In Character: Van Wilder

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Ok, no, this is not a GOOD movie—and not just because Tara Reid is the most serious thing going here. But if you’re looking for a rainy-day excuse to spend a few hours with your couch and Ryan Reynolds? Well, it’s as good as anything going. Also: College-boy dressing in 2002—something to behold. —erica

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A Zanerobe shirt that eventually gets him lei’d.

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An Alexander McQueen chain wallet that makes the frat brothers of DIK especially nervous.

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A Saturdays hat, worn backwards to convince Taj to go for Naomi (“That’s ‘I moan’ backwards.”). 

More, more, more “In Character!”

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Weather Vain: Birmingham, Alabama - 94 and Clear

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If you’re in Birmingham today, maybe carry around a personal A/C unit? How to survive a Heart of Dixie sweat fest. —erica

Clockwise from top left:

+ A Suno dress that’s juuuust a little Fried Green Tomatoes.

+ Sandals, from Charlotte Stone, ready for some dancing at Zydeco.

+ This Otaat/Myers Collective wristlet—nearly as enticing as a piece of Johnny Ray’s pie.

+ Collette Ishiyama earrings that would fit right in with the finds at Table Matters.

+ A Sensi straw hat that’s your best shot at staying cool—at least until it’s time to head to The J. Clyde for beers.

For more thoughts on how to deal with the heat, head here.

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In Character: Daniel Desario

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In 1999, Judd Apatow and Paul Feig gave us James Franco. No matter how you feel about that 15 years later, you’ve gotta admit that dude was pretty stellar on Freaks and Geeks. He was the king of the burnouts and best bud to Nick Andopolis—a character played by Jason Segel, who, BY THE WAY, also made his debut on this show. Bam. —erica

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Wearing this Lynn & Lawrence hat means not having to shower. Right?

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A Rag & Bone henley in an earthy neutral—freak wardrobe essential at McKinley High School.

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A rumpled Carven shirt that Kim Kelly would totally borrow-slash-steal.

Get more o’ this business. A whole lot more.

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Couple Up: Andre Agassi and Brooke Shields

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Andre and Brooke were a total curveball—ok, that’s the wrong sport, but you know what I mean. People is better at this than I am: When the two divorced in 1999, the mag titled its story “Double Fault.” Ah, there it is. Here, a look back. —erica

Andre Agassi: Silver hoops from Simon Sebbag, a T by Alexander Wang windbreaker, and a sweat-proof Huf hat.

Brooke Shields: Way-classic Super sunglasses, a polished Blk Dnm blazer, and coordinating silver hoops by Alexis Bittar.

More couples who once were!

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Of a Kind

Doesn’t this Brookes Boswell hat look like it’s ready to be besties with an umbrella drink? —erica

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Next Level: Straw Caps

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Fedoras and Panama hats get plenty of love, but these days, straw *caps* are looking for a little attention, too. Ready to get your head in the game? —erica

LEVEL I: Clyde goes so freakin’ minimalist.  

LEVEL II: For a more ladylike, almost cloche effect, go with this Henrik Vibskov sucker.

LEVEL III: The rope detail of this Eugenia Kim one = very Overboard.

LEVEL IV: Not quiet, this Reinhard Plank take. But it’d be pretty sick with a tank dress and Chucks, if you ask me.

If you’re looking for more “Next Level,” let me show you the way…

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In Character: Puss in Boots

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Personalities deserving of their spinoffs: Lauren Conrad, Wolverine, Flavor Flav, and Puss in Boots. I mean, that cool cat obviously knows how to accessorize. —erica

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A Janessa Leone hat that can be clutched to sell that whole I’m-just-a-sweet-kitty act.

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An Isabel Marant belt, ready to hold a sword that’s almost as big as he is.

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Over-the-knee boots from Alexander Wang that Donkey’s likely jealous of.

More of this! Here!

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In Character: Billy Madison

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Graduation season is upon us. And if this was 1995, we’d all be patting Billy Madison on the back for passing 12th grade (well, all the grades, really). Below, how to cop his back-to-school look. And if this isn’t enough for you, check out this tribute from Four Pins—it’s for real. —erica

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A Marweather hat that rules. Just like O’Doyle.

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A preppy-as-they-come Band of Outsiders sweater—with the sleeves ripped off, for better golf-carting.

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A baseball jersey, from Opening Ceremony, that the hot third-grade teachers gotta respect.

Whoa, so many more “In Characters.” Have at ‘em.

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Couple Up: Cindy Crawford and Richard Gere

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Most photos of Cindy Crawford and Richard Gere involve her wearing a cut-down-to-there dress and him done up in suit. (Oh, and there’s also this Herb Ritts shoot for Vogue in 1992.) Turns out, these two did go places together that didn’t involve a red carpet, though, and when they did, it was kind of hilarious, outfit-wise. —erica

Cindy Crawford: A cross necklace by Alexis Bittar, a floral Minkpink skirt, and the perfect denim jacket from Current/Elliott.

Richard Gere: A loud Huf hat, a sweatshirt (thrown over the shoulders) by Todd Snyder for Champion, and dark-as-they-come Super sunglasses.

Lookin’ for more throwbacks? You’re in luck.

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Weather Vain: Baton Rouge, Louisiana - 76 With Thunderstorms

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Like Garth Brooks, I’ve gotta send my love down to Baton Rouge. Here’s an outfit made for a day like today. —erica

Clockwise from top left:

+ Ready for dancing at Teddy’s Juke Joint? Cause this cotton Ulla Johnson dress is.

+ To protect that head of yours in case of a downpour: a white leather Etudes cap.

+ A K/LLER necklace fit for deviled eggs and crayfish at IPO.

+  A slick Louise Goods clutch, the color of a pint of Abita Purple Haze.

+ Dream Collective earrings—to hold you over until the April showers bring May flowers?

+ The most grown-up take on a jelly sandal ever, c/o Madison Harding.

Whoa, when it rains, it pours: Check out all of our “Weather Vain” posts.

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