Alessi starting writing and performing aged 16. She recorded her first album *'Notes from the Treehouse' *in Omaha, Nebraska with Bright Eyes producer and band member, Mike Mogis. The album was released through Virgin records in 2009 and Alessi toured extensively in the UK and Europe in support of the release with Mumford & Sons, Johnny Flynn and Laura Marling amongst others.

Alessi signed with Bella Union in 2009 and released* 'Soul Proprietor' *EP in 2009.

Alessi's second album *'Time Travel' *was released to great acclaim on Bella Union in 2011. Alessi toured the UK,EU and US with John Grant, Laura Marling, Laura Veirs and Villagers in support of the release.

Alessi's third album *'The Still Life' *was produced by Bright Eyes/Azure Ray collaborator, Andy LeMaster, in Athens, Georgia in 2013. The album was also released by Bella Union and Alessi toured extensively in support of the album with Mountain Goats, M.Ward, Jenny Lewis and Sam Amidon.

Alessi also released an EP titled 'Komorebi' in Japan in 2014 and has toured the country twice in support of her releases.

Alessi has also recorded vocals for Neva Dinova, Young Colossus, Valley Lodge, Cursive and Rachael Dadd amongst others.