The country superstar tells PEOPLE exclusively that she and her stylists, Marina Toybina and Courtney Webster, wanted the wardrobe to feel "timeless and elegant"

By Hanna Flanagan
Updated December 11, 2020 03:55 PM
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Underwood in Nicole + Felicia Couture.

Carrie Underwood is giving us plenty to celebrate this holiday season.

Earlier this month, the Grammy winner, 37, performed beloved classics and original songs from her first-ever Christmas album My Gift during her highly anticipated HBO Max Christmas special (streaming now) that premiered on Dec. 3.

Entitled My Gift: A Christmas Special from Carrie Underwood, the program also featured special guest John Legend, a cameo from her 5-year-old son Isaiah and eight (yes, eight!) shimmery holiday looks. Underwood tells PEOPLE exclusively that she and her stylists, Marina Toybina and Courtney Webster, wanted the wardrobe to feel “timeless and elegant.”

Underwood in a Nicole + Felicia Couture strapless gown.

"We really wanted this special and my album to be something that people would return to year after year and not feel dated," the country queen says of the inspiration behind her back-to-back ball gown moments.

Underwood in an Elie Madi off-the-shoulder ombré gown.

And while she loved all eight looks, Underwood admits her favorite was the gown she and her team refer to as "the angel dress" — a plunging Nicole + Felicia Couture tulle design that featured statement shoulders and a thin jewel-encrusted belt. "It was perfect for where we had it in the show, and I did feel like an angel in it!" the Cry Pretty singer says.

Underwood in the Nicole + Felicia Couture "angel" gown.

Underwood also donned gowns from Diana Couture, WONÁ Concept and Elie Madi, and throughout the special, she made sure the fashion accurately reflected the music.

"The short dress with the fringe was an absolute must for the show opening, 'Favorite Time of Year.' It was so fun and playful, just like the song," the Storyteller artist explains. "We gave a lot of thought to the overall look of the special and how the gowns and sets really showcased the music."

Underwood in a Nicole + Felicia Couture fringe mini dress.
Underwood in a WONÁ Concept gown.

When asked about collaborating with Toybina and Webster on the Christmas special, the star says, "They always bring the glitz and the glamour…and then add a little more!"

Underwood continues, that after years of working together for red carpet events and award shows, she knew she could trust the styling duo with a project as special as this one. "They have great taste and they know what I like and can bring what I have in mind to life," she says.

Below, Toybina and Webster open up about the inspiration behind each look, capturing Underwood's vision and putting an entire wardrobe together amid the coronavirus pandemic.

Underwood wearing a Diana Couture top and skirt.
Underwood adds a cape to her Diana Couture look.

The looks in the special are gorgeous! What was your inspiration for choosing voluminous ballgowns?

Toybina and Webster: "How could you not go for the ballgowns when you have the opportunity?! Seriously though, usually for her performances she’s moving all over an awards show stage, or traversing long catwalks and going up and down lifts in giant arenas on tour. So we don't often get to have ballgown moments simply because the amount of movement doesn't allow for it. The fact that it's her special with so many iconic Christmas songs — many of them ballads — made it feel like the perfect time to break out these giant confections of tulle and sequins that would never really be appropriate for any other event."

Tell me about the process of working together with Carrie. Do you send her a lot of options? Do you schedule multiple try-ons and run-throughs?

Toybina and Webster: "We sent a few photos to let her know the overall vibe we were going for, but generally she trusts us to bring things we know she'll love. We really get down to business at the fitting. After so many years, we’re pretty good at predicting which pieces she'll end up in, but we always bring a variety of things we know will look great on her. We don't pigeon-hole ourselves by committing to certain looks before the fitting, we want to make sure we really exhaust every option before making the final decision.

Carrie is really in tune with the creative process. She has a defined sense of style and knows what she likes, as well as what will make sense with the screens, lighting, blocking etc. She knows exactly what she needs to make her performance the best it can be, and she trusts us to execute that. She’s also not afraid to take risks and make departures from the original creative direction if the look just feels 'right' to her.

After alterations are done, we’ll have a second fitting to check and make sure everything is in working order, but other than that, any last-minute tweaks we can typically sew right on her."

How did you go about doing fittings and run-throughs amid Covid? Did you have to alter the way you usually work?

Toybina and Webster: "Everything has changed since the pandemic. Before we even got to the fitting, we worked with showrooms to pre-select options as best we could. Of course it always comes down to how things look in person, and often images just don’t do pieces like this justice, but we did our best to limit our interactions by going with our gut from the lookbook images. Happily, many of the gowns from our initial selections ended up being hero looks for the special. When you know, you know! We also all were tested multiple times in the lead up to, as well as days of the shoot. We’re so grateful that productions are taking it seriously and doing their best to keep everyone safe."

How many dresses did you source for Carrie to choose from?

Toybina and Webster: "There were about 12 racks of dresses, so a lot. Some of these gowns were so big they didn’t even fit on the racks, so they kind of just stood up on their own in the middle of the fitting room. We kept things organized by color, then silhouette. There was at least one rack for each color of the rainbow, so it was a lot to tackle. But we tried on pretty much everything to make sure we left no stone unturned."

Were there any looks that almost didn't come together? 

Toybina and Webster: "We’ve got things pretty streamlined at this point! Knock on wood, but we are pretty good at avoiding wardrobe malfunctions. The most complicated look was probably the red skirt, top and matching cape. We had to do a lot to customize it, like adding faux fur trim to the cape, reshaping and rebeading the top. Also a couple of days before we shot the red look, we decided it needed a different, wider waistband. So we had to rush to find a matching velvet, make a belt and create a beading pattern that tied in with the top. But it all turned out perfect in the end!"

What was the best part of working with Carrie and styling the Christmas Special?

Toybina and Webster: "We really love how much trust Carrie puts into the people she works with. She knows that everyone on each project is at the top of their game — just like her — and she lets each department showcase that. She’s not afraid to voice her opinion, but she’s also willing to listen to everyone else’s. It’s truly a collaboration!

The best part of this project was working with a group of people that really allowed us to run with it. We always do our best work when all of the departments trust each other to execute. Carrie, her management, the director, producers, lighting, set design — the whole team came together to make this happen. It’s one thing to see a dress on a rack — it’s an entirely different experience to see the sparkles come alive when the lighting and camera angles are just right, and everything is popping against gorgeous visuals on the screens and ornate decorations on stage while she belts out a high note!"