We all know how every season seems to have its unique blend of songs – even if not everyone is listening to literally the same playlist, at least the vibe of the songs tends to be pretty similar, to say the least. For the cold season, the main two tendencies are to listen to either carols (but those are concentrated more around the Christmas holidays themselves), or to Frank Sinatra songs. Indeed, few things are able to take the gloom out of cold and dark weather as well as these songs can: perhaps we just need to hear someone paint the gloom in a magical color in order to be able to believe it ourselves. Otherwise, we would be cranky about the weather non-stop, probably. And Frank Sinatra songs have become a de facto soundtrack for the whole season, holidays included but not limited to them. If you agree and if you’re not bored out of your mind with these evergreens yet, here is our list of 10 great Frank Sinatra songs for the upcoming winter season.

Frank Sinatra
Frank Sinatra

1. Fly Me to the Moon

Whatever you do, make sure the right person is around when this song plays at your pre-holiday get togethers, because nothing screams romance as much as “Fly Me to the Moon”. Also known as “In other words”, it has become the jazzy atmosphere standard, associated with Apollo missions to the Moon as well as with indoor winter romance.

2. The Way you Look Tonight

Another romantic choice from our list of the best Frank Sinatra songs to play this season, “The Way You Look Tonight” was initially sung by Fred Astaire, but is now more associated with Sinatra’s version.

3. I’ve Got You under my Skin

This song has a rich history which may be more than meets the eye, or in this case, the ear. It was composed by Cole Porter in 1936, brought to perfection on the back of a series of musical climaxes performed by an arrangement of Nelson Riddle (who took his inspiration from Ravel’s Bolero), and only then it was covered by Sinatra, who put his unique stamp on it and turned it into the song we love today. It is now one of the best known and most popular Frank Sinatra songs for winter and beyond.

4. Come Fly with Me

Although this song doesn’t talk about winter and snow and Christmas things, we think that it’s perfect for the winter precisely because it describes adventures and travel into remote warm and tropical places. It’s one of the few things that can make you forget about the cold on days when you feel like you can’t stand it anymore.

5. New York, New York

This is one of the sparkly Frank Sinatra songs from the more glamorous side of his music, while it talks of the city that never sleeps in enthusiastic terms, of chances to take and of hopefully lucky outcomes. This is why most of us have come to associate it with the wonderful giddy feeling of shopping for winter gifts.

6. Strangers in the Night

This is the best thing to dance with someone to if you want to romance them beyond any hope. The effect is increased if said dance happens to take place in a mistletoe-adorned room. All joking aside now, even though slow dancing isn’t necessarily a popular activity at parties nowadays, people can get more traditional and Christmas get-togethers, and this is one of the most romantic songs that are played at such meetings.

7. The Best is Yet to Come

Another hopelessly optimistic song from the legendary singer, “The Best is Yet to Come” was the last song which he ever sang in public, and its title is also engraved on his tombstone. If he could face the end with such optimism, then it’s a wonderfully hopeful message to carry around during the holiday season as well.

8. Something Stupid

One of the best known and most covered Frank Sinatra songs about love, “Something stupid” is a touching duet with Nancy Sinatra and its lyrics talk about the special kind of awkwardness between the lovers in the first stages of their relationship. It’s one of Frank Sinatra’s greatest hits and it can help any home feel cozier during the cold season. As a side note, this song is also quite popular at summer weddings, as well as a source of slightly corny quotes.

9. Santa Claus is coming to town

With this, we’re breaking into actual carols, fit for the holiday season and limited to only that time. You may be quite sick of this song already and resent the way it plays in every shopping mall or on almost every radio station in December. But the truth is that Christmas wouldn’t be the same without Frank’s deep voice and cheerful announcement of Santa’s approach.

10. Have yourself a Merry Little Christmas

Finally, this is one of the Frank Sinatra songs most associated with Christmas and holiday cheer, and with being tucked comfortably inside a warm place, with a hot drink, while the weather outside is frightful. Ok, ok, we know that’s actually a lyric from another popular Christmas tune, but we think the spirit is very similar. We hope you enjoyed our selection and that you’ll enjoy the upcoming winter season no matter the soundtrack!