It's difficult to feel sunglass-savvy these days: between celebrity-driven trends and the constantly changing styles on the market, what's cool today can seem passé tomorrow. Aside from this instability, the simple process of picking the perfect pair is intimidating enough. After all, the right shades have a transformative power and can turn an outfit from playful to glam, or simple to edgy, in a snap. But don't despair, dear readers, finding the right sunglasses might be easier than you think, especially with the staff at your disposal!

As regular readers know, when it comes to sunglasses, we consider ourselves aficionados. Though we obsess about them all year long, we must admit our enthusiasm for the spring crop is particularly intense. In fact, the excitement levels were so high that we decided to skip showing our favourites on a fit model and jumped into the images ourselves! Although sunglasses are like shoes-meaning you can never have too many-we somehow managed to narrow it down to the absolute cutest, most flattering, and on-trend pairs for today's Top Five. From circular styles to eighties-inspired wayfarers, we hope you enjoy our picks. And now, without further ado, here are the shades you must have at this very moment!

1. Benjamin Eyewear Cindy Sunglasses ($325)
Of all the styles we pulled for today's story, the Cindy Sunglasses from Benjamin Eyewear topped everyone's list. Modelled by our resident stylist, Angela, these oversized black frames are incredibly flattering on a range of face shapes. They were inspired by two excellent references: the sunglass-clad ladies in Patrick Nagel's iconic, eighties lithographs and classic Italian frames from the sixties. The results are truly amazing and are sure to add a glamorous oomph to any outfit-no wonder Gwyneth Paltrow purchased this exact pair just last week! Of course, we do have some alternatives for you as well: try Topshop's 80's Flat Top ($30) version for a similar look at a lower price. You also might like the wire-framed style of American Apparel's Highwire Sunglasses ($30) as another option.

2. AJ Morgan Feline Sunglasses ($28)
While the eighties and nineties were big influences on the Spring 09 runways, we also saw the reemergence of classic fifties looks at shows like Giambattista Valli and Michael Kors. Naturally, the decade's shapes and silhouettes trickled down to accessories too, albeit in a modern way. Take AJ Morgan's Feline Sunglasses, for example: they offer a subtle riff on the iconic wayfarer shape-very Talented Mr. Ripley. As seen on Kate, above, the subtly retro style has a very luxe look, especially when paired with a little red lipstick! They're perfect for lots of different occasions: a three-martini lunch, holiday on the Rivera, or even just cruising around town in a sweet summer dress.

3. Vintage Classic by Ralph Lauren Sunglasses ($250, 323.951.9740)
As we mentioned earlier this season, the circular frame is having a major fashion moment. As modelled by one of our wonderful interns, Amy, these Vintage Classic Sunglasses by Ralph Lauren are the perfect amalgam of style and spirit. Handmade in Italy in the eighties, they're of the utmost quality and are just as fashionable now as when they were originally created. The tortoise and wire frames give them a modern and cutting-edge look, even with the round, vintage shape. For a similar look, try Lennon Brown's Leather-Like Small Round ($16) version; they're a total steal.

4. Lanvin #4122 Sunglasses ($295)
Our Top Five needed a dose of Parisian chic, so we included these Lanvin sunglasses, as they give our other editorial assistant, Liza, a certain je ne sais quoi. Although they're not traditional-at least in the Delacroix floor of the d'Orsay sense-this sturdy, circular shape favoured by fashion icons like Mary-Kate Olsen is already a cult classic. Perfectly proportioned, we like Lanvin's version because it doesn't overpower une petite face. Since this style is so à la mode, there are plenty of options that will help you achieve a similar look for less of an investment. Choose from Cheap Monday's Night on Earth Circle Wayfarer ($30), 80s Purple Activist Vintage Sunglasses ($10), or 80s Purple Inventor Round Vintage Glasses ($10), which has the added flair of a flip shade.

5. Karen Walker Duper Strength Sunglasses ($200) in Powder Blue
Our coverage wouldn't be complete without at least one colourful set of sunglasses, so we decided to include this powder blue pair. Modelled by our associate photo editor, Christian, these Karen Walker Duper Strength sunglasses really pack a playful punch! The light blue hue is a fresh update to last summer's clear craze and neon frames, not to mention they're a bit jazzier than classic black. You can never go wrong with Karen Walker-her shades have been seen on fashion savants like Alexa Chung, Jenny Lewis, and Zoe Kravitz. Punky and perfectly cool, they're a highly covetable, super-strong selection!-Liza Kaplan