Vocalist James Graham commented on the difference between the band's live show and the album, stating that, "If you came to see us live before you actually heard the record or any recordings we made, you'd probably think we were kind of a noisy band. If you had the record and sat down with it, you can totally see it's more than noise."
The Twilight Sad performed Fourteen Autumns & Fifteen Winters in its entirety for the first time in December 2013, with further UK dates performing the full album in April and May 2014. The tour dates coincided with the release of a deluxe edition reissue of the album, with bonus tracks including demos and rarities, released on Record Store Day 2014. The reissue was pressed as a double vinyl LP, limited to 500 copies only, and available in the United Kingdom only.
Regarding the album's lyrical content, James Graham remarked that "All the songs are just pretty much about what's happened to us, people that I know, and where we live. [...] I never really tell anyone what the songs are about because my favorite songs are the ones that I don't really know the exact meanings to either; I have my own perceptions of those songs and can relate it back to myself. So, it's just something that I always said, that I would keep what the songs are all about to myself." In a 2014 track-by-track interview about the album with Drowned in Sound, Graham remarked that opening track "Cold Days from the Birdhouse" was one of the last songs written for the album, but was originally set to be a B-side, which he claimed is "a terrifying thought as 'Cold Days' is one of the most popular songs and has been the song that's introduced so many people to our music." First single "That Summer, at Home I Had Become the Invisible Boy", whose title is a reference to the film Stand by Me, was the first song the band had ever written, and was inspired by "some pretty bad things" that happened to the band members and people close to them. The song has also been one of the band's most enduring songs, having been played at every live performance since it was written. The accordion featured in many of the songs on the album, including "Walking for Two Hours" and "I'm Taking the Train Home", was found by guitarist Andy MacFarlane in the attic of his house. Graham stated in 2014 that the accordion is "unfortunately now broken." "Last Year's Rain Didn't Fall Quite So Hard" was inspired by Animal Collective's 2004 album Sung Tongs, with MacFarlane and Graham creating melodies and vocals to loop, a writing and recording method the band had never tried before. "Talking with Fireworks / Here, It Never Snowed" is referred to the band as "Loud/Quiet" on their setlists; and when performed live, Graham provides extra cymbal crashes, sometimes even playing the cymbal with his head.
Graham has said that centerpiece "Mapped by What Surrounded Them" is a tough song to sing live given the subject matter, and the song's title is a reference to the book and film The Virgin Suicides. Online independent music site GoldFlakePaint analyzed the song as swiftly turning "childish imagery ('She's sitting in the primrose garden and she's playing with her toys') into something far more darker [sic] ('...and she's taken far too young') without ever explicating the full story; though talk of 'walls filled with blame' and visions of the protagonist watching 'Emily dance' in his dreams, only leads us to the most awful of assumptions." Second single "And She Would Darken the Memory" was the band's first song with an accompanying music video, directed by Mark Charlton. Closing instrumental "Fourteen Autumns and Fifteen Winters" was inspired by Serge Gainsbourg and the chord changes he would use; according to MacFarlane, "It had a big influence on the music, particularly this song. I've never had a piano or been able to play it, which is why it sounds like a drunken, out of time mess." A special CD edition of the album was released in late 2007 with the bonus track "Watching That Chair Painted Yellow", which was the B-side to "That Summer, at Home I Had Become the Invisible Boy".
The album's artwork was created by graphic designer/illustrator Dave Thomas, a.k.a. DLT, who has created and designed artwork for all of The Twilight Sad's releases to date, as well as for several other Fat Cat Records releases, among many others. The 'boy in the mask' on the album cover and inside booklet illustrations graced the covers of the album's subsequent singles: the 'boy and girl' image was featured on the cover for "That Summer, at Home I Had Become the Invisible Boy"; the 'boy falling back in the chair' image was featured on the cover for "And She Would Darken the Memory"; and the image of the 'boy about to smother his mother with a pillow' was used for the album's companion release Here, It Never Snowed. Afterwards It Did in June 2008. A similar illustration featuring the boy and the girl had previously appeared on the cover of the band's self-titled debut EP in 2006. Additionally, in December 2013, when the band performed Fourteen Autumns & Fifteen Winters live in its entirety at King Tut's Wah Wah Hut in Glasgow, handmade fabric replica masks were produced in limited quantities and sold to concert-goers. Limited edition screen prints featuring the album's artwork were also produced to coincide with the live shows.
Fourteen Autumns & Fifteen Winters was released to positive reviews. At Metacritic, which assigns a normalized rating out of 100 based on reviews from mainstream critics, the album has received a favourable score of 79, based on 16 reviews.Pitchfork Media reviewer Mark Richardson praised the "vividness of the lyrical themes" and "street-level earthiness", awarding the album an 8.6 out of 10 rating and branding it with their Best New Music tag. Richardson concluded that "The Twilight Sad approach the darker side of growing up with consideration and dignity, and manage to maintain a proper perspective. "As my bones grew, they did hurt / They hurt really bad," an angst-filled songwriter from another generation once sang; the Twilight Sad do a tremendous job of remembering that ache."The Skinny awarded the album 5 out of 5 stars, hailing the album as "one of the finest Scottish albums in years." Both The Skinny and Teletext's music page Planet Sound named Fourteen Autumns & Fifteen Winters as the best album of 2007. Regarding the album's warm critical reception, guitarist Andy MacFarlane stated that the band didn't expect the acclaim and that they "just wanted to release something that we were happy with," adding that "[the band] didn't expect anyone else to like it."
In December 2007, the album's opening track "Cold Days from the Birdhouse" was voted number 73 on Pitchfork Media's "Top 100 Tracks of 2007" list. In December 2009, Fourteen Autumns & Fifteen Winters ranked number 2 in The Skinny's "Scottish Albums of the Decade" list.
A 2012 review by UK site GoldFlakePaint praised the album, stating "Six years [sic] on from its release, Fourteen Autumns and Fifteen Winters is as compelling and striking as it ever was. It's a record that offers poetic and macabre sketches of desolate landscapes, and the disorientating and isolated anthropological existences that pass through them. We catch occasional small glances into the heart of them, but we never see enough of the spectacle to create full portraits; and it's those abstruse yet alluring oddities that makes the record so resoundedly intriguing to this day. A demanding but profoundly moving masterpiece."