on a doomed ship. Vacationers on the Titanic didn’t know about their impending fate, so they were all riding the fabulous high horse. But you don’t need to choose a sinking ship to look as remarkable as they because these fine boating hats will do just fine. For a more traditional look, try the Linea Stripe Bow Tilted Hat or John Lewis Women Stripe Floppy Hat with Bow. If you want a modern take for your summer boating adventures, Vans I’m on a Boat Straw Boater and Eugenia Kim Honey Striped Toyo Sun Hat are great options.

3. Shopping. A lady would never have entered Tiffany & Co. without a hat in Audrey Hepburn’s day – how slovenly! Channel your inner socialite while perusing the Goodwill by covering that risque head of yours. Either the Louis Vuitton Mink Bell-Hat, Vintage 1960 Black & White Sparkle Bow Cloche Hat or Brenda Lynn Audrey Hat will do.

4. At the doctor’s office. If anyone knows how to seduce, it’s Sophia Loren, especially when she is after a man playing hard to get. You too can feel sexy and chic getting your yearly check-up by channeling her look ala The Millionairess. These will all look fabulous with your corset: MARKET Red Floppy Hat, Brenda Lynn Milan Boater Hat, French Connection Spice Blush Floppy Hat and Nordstrom Floppy Ribbon Sun Hat.

5. Boozing. Hats, headbands, it’s all the same in casinos and speakeasies. Breaking boundaries with nonpareil style, flappers knew how to look fantastic while drinking the Devil’s elixir. Though not quite hats, these hairpieces will get you the look and the swagger. Try Colette Malouf Mesh Puff Flower Crocodile Clip, Zara 1920s Style Headband, Dorothy Perkins Brown Feather With Bead Centre Stretch Headband or Mother Plucker Red and Purple Side Feather Headband and get your drank on.

6. Mourning the loss of ruined winter shoes. It happens to us every year in the land of snow, sleet and freezing rain. We sacrifice a pair of shoes to keep our feet dry and warm. Although tragic, you can mourn your favorite defunct footwear in style by channeling superstar mob wives like Carmela Soprano, Sandra Corleone and Rosalie Aprile. Black and dramatic is the way to go with styles like these: Misaharada Valeska Hat, Comme des Garçons Bow Detail Hat and Lanvin Swarovski Crystal Pin-Embellished Straw Hat.

7. Frolicking and/or walking on water. Wouldn’t we all love to live in Mary Poppins’ wonderful world of animated fantasy? The answer is obviously yes. And although this may not be possible in a city as grimy as New York, you can still frolic about, wherever you are, in a bonnet of fantastic allure. Kokin White Rose Feathered Silk Hat, Bonnets 1870′S Bandeau Hat and Vintage Vine and Big Blossom Straw Hat will have you flying high like the whimsical Poppins herself.

Ladies, how do we feel about this?

LINKAGE: Popgloss via KidGQ