If you’ve ever seen Michelle Williams or Rachel Weisz stun on the red carpet, then you’ve seen the handiwork of celebrity stylist Kate Young. Their chic-yet-packed-with-personality style? That’s Young, named one of The Hollywood Reporter’s Power Stylists of 2014, pulling the strings behind the scenes. Her recent book, Dressing for the Dark, sheds light on the process — it was inspired by the mood boards she creates for each client — while offering an entertaining primer on cinematic style. Plus, it’s rife with handy how-did-I-ever-live-without-’em insider style tips. Here, in the spirit of the holiday season, Young shares some advice on dressing for cocktail hour, from foundation garments to bejeweled finery.

The inspiration behind Dressing for the Dark
I do these inspiration books for my clients. If they have a lot of appearances, I always want there to be a thread of continuity to their look and they help give hair and makeup people an idea of what we’re going for; they set a tone. A friend saw one and suggested I do a book.

Cinematic fashions that first captured my attention…
Audrey Hepburn. It’s almost a cliche to talk about her because she’s such a fashion icon, but there’s something amazing about a career like that. The fashion in so many of her movies was so precise. She was so careful about it and it really did set the tone for her films. A lot of her movies… they made people want to buy black dresses.

Top cocktail-party style tips…
That’s hard. The thing with fashion is that it’s so personal and it doesn’t work unless it matches who you are. Everybody is different — their bodies are different, their lives are different. I think the most important thing is to wear something that makes you feel good. You don’t want to be constantly checking if something is falling down or becoming unzipped. And while a witty handbag can be great, you don’t want people’s first reaction to be “Whoa.” It should be more organic than that. You should wear something that makes you feel confident and makes you feel festive.

My go-to holiday dress…
You know, I’m a fashion girl so I don’t wear the most flattering things a lot of the time. I like to be covered up. I tend to wear black long-sleeve dresses.

Jewelry tips…
It’s important to think about balance — so if you have a bag that’s all crystals, you shouldn’t have rings all over your hand. I think a short necklace can be really aging, so you have to be really careful with it. Like, if you’re 30 and you wear a diamond necklace like that, it can make you look 50. I also don’t really like necklaes in the in-between length; that length doesn’t feel formal to me. Bracelets — I really like it when you wear two cuffs that match. That’s one of my favorite looks.

Clutch essentials to avoid on-the-scene fashion emergencies…
Sometimes, if a dress is iffy I’ll give my clients some tape or a safety pin to put in their bag, but that’s it.

The right foundation garment for a strapless dress…
Wear corset bras instead of a strapless bra. Our tendency with strapless bras is to always want to yank it up and that’s probably the most unattractive thing you can do. When it’s a longline bra, it stays anchored and doesn’t fall as easily. If you have small boobs, you can use stick-on bras.

Other underpinning tips…
Butt pads. If you’re wearing a structured dress and you don’t have hips or a butt, your waist can look thick. Butt pads will make it look smaller. I know it’s sort of counterintuitive — we all think we want to look smaller all the time — but your waist will look smaller if your hips are a little bit bigger. I’m also obsessed with the Embracer from Victoria’s Secret; it’s my favorite waist cincher.

To avoid VPLs…
There’s a Commando seamless thong bodysuit that I love — that thing is amazing. It slims and controls and it’s also totally invisible if you wear a sheer blouse or a sheer dress. For bras — Chantelle is the best. It has a lined cup and a bit of support but doesn’t leave any lines. It’s like the best T-shirt bra. And it also makes a very natural shape, not padded and ridiculous. Underwear — Commando thongs and boy shorts.

For heel comfort…
I really believe in shoe pads. If a shoe is uncomfortable but you want it anyways, buy it a half-size bigger and put pads in. They really help. I recommend Foot Petals.

Pairing heel heights with hem lengths…
I think it’s more about trends rather than the length of the dress. For a long time I thought super-high platform heels were so chic and now they look cheap to me. But I have some clients who are teeny-tiny and, if the dress is really long and you’re not going to see the shoe, I’ll put that platform under there. I do love a flat with a gown, but you have to be six feet tall to wear that.

And when it comes to stockings and dresses…
I really like sheer black stockings. And stockings with Swiss dots — I think they’re so sexy. There’s this picture of Diane von Furstenberg, with her legs crossed, at Studio 54… Is there anything better than those legs with the dots on them?

Most memorable holiday party…
It was 1997, I was an assistant at Vogue and the Vogue Christmas party was at Balthazar. Madonna was there. Karen Elson and Erin O’Connor were there, looking so cool and awesome… They were wearing jeans; they didn’t dress up for it. And outside there were all these fur protestors. Anna [Wintour] sent them a giant plate of steaming roast beef with a note saying, “We thought you might be cold and hungry.” It was fabulous.

Favorite charity…
Shoe 4 Africa.

Read more features from Holiday Issues, past and present.

On home page: Kate Young, photographed at her New York office by Mimi Ritzen Crawford; above, from left: Michelle Williams, Natalie Portman, Rachel Weisz and Diane Kruger, all pictured in Young’s book, Dressing for the Dark, from Assouline

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