Jana Kramer always hits the fashion mark, whether she's on the red carpet or performing a live show. She is what she calls a "classy bada--" (we agree) who isn't afraid to play with new styles and wear very, very high heels. Before the 2014 CMA Awards, the 'Love' hitmaker let us go behind the scenes with her while she got her glam on.

When it comes to Country Music's Biggest Night, Kramer doesn't go in alone -- although she clearly has the fashion sense to do so. She works with Kelsey Deenihan, her hair and makeup artist, who adds to the singer's natural beauty. She's also got stylist Lo VonRumpf, who hooks her up with the season's hottest fashions while expanding her personal style. Kramer and VonRumpf worked together to pick the gorgeously feminine princess gown she wore to this year's awards show, which actually was a different look for her.

"For me, it’s just something I feel comfortable wearing,” Kramer says about her red carpet preferences. “I always like doing something that’s a little bit different, something that I haven’t done before … I wanna be a fashion icon in country."

Kramer works with her talented to stylist to create something memorable, putting her well on her way to becoming that icon. “He knows that each time, I want to do something that’s like a ‘wow’ moment,” she says, adding that she and VonRumpf have been successful each time they've worked together.

For the 2014 CMAs, the songstress went "sophisticated." She and her stylist are usually in different cities, so they rely on photographs and FaceTime fittings to pick the perfect dress. Ah, the beauty of technology!

They don't always agree, however. “Well, there’s a lot of times where he’ll send me dresses and I’m like, ‘I don’t know what the heck you were thinking. This is God-awful,’" Kramer admits, "but he’s always wanting me to expand my style, especially with this dress, too. I did not want to try it on."

"I just have to trust him," she adds.

VonRumpf even let us in on his thought process for styling Kramer, from her jewelry, to shoes, to the gorgeous gown. He started working on this incredible look five months prior to the awards!

“Usually, I’ll create like a storyboard and then we’ll narrow it down to a look and feel," he reveals. "For her, I know the silhouette that will look great on her and the shape and then I try to pick the color of the season."

They waited to pick out her jewels last, thinking about the perfect bling while listening to the calming sounds of Michael Buble. VonRumpf notes that usually, Kramer goes for dainty rings and accents. This year was no different.

We don't recall anything but pure grace and style, but Kramer insists she had a terrible dress at a past ACM Awards event. Then, she had a fashion mishap at the 2013 CMA Awards. "Last CMAs, my dress fell," she remembers. "The belt kept coming off, but it made the dress look really bad." As she walked, the dress would drop down more and more.

Naturally, hair and makeup are a huge part of prepping for the CMA Awards. Kramer worked with Deenihan to get the perfect look for her Badgley Mischka couture gown this year. “We just want to go soft,” she says. “The dress is so pretty, I just wanted it to be simple and soft."

The singer dishes that she carries a small survival kit in her bag, which include necessities like a cell phone, lipgloss, powder and oil blotting sheets. Though while eyes -- and lenses -- are on her during her red carpet walk, Kramer looking elsewhere, taking in other artists' ensembles.

"Jake Owen has some really cool suits that he does," the singer says. "Miranda, I always like to see what she’s wearing, and Carrie because I think she’s just a goddess."

As Kramer was getting the finishing touches on her makeup and hair, she revealed she'd be bringing her tall (and very handsome) boyfriend along as her date to the 2014 awards show. He too got a little help from VonRumpf when getting dressed.

“Lo also styled him to make sure he looks all extra cute,” Kramer explains of her man's Ralph Lauren suit with Kenneth Cole accents. “We’re coordinating, and he’s going to look super handsome.”

She was right. Her boyfriend arrived at her hotel room as charming as a prince, but he couldn't take his eyes off of his beautiful girlfriend. Her other favorite accessory besides the man on her arm? The shoes!

“Honestly, I hate wearing heels," she admits. "On stage I wear them, but usually I wear the ones that are comfortable that I can run around in. For events like this … you just have to suck it up. By the end of the night though, I’ll make my boyfriend give me a foot massage. It does hurt, but I brought a pair of Jimmy Choos in case the Badgley Mischkas are too uncomfortable.”

In the end, Kramer paired her couture gown with the matching strappy Badgley Mischka heels. VonRumpf says her ability to rock sky-high heels are part of what makes her a favorite client of his. She never complains about the height of stilettos, and he says, for a stylist, that is "awesome."

Together, Kramer, VonRumpf and Deenihan put together the beautiful red carpet look that made Kramer appear the true country queen that she is. The 'Love' singer was one of the most beautiful at the 2014 show -- the simple, yet elegant hair, the perfect makeup, the gown that fit her like a glove ... it's easy to see why Kramer is always one of our best dressed!

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