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I’m joining my friend, Cindy Hattersley, as we each interview a different woman for our monthly “Ageless Style” series. You’ll find the link to Cindy’s blog at the end of my post.

Other than her style and beauty, the first thing that drew me to Ann Caruso was her kind, empathetic and caring heart. Qualities she’s honed as a respected, international celebrity stylist with big-name clients like Oprah, Elizabeth Hurley, and Johnny Depp, and by her personal experience as a two-time breast cancer survivor. 

Ann Caruso lists the basic pieces every woman over 50 should have in her closet.

Ann Caruso is renowned in the fashion industry for her refined classic aesthetics. She began her career as a design assistant at Ralph Lauren, the iconic American fashion house, followed by seven years at Vogue Magazine. Under the leadership of editor, Anna Wintour, Ann developed a reputation as a well-known fashion and accessories editor. Since then, she’s become a successful freelance stylist and brand consultant, winning the Womenswear Stylist of the Year award. Her work has appeared in Vanity Fair, InStyle, Town & Country, Tatler, and Harper’s Bazaar where she was a contributing fashion editor.

George Clooney asked Ann to dress his family for his Venice wedding to Amal Alamuddin.

ANN: I came to NY from Boston, looking for a fashion job, and I was perfect for Ralph Lauren. I was wearing my turtlenecks and navy blazers and long, riding skirts and jeans with riding boots. That was my look with my long dark hair. I really wanted to work on a magazine and work with different designers and explore my fashion style so when I got to Vogue, I expressed my style in a different way. It became a little bit edgier. 

BRENDA: What is your definition of style? I think a lot of people confuse style with fashion.

ANN: Style is the way someone chooses to express themselves with fashion. It’s a total look, not just clothing. It’s your accessories, your beauty, the way you wear your makeup and your hair, and your personality. It’s a form of self-expression.

BRENDA: How has your style changed in the last few years?

Photograph from Edition01

ANN: I haven’t been dressing up as much as I used to, although I’ve gone to some galas and events, but I think now it’s about feeling more comfortable in my clothes. I’m not interested in feeling the pain for fashion. Several years ago I didn’t care if my feet hurt in the shoes if they were beautiful. I was going to wear them anyway. Now I just want to be comfortable because that makes me feel confident. 

BRENDA: You like dresses, and I love the ones you post on Instagram. They’re chic Boho.

ANN: I’m attracted to the chic Bohemian style even in the winter. You can wear them with boots, or a great flat and a great belt. It’s an easy way to dress and be comfortable. A few years ago I was wearing the straight, knee-length skirt, very Dolce and Gabbana looks all the time. That was kind of a signature look for me. I have a certain clean aesthetic about me no matter what I’m wearing. I’m also attracted to menswear in dressing. Even today I have a v-neck cashmere sweater on with a boyfriend style jean. And I love blazers. If you saw my closet, it’s full of men’s shirts. I have every stripe you can imagine. I have to stop myself from buying another white shirt or another striped shirt because that’s what I’m attracted to.

BRENDA: Do you get them tailored?

ANN: No. I just wear them. That’s the style now. I dressed that way when I was in my 20s as well. When I was at Vogue, I would wear my oversized Brooks Brothers shirts and have my bra peeking out, and have a straight skirt or a pant. That was the look, and I’ve never really left it. I have a row of all these blazers and suits. I’m loving suits. I think you always look put together in them. Especially, the suits in colors like pink!

BRENDA: In my 20s I wore men’s shirts and ties a lot. I still do. It’s funny you said that, because I sent you a link to a blog I did, wearing a suit I bought after breast cancer. Nothing looked good on me so I went shopping for something I could wear to dinner with my husband. My friend, Jack Simpson, makes couture for men, and in that photoshoot, I’m wearing one of Jack’s ties. I still can’t tie a tie, so I wind up going to a menswear department and ask a salesman to tie my tie, and I just leave it that way in my closet.

ANN: I know. It’s not easy. I like how you put the necklace over it. 

Photograph by Rupert Anderson

BRENDA: Do you have any rules of thumb when you buy clothes for yourself or your celebrity clients like what colors look best on them, or maybe necklines and hem lengths that are more flattering than others, or do you find yourself saying to heck with it. I love this piece. It may not be the best thing on me, but I like it, and I’m going to buy it.  

ANN: Everyone’s body is so different and needs different silhouettes on them so there isn’t one rule. In general, an open neck is more flattering than a closed neck, but there are some people who can wear everything and there are some people who have a skinny neckline and are bony and would look better with a closed neck. Sometimes I find someone who’s a little bigger on top looks better with a little open neckline. But I don’t think there’s one rule. 

I think times have changed so much that if you want to buy something that makes you feel good, then you should do it. If it’s not so flattering, but you feel great, then why not? What I usually do is try to buy clothes I know I will continue to wear for many seasons, even if it is trendy I think to myself, can I wear this item for a couple of seasons and wear it in different ways and have options? I try and think about how am I going to get the most cost per wear for my purchase. It has to be worthwhile for me.

What basic pieces should every woman over 50 have in her closet?

ANN: A black pant, a great fitting pair of jeans, a blazer, a trench coat, a good-looking winter coat, a basic white shirt, a beautiful cashmere sweater and scarf, a great suit, a dress that can go from flats to heels, a black dress, a black pump, and I think everyone should have a black evening pump. They’re always sold out so when you find them, you should definitely buy them. Having the perfect flat, and finding a sneaker that works with pants and jeans is a trick. I just found a bootie from Veronica Beard and I ordered another pair in black because I can walk anywhere in them.

I think we need tall boots to wear with dresses, and a clutch is so important. Of course, everyone needs a great crossbody bag. It’s the most important bag to have now because we need our hands free, especially if you live in a city. All of these things you can interchange and wear with all of the other things you wind up adding to your wardrobe.

Photograph by Jenny Gage and Tom Betterton

BRENDA: I have things that have been in my wardrobe for thirty years but because they’re quality pieces I invested in, they haven’t gone out of style, and I can still wear them.

ANN: Me too. My best pieces are things I’ve had for a long time, even shoes. I think shoes were made so much better twenty years ago.

BRENDA: I had foot surgery to remove a blood clot from the arch of my foot caused by the arch in a pair of cowboy boots being too high. The surgery permanently messed up the nerves in the bottom of that foot, and I can no longer wear shoes with a heel, even a lot of flats I can’t wear, so I look for stylish sneakers and comfortable flats. 

ANN: I’m going to tell you a secret. The most comfortable flats and sneakers are FitFlop. 

They have these little ballerina flats. You’re going to put them on, and you’re never going to want to wear another flat from anyone else.

BRENDA: I’m in!

ANN: They have a sneaker, a plain white sneaker, and they have a knit one. They’re so light and made out of something sustainable. I love traveling with them. 

BRENDA: Do you have a favorite go-to outfit?

ANN: In summer, I think my favorite is probably a dress with a sandal. Any other time of the year it’s great fitting jeans with a crisp white shirt or a navy cashmere sweater and maybe a blazer over it. Something clean and simple. The other night I wore black jeans with a black silk top from The Row and had this cashmere vest made by Dovima from Paris. It has a big collar, almost like a peacoat, but it’s a vest. Simple with a pair of boots and I was done. It was clean and sharp. I have Rag & Bone jeans that are a little cropped. 

BRENDA: In April I’m taking nine women to Tuscany. I never check bags, and the last two times I went to Europe I took one carry-on and my Louis Vuitton weekender/duffle bag. I put all of my accessories and beauty products in the duffle and clothes in the carry-on. I try to pack so my tops work with pants and skirts, and I wear my bulkiest items so they don’t have to go in my luggage. Any suggestions for things I should pack?

ANN: You are amazing! I am the worst person to ask. I went to Florida for ten days and I had two huge pieces of T. Anthony luggage and a carry-on and when I came back… I had to pay for overage. One carry-on? I think I would die, honestly. My beauty supplies are like a carry-on suitcase. LOL! We need to forget that question. 

BRENDA: I’ve loved our time together, Ann. Thank you so much.

ANN: Thank you for thinking of me.

Please leave me and Ann a comment or a question and then hop over to Cindy Hattersley’s blog and see who she’s featuring today

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