Dalbesio was crowned, in 2004, Miss Wisconsin Teen USA at the age of 16. Through the pageant she was scouted by Jeff and Mary Clarke who tried to put her in regular-size modeling.
After being turned away by "straight-size" model agents at a scouting event in St. Louis, Missouri, at age 16, Dalbesio was eventually signed by the Ford Modeling Agency as a plus-size model when she came in for a meeting at age 18.
Originally categorized as plus-size (size 10), label.
She has appeared in editorials for magazines including LOVE, Purple, Vogue India, Dazed & Confused, Lui, Bon, Oyster, Twin, Viva Moda, Elle France, and Elle Italia.
In December 2014, Dalbesio appeared on the cover of Lady magazine, shot by Daniel Arnold. In April 2015, she was featured on the cover of Tush Magazine, photographed by Armin Morbach, followed by covers for Glamour Iceland, Madame, Lifetsyle, Suited, Feeling, and P Magazine. The P Magazine cover was a self-portrait.
Dalbesio was selected for Calvin Klein's "Perfectly Fit" underwear campaign in 2014. Her designation as "plus-size" caused some controversy. In an interview with Elle magazine, Dalbesio said although she was larger than previous models used in Klein campaigns, she considers herself "in-between" rather than plus sized.
In 2015, Dalbesio was placed on Models.com's "Hot List", a ranked category for rising stars in the modeling world, and Maxim magazine's "Hot 100 for 2015".
Dalbesio has appeared in campaigns for H&M, Levis, Abercrombie & Fitch, and Coach. She was named the face and brand ambassador for Prima Donna Lingerie for years 2016 and 2017.
In 2016 Dalbesio photographed herself for a self-portrait story for the first non-nude issue of Playboy.
Dalbesio identifies as a "multi-disciplinary visual artist," and explains that her work "is greatly influenced by the examination of traditional and sexual femininity, mystical nature, and the place where the two meet."
In 2011, she had three performance art shows called Homecoming, Homecoming: Sophomore Year, and her Young Money exhibition. Her last performance art piece, titled Young Money, included dressing up like a stripper and covering herself in fake tanner and champagne at the Chelsea Art Walk. It was reviewed favorably by the New York Times.
She has exhibited her work internationally, and published two books. The first, Born Rich, was published by Edition Faust in 2013, and the second, Studies of Ecstasy, was published by Melville Brand Design in 2015.
In 2016 Dalbesio curated an all-female art show for the New York-based fair SPRING/BREAK. Titled You Can Call Me Baby, the show featured artists whose work "aimed to reclaim symbols traditionally used to undermine women". The show was lauded bycritics, including gaining a glowing review from notoriously difficult critic Paddy Johnson. In December, critic Jerry Saltz included the show in his list of the 10 Best Art Shows of 2016 for New York Magazine's Vulture.
Dalbesio's photographs have appeared in magazines such as Playboy, HEARTS, 2003, and P Magazine, appearing on the cover of both 2003 and P Magazine.
Dalbesio has written short essays for a number of publications including Suited, Twin Magazine and Oyster, and wrote a regular column for Elle.com called "Girl on Girl".
Dalbesio identifies as a feminist. In 2017 she launched Our Stories, Ourselves with curator Jayne Johnson. The site serves as a "non-partisan space for women to share their experiences" in video responses to weekly prompts.