Skip to Main Content

A Swingin’ Thanksgiving Playlist

November 22nd, 2023

25 Choice Cuts For A Stylish Holiday

Ah, I can smell it already. Can you? The turkey’s just been pulled out of the oven and its perfectly roasted scent mingles with the stuffing, sweet potatoes, pumpkin pie, and the faint smell of wood burning in the living room fireplace. The television’s on in the background — possibly the Macy’s Parade, National Dog Show, or football game — though nobody’s really paying attention. Guests are seated throughout, nibbling on crackers, cheese, and pepperoni. You’re holding a perfectly made Old Fashioned in your hand.

The only thing this Thanksgiving tableau is missing is a great playlist to help set the mood.

Although Thanksgiving is typically regarded as the unofficial kickoff to the Christmas season — never mind that you start seeing Christmas decorations in stores before Halloween these days — one thing that I’m pretty firm on is that Christmas music can be played after Thanksgiving, not before. So I’ve put together a curated list of 25 swinging jazz tunes that could vaguely be termed “Thanksgiving music.”

Enjoy and Happy Thanksgiving, all!

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

All Posts

Edited by Rachel Butler


Another week, another great drop here in the HSS Shop. Today, I’m pleased to introduce our brown double-breasted flannel suit. It’s a bit perplexing that it’s taken us this long to add this particular suit to the collection given my penchant for brown clothing of any kind, but better late than never, as they say. In this post, we’ll discuss some of the benefits of a brown suit, why you should consider a double-breasted suit, as well as the garment and outfit styling.

Let’s dig in.