Buddy Holly

"Holley started making demo recordings in 1954 with friends including Sonny Curtis, Larry Welborn and future Crickets drummer Jerry Allison. A pivotal moment came on Feb. 13, 1955, when Buddy and Bob opened for Elvis Presley at the Fair Park Coliseum in Lubbock. Another pivotal moment came a couple months later, on April 23, 1955, when Holley walked into Adair Music in Lubbock and traded his first electric guitar to salesman Clyde Hankins for a brand-new Fender Stratocaster (priced at $305)."

via Fender

In the photo: Buddy Holly using the guitar with his band "The Crickets".

The first documented electric guitar Buddy Holly owned was a Gibson Les Paul with a gold top. Though Buddy might have had a more inexpensive model electric guitar prior to the Les Paul, Buddy probably used this guitar when he and Bob Montgomery were performing on the radio and around Lubbock in order to give them a more electric country sound, not to mention to compliment the R&B numbers they were throwing into their set by 1955.

However, Holly did not like sound of Les Paul Goldtop; he also struggled with intonation issues. He swapped the Les Paul Goldtop in 1955 for a famous 1954 Stratocaster. The guitar was later bought by Sam Logan, who sold it to Buddy Holly Educational Foundation. It is now a part of exhibition of Buddy Holly Center in Lubbock, TX, according to 2017 Fretboard Journal magazine.

This photo shows Buddy Holly with a Gibson SJ 200 Acoustic Guitar.

Probably the most popular acoustic guitar that Buddy owned was the Gibson J-45 that he hand-crafted his own leather cover for as decoration. This cover included his name on the face, the songs on from his first Decca single-- "Blue Days, Black Nights" and "Love Me" on opposing sides of the top of the body by the neck, as well as having TEXAS spelled out along the bottom portion of the guitar in white lettering.

Holly's J-45 was extensively covered in a 2011 Guitar World article.

Buddy Holly is seen using what appears to be Elvis Presley's alternate Martin D-28 guitar in a rehearsal photo, alongside his Fender Stratocaster, Bill Black's bass, and DJ Fontana's drums, as documented by Scottymoore.

According to Scottymoore, Buddy Holly used a Martin D-18, though there is some speculation it might have been a Martin D-28 instead.

Buddy Holly used the Harmony Stratotone during his early years. This is evidenced by a photo available through Google Images. It is unclear if he used this guitar in any recordings.