Ivy Style Holiday Gift Guide for Men 2025

By Matthew Longcore

Christmas is merely three weeks away, so it is time to be making your shopping list and checking it twice. While gift giving is always a matter of taste – for both the giver and the receiver – the process of narrowing down items is less daunting with some good advice. Here is a carefully curated list of gift suggestions for the Ivy Style afficionado.

Wishing a happy holiday season to all!

Polo Ralph Lauren

Classic Fit Plaid Oxford Shirt

According to Polo RL, the fabric of this iconic shirt has “a secret wash that gives it instant character, ease, and a heathered softness” – a formula which has endured for more than three decades.

The tartan pattern in green, navy, red, and gold is perfect for the holiday season and beyond.

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Brooks Brothers

Merino Wool Archive Plaid Intarsia Sweater

This beautiful tartan sweater in green, red, blue, and white is knit in 100% wool.

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Signature Tartan Stick Umbrella

Rainy days can be stylish, too. Form meets function in this large umbrella featuring the signature BB#1 tartan print.

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Smathers & Branson

Stainless Steel Needlepoint Flask

Equestrian elegance is epitomized by the time honored tradition of fox hunting. This needlepoint design from Brooks Brothers + Smathers & Branson looks sharp on a stainless steel flask, perfect for gatherings at the hunt club or tailgating during football season.

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The Andover Shop

Christmas Tartan Bow Tie

Every man should have a tartan bow tie for the holiday season. This one comes in two timeless classics, Black Watch or Prince of Wales.

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Christmas Stag Mid-Calf Dress Sock

Another must-have for wintertime. The stag and snowflake pattern is truly iconic. It looks as good on socks as it does on sweaters.

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Woven Navy and Green Tartan Wool Scarf

Navy, green, red, and gold make for a handsome color combination This tartan wool scarf will keep you warm and stylish.

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J. Press 

Made-in-England Plaid Cashmere Muffler

There is nothing quite like the softness of cashmere. This muffler in a Tattersall pattern exemplifies Anglophile style.

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Made-in-USA Striped Grosgrain Ribbon Belt

Belts can be bulky, but not this one. Grosgrain ribbon is lightweight and comfortable. This belt is available in several color combinations. Perhaps even those of your beloved alma mater.

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Splash of Pink 

Men’s Stuff Tie And Pocket Square

If you have the opportunity to visit somewhere warm this winter, you’ll want to dress accordingly. Lilly Pulitzer has reintroduced neckties and pocket squares for men who appreciate tropical prints.

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American Trench 

The Shetland Tweed Blazer

American Trench is a Made in the USA brand with an emphasis on quality and attention to detail. Their Shetland Tweed Blazer is an instant Ivy classic featuring a 3-roll-2 button configuration, natural shoulders, and a single back vent.

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Timeless Tartans 

Collegiate Tartan Pocket Square

The patented algorithm from Timeless Tartans combines the founding year, campus coordinates, and official colors of colleges and universities to create a unique pattern. Check out the list of affiliated institutions.

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Duck Head 

1865 Intarsia Sweater

This sweater is clearly inspired by the collegiate class year sweaters featured in Take Ivy. This version showcases 1865 – the founding year of Duck Head, a legacy brand celebrating its 160th anniversary.

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Jay Butler

Cromwell Penny Loafer

This penny loafer from Jay Butler epitomizes Ivy League style. The black and brown leather versions are as classic as it gets. The dark brown and navy blue suede version are especially elegant.

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St Johns

Travel Size Madras Dopp Kit with Mini Spray

This smart looking sundry bag comes complete with Madras mini spray cologne, hair wash, hair cream, body lotion, and body wash. The perfect gift for the business traveler or vacationer.

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Sebago x St Johns Bay Rum Canvas Dopp Kit

This collaboration between two heritage brands results in a nautical and stylish dopp kit in natural and navy canvas.

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Caswell-Massey 

Newport Cologne

Newport, Rhode Island is known as the “City by the sea.” This cologne, which takes its names from Caswell-Massey’s historical roots in Newport, evokes the freshness of a summer day in the seaside resort.

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Mercer & Sons 

British Country Brushed Cotton Flannel Tattersall Shirt

Northing evokes the English countryside quite like Tattersall. This soft cotton flannel shirt has British sensibilities and is proudly made in the USA.

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Chipp Neckwear 

English Bulldog Tie

Dogs are the Ivy Style man’s best friend. Whether we are talking about mascots, pets, or fur babies, dogs are worthy of celebration. Chipp Neckwear makes beautiful neckties featuring many favorite breeds, including this one showcasing the beloved English bulldog.

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Fish Creek

Custom Needlepoint Flask

Fish Creek makes 100% hand-stitched needlepoint flask featuring personalization with monograms in traditional block letters or signal flags. If you have a sailor or boater in your life, the nautical option is the way to go.

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Books

Take Ivy by Shosuke Ishizu

Originally published in Japan in 1965, this book is a must-have for all readers of Ivy Style. Perhaps no book has been more influential in photographing and celebrating the Ivy League look.

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Preppy Style: A Modern Guide to Timeless Fashion by Rosalyn Gomersall

This year marks the 45th anniversary of The Official Preppy Handbook, which was first published in 1980. The recently published book titled Preppy Style iis a testament to the enduring popularity of the preppy look, from its inception as the fashion of Ivy League students to its contemporary interpretations.

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The Pennant by Richard English

Richard English has collected vintage wool-felt pennants for over 30 years. This book is a tribute to the bygone era of pennants and banners—all antique, all wool, and all with sewn letters and designs.

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Ralph Lauren: In His Own Fashion by Alan Flusser

Alan Flusser is the author of Dressing the Man, the seminal tome on men’s fashion. This coffee table book features the life and work of Ralph Lauren, the keeper of the torch for Ivy League style.

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11 Comments on "Ivy Style Holiday Gift Guide for Men 2025"

  1. What, pray tell, is a tweed blazer?

    • Matthew Longcore | December 4, 2025 at 4:59 pm |

      I believe you are referring to the name of the product which comes directly from the maker, American Trench. While it is perfectly reasonable to question nomenclature, it seems a bit nitpicky in this particular case. This item, which is made in America, exemplifies the Ivy League look in every detail – from the natural shoulders silhouette to the 3-roll-2 button configuration.

      • Yes. It is a lovely piece. I just hope that whoever writes the copy learns that a blazer is a specific (-ish) type of odd jacket, and a tweed jacket is another. Even the traditional clothing devotee who does not lean ivy knows and respects these distinctions.

        • I agree with you, but the term “blazer” has been used for decades to refer to any “odd jacket”. Many people even call sport coats and blazers “a suit”, which is of course nonsensical.
          What annoys me much more is when a white tie and tails ensemble is referred to as a “tux”. The tuxedo (dinner jacket) was invented specifically to be different from white tie and tails!

  2. All terrific suggestions. I’d also add Royall fragrances to the list of gift ideas.

    Kind Saturday Afternoon Regards,

    H-U

  3. The people who for decades used blazer to refer to any old odd jacket were WRONG and knew nothing about men’s clothing.

  4. No, everything is not a blazer. I’m not saying it has never happened, but I’ve never even heard of this until the new hires came along in the recovery following Covid. Never before at Ivy-style.com and I’ve been around “awhile”. I certainly have never heard my dad refer to a sport-coat as a blazer. Same with “suit”. This is what happens when fathers don’t raise their sons.

    “Odd-jacket” is English. “Sport coat” and “sports jacket” are both “American English”. (Pretty sure.)

    I’m not sure, but “Sports jacket” may be west coast English, used once by Charlie speaking to Alan on Two and a Half Men.

    Addressed in the comments 10 Sep, 24 here:

    https://www.ivy-style.com/the-return-of-the-j-crew-catalog.html

  5. If American Trench succeeds we all win. The All-American business model is the ideal. That will pressure others to up their game. Did I see a cardigan in there somewhere? If you live near Philly and you need a jacket, go get one if it fits.

  6. As for BB umbrellas, I bought one 2019 or 2020. Classic black with Bamboo cane handle. Unfortunately, somebody took mine last winter. If BB still sold one like that, for a reasonable price I would buy it.

    • Once upon a time I had a wonderful solid wooden shaft umbrella I got at Brooks in 1977. Years later, here in Austin, it disappeared in a local auto dealership. I replaced it with another solid wooden shaft umbrella, this one from Kent Wang. It is not a Brigg or a Fox, but it is quite nice and much less expensive.

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