Silvia Bolognesi was born August 5, 1974, in Siena. She trained classically first, earning a double bass diploma from the Giuseppe Verdi music institute in Prato and the R. Franci Institute in Siena under Maestro Andrea Granai, with further study under Maestro Alberto Bocini, before moving into jazz through the Accademia Siena Jazz under Paolino Dalla Porta, Furio Di Castri and Ferruccio Spinetti. Her own account of her development also names a string of American avant-garde figures she studied or worked directly with during this period and after: William Parker, Muhal Richard Abrams, Lawrence "Butch" Morris, Roscoe Mitchell and Anthony Braxton.

She made her leader debut with Introducing Open Combo (33 Records, 2005), recorded with her sextet at the Siena Jazz Association in October 2004, and followed it with a second Open Combo album, What Was I Saying? (33 Records, 2008). In 2010 Musica Jazz magazine's critics poll named her the year's Top Jazz new talent, and she also won the 2010 InSound trophy for double bass; in 2020 her band Young Shouts won "Jazz New Generation," and their 2019 album aLive Shouts was Bandcamp's "best record of the month" that August. She founded her own label, Fonterossa Records, in 2010, and has directed the Fonterossa Open Orchestra, based at the PisaJazz festival, since 2017, where she has also served as the festival's "Fonterossa Day" artistic director since 2015.

Her discography after the Open Combo records moves increasingly toward duos and small collaborative groups: Holidays in Siena (Rudi Records, 2011), a duo with American reedman Sabir Mateen; Hear in Now (Rudi Records, 2012), a co-led trio with violinist Mazz Swift and cellist Tomeka Reid that toured the American Midwest and New Orleans that year and released a second album, Not Living in Fear (International Anthem, 2017); Suoni dal Carcere (Rudi Records, 2013), a duo with vocalist Maria Pia De Vito; and Dialogo (Terre Sommerse, 2013), a duo with trumpeter Angelo Olivieri. Chicago Sessions (Fonterossa Records, 2015) reunited her with Tomeka Reid and added Chicago drummer Mike Reed, trumpeter Russ Johnson and vocalist Dee Alexander, documenting a period in which she returned repeatedly to Chicago to work with musicians connected to the AACM.

A long-running duo and trio partnership with Italian clarinetist Marco Colonna runs through much of the following decade: Ghost Trio (Setola di Maiale, 2015, with drummer Ivano Nardi), a live duo recording at Burgos's Espacio Tangente (2016), and the duo album EraorA (Fonterossa Records, 2021). The two also appear together as featured players in Slovenian drummer Zlatko Kaučič's quintet on Morning Patches (2019), alongside Michael Moore and Albert Cirera. In 2021 she formed the piano trio Cats in the Kitchen with pianist Alberto Braida and drummer Cristiano Calcagnile, releasing a self-titled album on We Insist! Records built around Braida's compositions. She also appears on trombonist Giancarlo Schiaffini's career-retrospective box set Schiaffini (Auditorium Edizioni, 2012), playing double bass on his composition "Con Spaventata Passione," and, the same year, on If Not (Omaggio a Mario Schiano) (Terre Sommerse, 2012), an ensemble recording of compositions by the late saxophonist Mario Schiano led by trumpeter Angelo Olivieri and reedman Alipio Carvalho Neto, on which Schiaffini and vocalist Maria Pia De Vito also appear; Schiano himself, who died in 2008, is credited only as a composer on that record, not a performer.

Since 2017 Bolognesi has been a regular member of the Art Ensemble of Chicago's expanded large ensemble under the group's surviving co-leaders Roscoe Mitchell and Famoudou Don Moye, recording We Are on the Edge: A 50th Anniversary Celebration (Pi Recordings, 2019) and The Sixth Decade: From Paris to Paris (RogueArt, recorded live at the Sons d'Hiver festival in 2020, released 2023), the latter also featuring Roscoe Mitchell, Tomeka Reid, Nicole Mitchell and Dudù Kouaté among its personnel. By her own account she has also been a member of the Roscoe Mitchell Quintet since 2022. Her more recent leader projects include Timing Birds (Astral Spirits, 2024), a trio with Senegalese percussionist Dudù Kouaté and engineer-musician Griffin Rodriguez; Is That Jazz? Celebrating Gil Scott-Heron Live (Fonterossa Records, 2024), a large ensemble she arranged and conducted with American vocalist Eric Mingus, son of bassist Charles Mingus; and Jungle Duke (Caligola, 2025), featuring Chicago alto saxophonist Nick Mazzarella and fellow Italian violinist Emanuele Parrini.

She currently teaches double bass and combo class at the Accademia Siena Jazz, having previously taught jazz double bass at the Conservatorio Statale di Palermo, and has led improvisation and conduction workshops with the PisaJazz festival since 2007; since 2016 she has also taught through the Erasmus+ exchange program in Maastricht, Tbilisi, Riga and Birmingham.

Bolognesi's catalogue sits almost entirely inside free jazz and European free improvisation, built from small, flexible groupings rather than a single standing working band: duos with a single reed, string or vocal partner (Sabir Mateen, Marco Colonna, Maria Pia De Vito, Angelo Olivieri) recur as often as any larger project, and even her bigger ensembles, Hear in Now, Cats in the Kitchen, the Zlatko Kaučič Quintet, are collaborative co-led groups rather than a repertory band under her own name alone. This mirrors the working method of several of her most direct influences and teachers, among them William Parker and Roscoe Mitchell, both figures associated with large-ensemble and small-group improvisation built on real-time interaction rather than fixed arrangement.

Her Chicago connections run deeper than any single record: repeated returns to the city beginning around 2012, documented across Hear in Now, Chicago Sessions and Not Living in Fear, put her in direct and repeated contact with AACM-associated musicians (Tomeka Reid, Mike Reed, Dee Alexander) and, from 2017 onward, with the Art Ensemble of Chicago's surviving leadership itself. That relationship, now spanning two Art Ensemble albums and, by her own account, a seat in Roscoe Mitchell's working quintet, places her among a small number of Italian musicians with a sustained, recorded connection to the AACM's original Chicago generation rather than a one-off guest credit.

Alongside her improvising work, Bolognesi has built an institutional footprint unusual among her generation of Italian jazz bassists: founding and running her own label (Fonterossa Records, since 2010), directing a standing large ensemble (the Fonterossa Open Orchestra, since 2017), and holding jazz double bass teaching posts at two separate institutions (Accademia Siena Jazz and, previously, the Conservatorio Statale di Palermo).