Portland has a tenuous relationship with Italian food.

Aside from notable exceptions like Nostrana, Renata and Ava Gene's, it's not exactly a cuisine most associate with fine dining. But that hasn't stopped luminary chef Vitaly Paley from giving it a go with his fourth venture, Rosa Rosa, which promises an upscale take on classic, "New York-style" Italian. It delivers on that promise to some degree—but that probably won't be what brings guests back.

Located on the first floor of the Dossier Hotel, Rosa Rosa joins the flurry of ambitious eateries that have coincided with Portland's recent hotel boom. If it's a dramatic, upscale experience you're after—and who could blame you, considering the celeb-chef cachet Paley acquired with Imperial and the seafood-forward Headwaters, located up the street at the Heathman—you'll feel most at home in what Rosa Rosa has dubbed "the backroom." It's here chef Kenny Giambalvo carries on his reputation as an accomplished craftsman of hearty, New York-inspired Italian fare that he left behind at the shuttered Pazzo Ristorante. It's a fairly standard white tablecloth and gold leaf affair, with a sommelier buzzing about and a menu replete with fancified takes on Italian standards, like spaghetti carbonara ($17.75) and a wonderfully tangy and garlicky braised lamb shank ($34.50).

But the main room is where the most fun and dynamic items can be found.

As the story goes, Paley's inspiration for the rest of the menu was a trans-Mediterranean jaunt with his partner, Kimberly, in which the two dug deep in Turkey, Georgia and beyond for regional delights they knew would work in the Northwest. Among the glistening marble floors and dramatic wood columns, you'll find a host of vibrant dishes that carefully balance bitter and sweet flavors.

The most exciting on our visit was Georgian chicken chkmeruli ($18.50), a press-grilled slab of chicken seasoned with a simple mixture of garlic, butter, cloves and blue fenugreek that Paley learned about at the Hotel Zuzumbo in Telavi. Paired with a mezze platter ($14.75), which features a smooth and sweet green chickpea hummus, and the Rosa Rosa bread ($5), which is highlighted by a light and fluffy spinach and cheese boyo, you'll have covered most of the flavors Paley brought home with him from his trip.

Perhaps the biggest contrast between the front and back rooms is the attitude, which is noticeable in subtle, Wes Anderson-esque aesthetic tics. In the main dining hall, the menu font is some derivative of Futura, and the small doodlings of goat heads, roses and hands clinking wine glasses look more like the art you'd find on the T-shirt of a tattooed regular at Sandy Hut. In the context of the high-end hotel dining scene, this a bold and smart move for Paley. In a market inundated with restaurants that are stridently classy, it couldn't hurt to tone it down a notch and offer a middle ground between Imperial and the plethora of more lowbrow options. The gulf is as wide as the Mediterranean itself, but Paley does a commendable job filling it with food that's as interesting as it is fun and approachable.

That approachability is bolstered by Rosa Rosa's happy-hour menu, which contains bite-sized renditions of its greatest hits at crazy-low prices. There's the aforementioned chicken chkmeruli, available in kebab form for just $5, as well as a pair of boyos ($4), an à la carte order of pita and hummus ($3.75), a lamb kebab ($6.50) and a lamb meatball slider adorned with tzatziki, sour cherries, sumac and shallots ($5.50).

The drink list features a pair of classic Italian cocktails on tap: A Night in Tunisia ($12, $8 during happy hour), which balances the citric tang of gin with campari and coffee beans, and the 750 Spritz ($10.50, $6 during happy hour), a twist on an Aperol spritz that loses none of its brightness or charm from being kept on draft. The bulk of the cocktail list plays to similar bittersweet sensibilities, with the Upgrade PDX ($9.75), combining amaro, cranberry shrub and a porter from Royale Brewing for a sour, smoky after-dinner drink, and the Storm's a Brewin', which doses a tequila-based tiki cocktail with a top layer of Fernet-Vallet from Mexico.

Despite the panoply of unique Mediterranean fare offered up front, you'd be remiss to skip a few of the standbys entirely. The backroom menu is available in the front after 5 pm, which means you'll have access to excellent dishes like the tre colore salad ($12)—a blend of bitter endive, radicchio and romano that dazzles the senses with a sweet and airy aged balsamic—or the polpo alla griglia ($15.75), a lightly charred octopus tentacle with a pleasingly acidic glaze of preserved lemon that harks back to Paley's strongest dishes at Headwaters.

If you're craving pasta, go for broke with Rigatoni & Nana's Sunday Meat Sauce ($21), which contains a quartet of zesty meats in a sweet red sauce atop impossibly soft and fresh rigatoni. It's not the fanciest dish on the menu, but the warm, fuzzy memories it invokes of the first time you enjoyed a simple pile of pasta and sauce are well worth the price alone.

EAT: Rosa Rosa, 750 SW Alder St., 503-294-9700, rosarosapdx.com. 7-10 am and 11 am-11 pm Monday-Friday, 8 am-11 pm Saturday, 8 am-10 pm Sunday.