Gifts for Guys: The 12 Days of Menswear

Each week, guest blogger Jeremiah Simmons of A Headlong Dive shares men's style tips.

Each week, guest blogger Jeremiah Simmons of A Headlong Dive shares men's style tips.

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On the first day of Christmas, my true love sent to me . . . the Perfect Navy Blazer by Isaia:

Forget about the partridge in a pear tree. If your true love is sending you something, it should be this Isaia jacket. While you probably already own a navy blazer, trust me that unless you own one with the construction, silhouette, shape, and signature Mediterranean red-coral lapel pin, you are missing out. (Isaia Aqua Lite Navy Two-Button Blazer, $1,677; parkandbond.com)

On the second day of Christmas, my true love sent to me . . . Two Pairs of Wear-Everywhere Suede Shoes:

Give your longwings a break and stand out from the crowd in suede. The snuff and sand colorations will look even better after a little attrition, and the double-monk-strap and chukka varieties will literally work with everything you own. (Ovadia & Sons Snuff Suede Milford Double Buckle Shoes, $595, ovadiaandsons.com; Alden Sand Suede Flex-Welt Chukka Boots, $420; epauletshop.com)

On the third day of Christmas, my true love sent to me . . . Three Pairs of Levi's Vintage Jeans:

This is the only denim you'll ever need, in the only three washes you'll ever need—Rigid, One Love, and Rodeo Hero. The slim, straight leg will keep these 1947s a relevant part of your wardrobe until 2047, while the 14-ounce shrink-to-fit selvage denim (woven at the historic Cone Mills White Oak Plant in Greensboro, North Carolina) ensures they age perfectly. (Levi's Vintage Clothing 1947 501 Jeans, $235-$265 each; unionmadegoods.com)

On the fourth day of Christmas, my true love sent to me . . . Four Leather Accessories from Makr:

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Your accessories say more than you think they do. Don't be that guy who neglects his everyday carry and whips out a Velcro wallet—get your hands on some adult accessories (belt, wallet, key chain, and sunglasses case) from Makr Carry Goods. (Makr Carry Goods accessories, $32-$120; makr.com)

On the fifth day of Christmas, my true love sent to me . . . Five Pairs of Unis Chinos:

I usually avoid anything with the word skinny in the title like the plague, but don't let the moniker fool you. Unis constructs Gio like tailored trousers, with the button fly and the full-waist curtain. They will instantly become your new favorite pants. (Unis Gio Skinny, from $139; unisnewyork.com)

On the sixth day of Christmas, my true love sent to me . . . Six Filson Bags:

Filson has been making durable goods with stunning aesthetics longer than any of us have been walking this world. A set of its bags will have you covered whether you have a business trip to New York or are going fly-fishing in Montana. (Filson bags, from $35-$795; filson.com)

On the seventh day of Christmas, my true love sent to me . . . Seven Sid Mashburn Cashmere V-Necks:

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I have only two rules when it comes to sweaters: Always go V-neck, and always go cashmere. With sweaters that look this good, choose whatever the hell six colors you want, but if I were you, I'd go Nantucket red, aqua green, deep purple, blue heather, navy, green heather, and gray. (Sid Mashburn cashmere V-neck sweaters, $275 each; sidmashburn.com)

On the eighth day of Christmas, my true love sent to me . . . Eight Handmade Drake's Ties:

The tie is the one place where a man gets to express himself loud and proud. It is the one part of a man's attire that doesn't meet a functional need but is there strictly for decoration, so be self-indulgent and invest in outstanding details and superb quality. Handmade in England, these ties are unmatched in the wide world of menswear. (Drake's ties, $135 and up; barneys.com)

On the ninth day of Christmas, my true love sent to me . . . Nine Button-Up Shirts by Taylor Stitch:

Taylor Stitch has changed how I look at shirting. They're sized by chest (like suiting), which creates a more custom fit. Plus, all of the shirts are cut with a higher armhole, and each shirt also has a three-inch taper through the body, producing a slim fit without being overly taut. (Taylor Stitch shirts, $125 each; taylorstitch.com)

On the tenth day of Christmas, my true love sent to me . . . Ten Pairs of Knot Cuff Links From Brooks Brothers:

Unless you are truly going formal, avoid the often-ostentatious sterling-silver varieties and throw the knotted version in your French cuffs. And for God's sake, avoid any cuff links with trains, planes, or automobiles on them, unless you are under the age of 12. (Brooks Brothers Knot cuff links, $9; brooksbrothers.com)

On the eleventh day of Christmas, my true love sent to me . . . Oak Street Bootmakers Aromatic Cedar Shoe Trees:

Every single pair of leather shoes you own should have its very own pair of cedar shoe trees. Cedar will preserve your precious footwear investments and absorb moisture, a.k.a. your sweat. (Oak Street shoe tree, $30; oakstreetbootmakers.com)

On the twelfth day of Christmas, my true love sent to me . . . a Case of Gentleman Jack:

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Christmas crowds, office parties, family gatherings—who doesn't need a drink during the holidays? Maybe it's the Tennessean in me or the charcoal mellowing process, but I opt for the Gentleman during cocktail hour. A case under the tree will go a long way into the New Year.

For more of Jeremiah's menswear finds, head over to his blog, A Headlong Dive.

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