About The Song
“Try Not to Look So Pretty” is a country single co-written and recorded by American artist Dwight Yoakam. The song appears on his fifth studio album, This Time, released by Reprise Records on March 23, 1993. It was issued as the album’s fourth single on February 14, 1994, with “Wild Ride” as the B-side. The track was recorded in 1993 and runs approximately 2 minutes and 52 seconds. On the charts, it reached No. 14 on the Billboard Hot Country Singles & Tracks chart in the United States and climbed to No. 4 on the RPM Country Tracks chart in Canada.
The parent album This Time is widely regarded as Yoakam’s most commercially successful release. Recorded at Capitol Studios in Hollywood and produced by longtime collaborator Pete Anderson, the album combines country and honky-tonk foundations with broader influences from rock and soul. It peaked at No. 4 on the Billboard Top Country Albums chart and later achieved triple-platinum certification from the Recording Industry Association of America (RIAA). Within this context, “Try Not to Look So Pretty” forms part of a strong sequence of singles that also includes “Ain’t That Lonely Yet,” “A Thousand Miles from Nowhere,” “Fast as You,” and “Pocket of a Clown.”
Songwriting credits for “Try Not to Look So Pretty” go to Dwight Yoakam and Kostas (Kostas Lazarides), a Greek-born country songwriter who collaborated frequently with Yoakam in the early 1990s. The track continues the pattern of Yoakam–Kostas co-writes that appears across several albums, and it fits into a broader body of Kostas’s work for prominent country artists of the era. Production is handled by Pete Anderson, who oversaw most of Yoakam’s classic-period recordings and helped define the blend of Bakersfield-influenced guitar work and contemporary studio polish associated with Yoakam’s sound.
Lyrically, “Try Not to Look So Pretty” deals with the difficulty of maintaining emotional distance from someone who still has a strong hold on the narrator. The refrain centers on a request that the other person “try not to look so pretty” so that he will not fall back into the same patterns or feel like a fool. Verses describe how her presence disrupts his resolve and how physical attraction complicates any attempt at moving on. The language is direct and conversational, in line with honky-tonk storytelling traditions, but framed in the concise, radio-friendly structure typical of early 1990s country singles.
Musically, the song fits the broader approach of This Time, where Yoakam and Anderson expand beyond straight honky-tonk while keeping core country elements intact. The arrangement features a steady mid-tempo groove, electric and steel guitars, and a rhythm section that supports Yoakam’s characteristic twangy tenor. Subtle touches drawn from rock and roots music appear in the guitar tones and overall production, but the track remains clearly within a country framework. This balance between traditional instrumentation and a slightly more modern sound mirrors the album’s general strategy.
As a single, “Try Not to Look So Pretty” did not reach the same chart heights as the album’s earlier releases, which had all peaked at No. 2 on the U.S. country chart. Nonetheless, a Top 20 showing on Billboard and a Top 5 peak in Canada confirmed its status as a solid hit within Yoakam’s catalog. A music video directed by Gregory R. Alosio, with Yoakam’s involvement, supported the single’s promotion and received airplay on country music television outlets. The song also appeared on year-end country charts in Canada, reflecting its sustained rotation there through 1994.
Over time, “Try Not to Look So Pretty” has come to be viewed as a representative example of Yoakam’s early-1990s work: a concise, hook-driven country song grounded in classic themes but delivered with a slightly updated sound. The track regularly appears in discographies documenting Yoakam’s collaboration with Kostas and in overviews of This Time, where it is noted as one of the five singles that contributed to the album’s commercial and critical success. Its combination of straightforward lyrics, distinctive vocal style, and carefully crafted production illustrates the qualities that defined Yoakam’s mainstream peak.
Video
Lyric
Try not to look so pretty
The next time that we meet
Please don’t look so pretty
And I won’t act so weak
Please don’t look so pretty
You’re lovely but it’s just cruel
Try not to look so pretty
And I’ll try not to be your fool
You walk in and steal my mind
But who gave you the right
To treat me like some useless thought
You know away each night
Please don’t look so pretty
You’re lovely but it’s just cruel
Try not to look so pretty
And I’ll try not to be your fool
You make it hard on me
But I’ll try to pretend
That you’re just a lovesick dream
That always has to end
Please don’t look so pretty
You’re lovely but it’s just cruel
Try not to look so pretty
And I’ll try not to be your fool