On Jack III:

He’ll look sharp in these wardrobe staples—Bills Khakis collared shirt ($155), Bills Khakis sweater ($295), Bills Khakis pants ($165), all from Mister Guy.

Packing for the holidays has never been more simple and stylish with this Moore & Giles American Bison bag, $635, Mister Guy Clothiers.

Keep him warm—and cool—with these Dents gloves, $195, Mister Guy Clothiers.

On Sara:

Dress her to impress in this leather and lace BB Dakota Jack dress, $60, Marta's.

All eyes will be on her with this 7.43-carat tanzanite ring with .67 carats of white diamonds set in platinum, call for pricing, Albarre Jewelry.

Make her sparkle with this Armenta 18-karat yellow gold and oxidized sterling silver cuff accented with diamonds, $3,225, Elleard Heffern Fine Jewelers.

On Zachary:

He’ll be comfortable and cool in this head-to-toe look—Vineyard Vines sweater ($99), Peter Millar collared shirt ($169), Bills Khakis pants ($275), all from Mister Guy Clothiers.

Gift him this sleek and stylish Bulova watch, $325, Lordos Diamonds.

He’ll hear his favorite tunes clear and comfortably with these Yurbuds Sport Earphones, $60, Big River Running.

On Olivia:

She’ll look chic in this Joseph Ribkoff dress, $291, Marta’s.

Light up her look with this Safia necklace, $800, Marta’s.

Give her a timeless gift with these classic 14-karat white gold earrings with 2.04 carats of white diamonds, call for pricing, Albarre Jewelry.

Her holidays will be bright with this 4.78-carat seafoam tourmaline ring with 1.52 carats of diamonds in 18-karat white gold, call for pricing, Albarre Jewelry.

She’ll surely shimmer in this Line and Dot skirt, $115, Ivy Hill.