A Snowy Winter Wedding in Aspen, Colorado

Ask Ashley O'Winter who the better skier is, she or her husband, Hughes, and you'll get a diplomatic answer. "It's technical. Alpine skiing, that's me," Ashley, a documentary producer and interior and event designer, explains. "But Hughes can telemark [an Alpine variation in which the skier's heel comes up] and snowboard, so it depends..." There's little doubt, though, that both of them can hold their own on the slopes.

Skiing is at the heart of the Denver-based couple's relationship, and it was their love of the sport that led them to each other: Ashley and her family were on a heli-skiing vacation at the art of 2011 in British Columbia, and Hughes was staying at the same resort. "My brother Hudson befriended him and introduced him as my 'future fiancé,'" Ashley recalls. "Big brothers can be so embarrassing." But he was onto something. She kept bumping into Hughes around the lodge, "and I became smitten." The feeling was mutual.

After several months of distance while Ashley finished college in Chicago, she moved to Denver to be with Hughes, who works for his family's ski-and-snowboard business. In April 2015, Hughes proposed during an adventure-filled vacation in New Zealand and Australia. Before they'd departed, Ashley's sister Lyndsay, a jewelry designer, had helped him create the ring. His first thought was moonstone, but "Ashley's a bit of a bull in a china shop," Hughes says a affectionately. "So we decided on a sturdier colored diamond." He presented her with the ring and a romantic letter when they were midway through a mountain-biking excursion, and, true to form, Ashley had banged up her legs. "I was bloody and messy, but so excited," she recalls.

The pair quickly settled on a winter wedding in Aspen, Colorado. "It holds a special place in our hearts because, growing up, we both took trips there with our families," says Hughes. They made the most of the location, planning a day of backcountry skiing for friends and family early in the week, and a rehearsal dinner in a remote wooded spot that guests could get to by ski or sleigh. "I think Hughes even took a couple of runs on our wedding day," laughs Ashley.

On March 19, 2016, 145 guests gathered on the rooftop of the Aspen Art Museum just before sunset to watch the couple exchange vows again the background of Aspen Mountain's snow-covered slopes. The party that followed lasted until the early hours of the morning, but, Ashley says, they still managed to make it to brunch at the base of the mountain the next day—"dressed in our ski gear, of course."

For their first look, Hughes O'Winter took a gondola to the top of Aspen Mountain, where his bride-to-be Ashley Sands was waiting. Picturesque scenery was around every turn, with the snowcapped Rockies as a backdrop for much of the festivities.

Vintage ski posters and postcards inspired the couple's custom stationery suite, by Wouldn't It Be Lovely. Monogrammed compasses served as both escort cards and favors.

Wooden welcome boxes bearing the couple's crest included such mountain essentials as sunscreen and lip balm.

Ashley's engagement ring was designed by her sister, Lyndsay Caleo, and her wedding band was from Beverly K.

Ashley carried a bouquet of ranunculus, sweet peas, anemones, jasmine vine, viburnum tinus berries, and olive branches tied with silk ribbon by Aspen Branch Studio.

The ceremony was held on the roof of the Shigeru Ban—designed Aspen Art Museum. Bare aspen trees served as the ceremony marker, while logs and lanterns lined the aisle.

Ashley's sister Courtney officiated the ceremony. "She's a beautiful writer, and she's been my rock," says the bride, who wore a wedding dress by Tara LaTour, with dotted point-d'espirit lace that reminded her of snow, and a Dennis Basso white fur cape. The groom donned a jacket by Samuelsohn and pants by Ermenegildo Zegna.

Lane Compton (Hughes's best friend and a groomsman), Lyndsay Caleo (Ashley's sister and bridesmaid), Thomas O'Winter (Hughes's brother and best man), and Maddy August (Ashley's best friend and maid-of-honor) struck a pose on the way to the reception. 

The escort card table featured branches hung with golden monogrammed compasses—small circular pieces of paper inserted into compass lids directed guests to their seats.

"We love our nieces and nephews, and they were all in the ceremony," says Ashley. "After everyone walked down the aisle, I wanted them to have a fun, cozy place to go, so we set up a teepee with big shearling pillows and toys on the floor." The couple also arranged an accessories table for the kids to pick pieces like necklaces, crowns, and scarves from beforehand. ("One of my nieces was way overaccessorized. It was an adorable free-for-all," says Ashley.) The kids also enjoyeda special dinner of teriyaki grilled chicken, edamame, and rice.

An inviting play area stocked with toys was set up for the couple's nieces and nephews.

One niece snapped a pic with an Instax camera. The cameras were set out on the guest-book table so friends and family could leave photos alongside their well-wishes.

In lieu of a traditional guest book guests filled out cards with their advice, memories, and recommendations for date nights and trips.

Guests enjoyed cocktail hour on the museum's rooftop before moving indoors for a three-course dinner.

During the reception, guests dined at tables named for characters from the couple's favorite book, The Little Prince. The fun-loving pair adore the story, says Ashley, "because it reminds us to live a little bigger, love a little better, and never grow up."

Tables were set with lush garlands of heather, eucalyptus, eryngium, magnolia, salal, and grevillea.

Arrangements created from the same flora as the table garlands (with the addition of Italian ruscus) were suspended above the reception tables.

For the after-party, the group moved to Chefs Club at the St. Regis Aspen Resort, where guests played vintage games like Pac-Man and Skee-Ballin an arcade tent, took turns in the photo booth, and danced until 2 a.m. The couple took a horse-drawn "getaway carriage" from the reception to the after-party.

Ashley changed into her grandmother's circa-1947 wedding dress for dancing. The newlyweds chose Jay Z's "99 Problems" for their first dance song—but Hugo's folksy version instead of the original. "We wanted something fun to let loose to," Hughes says. "The band nailed it."

The three-tiered vanilla-bean cake featured lemon and coconut, and was decorated with olive leaves and seeded eucalyptus.

Ceremony and dinner location, Aspen Art Museum

Party location and wedding cake, Chefs Club

Event design, Ashley Sands O'Winter

Event planning, Bella Event Design & Planning

Event décor, rentals, and lighting, Pink Monkey Solutions

Catering, Epicure

Flowers, Aspen Branch Studio

Photography, Lacie Hansen

Cinematography, Aflātis Films

Stationery, Wouldn't It Be Lovely

Music, Daniel and Jake Sproul of Rose Hill Drive; Northstar

Rentals, Borrowed Blu

Tent, heaters, and stage, Premier Party Rental

Bride's gown, Tara LaTour

Accessories, Jennifer Behr crown; Ippolita earrings; Dennis Basso cape; Mann's Jewelers bracelets; Caleo Jewelry engagement ring; Beverley K diamond wedding band; Valentino shoes

Hair, Hair Artistry by Hilary

Makeup, Divine Beauty Artists

Kids' attire, J.Crew; Mischka Aoki

Groom's attire, Brunello Cucinelli overcoat; Samuelsohn jacket; Ermenegildo Zegna pants; W. B. Thamm tie; Eton shirt; Magnanni shoes

Horse and carriage, Aspen Carriage and Sleigh

Transportation, Corporate Transportation Specialists

Arcade, Mile High Arcade

Photo booth, Chipper Booth

Rehearsal-dinner location, Pine Creek Cookhouse