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Three Staple Holiday Outfits By Stylist Jessica de Ruiter

When it comes to style, my friend Jessica de Ruiter is a woman who always gets it just right. A stylist and editor, she has a strong sense of self and a distinct personal style that never waivers – classic, chic, and seemingly effortless. With this in mind, I couldn’t think of a better source for holiday style inspiration. During this especially busy time of year, it’s always helpful to have special go-to outfits on hand, and Jessica was kind enough to share three of her favorite Jenni Kayne ensembles. A look for the home that transitions to a sophisticated yet comfortable look for daytime, as well as a decidedly dressed-up ensemble for evening. These three looks will carry you through this festive season, and all the get-togethers on your calendar. See below for Jessica’s holiday picks, as well as her favorite details and the inspiration behind each. XXJKE

DAYTIME – Sophisticated Comfort

Silk Pajama Tunic Shirt and Silk Cropped Pajama Pant, Jenni Kayne
“So easy yet so elegant, these pieces effortlessly move from day to night. This relaxed silhouette is totally on point. I like that the pant is cropped – it makes the look feel feminine – and that the top is more of a tunic than a traditional pajama set. And of course, I love that they’re black silk.”

Black Wool Cashmere Fisherman Sweater, Jenni Kayne
“When I’m cozy at home with my family, I like to be comfortable and select stylish yet functional pieces. This sweater is timeless and so luxurious. I’ll wear it with everything, from layering over my silk pajamas for extra warmth to pairing it with denim and a coat.”

Western Sahara Shearling Slipper, Brother Vellies
“These slippers are so fantastic…they’re a total statement piece, and I had to have them the moment I laid eyes on them! They are definitely not your conventional slipper, which makes them all the more fabulous.”

Black Woven Cashmere Slim Coat, Jenni Kayne
“I’ve always loved a classic car coat – it’s my favorite outerwear silhouette – and I am always drawn to a masculine/feminine component in styling and dressing. Coats are such an important element in one’s wardrobe and I believe something to be invested in. A great coat can last you for years and allows you to wear pretty much anything underneath – from jeans and a t-shirt, to a cocktail dress, to pajamas – and you will always look polished and pulled together. I like to wear mine draped over the shoulder when weather permits.”

Black Ponyhair Mule Slide, Jenni Kayne
“I tend to gravitate towards a slipper style shoe, whether it’s a pointy mule or a men’s smoking slipper. They go with everything and are perfect for errands, brunch or a holiday concert. I am especially loving a flat with black tie and dressed-up holiday party looks”

Lisa Grande Ring, Sophie Bille Brahe
“I chose to pair a minimal gold and pearl ring with this outfit because I think it’s essential to add a touch of femininity when styling a look with a masculine element – and jewelry is a great way to do this. A string of pearls would be too traditional, but the single pearl on this clean band adds just the right subtle detail.”

Black Crossbody Bag, PB 0110
“I chose this cross body bag by PB 0110 because it’s so versatile and works for every season. I often carry my bag like a clutch at night, but if I needed a hands-free moment while shopping for gifts or chasing after my daughter, I could easily throw it over my shoulder for a more daytime look.”


EVENING – Elevated Elegance

Black Silk Midi Dress, Jenni Kayne
“The cut of this dress is sophisticated without being overly-formal. The longer hem length and sumptuous silk fabric make the dress feel elevated and more appropriate for an evening even, yet still young and fresh. I also think the slit in the back brings a beautiful and subtly sexy detail. The definition of easy elegance.”

Black Leather Chelsea Boot, Jenni Kayne
“I paired the boots with the dress because it’s totally unexpected. I like a flat shoe with a cocktail dress – heels are so predictable.  And this boot is cut to the perfect ankle height. It would also look great with a cropped pant. I think showing a little bit of ankle bone is quite flattering. Also, these boots have a nice toe shape – not too pointy and not too round.”

Gold Barrette 021, Sylvain Le Hen
“I find this barrette to be as functional as it is beautiful. Sylvain Le Hen’s pieces are stunning and so unique…special objects unto their own. Available in gold, silver, and rose gold, each colorway looks so pretty in a variety of hair types.”

Lisa Grande Ring, Sophie Bille Brahe
“This ring is the perfect combination for me because I love yellow gold and pearls. I like that the pearl is the gem (as opposed to a diamond!) and how simple the band and setting are – nothing else is distracting. It’s clean and minimal, which makes the pearl feel less precious.”


Photos: Yayo Ahumada