Close this search box.


Photograph from Edition01

I’m joining my friend, Cindy Hattersley, as we each interview a different woman for our monthly “Ageless Style” series.

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

Share this Story

Hi Girlfriends,

I’m proud to say that 1010ParkPlace™ has been voted one of the Top Ten Blogs for women over 50: the best-educated, wealthiest, most powerful demographic in history.

Here you will get a glimpse into the lives of other women, learn how they handled things life put in their path like divorce, the death of a spouse, serious health issues, low self-esteem, addiction and how to reinvent yourself after a major life change. You will find like-minded women and relevant conversations about finances, fashion, sex, books, music, films and food. We feature interviews with inspiring women along with straight-talk and bold conversations to reawaken your passions and make life count.

Brenda’s Blog has between a 58.4% and a 68.7% click thru rate, which is unheard of. My readers tell me it’s because I’m sassy and transparent, they trust me and no topic is off limits.

Tell your girlfriends, sisters and coworkers about 1010ParkPlace. We have lots of exciting interviews planned and stay tuned for updates about my memoir! 

#WhereStyleIsAgeless   #MakeLifeCount   #WhatAreYouWaitingFor


  1. She’s beautiful Brenda and she’s had such a fabulous career. I’be had breast cancer twice and it takes a lot of strength to keep going when we don’t know the future. Wishing her all the best.

    • I’m sorry to hear you’ve had breast cancer not once, but twice. As a one-time breast cancer survivor I know I will never breathe a sigh of relief because it can always return. Scary stuff, cancer. Blessings to you, Arlo. xoxox, Brenda

  2. Hi Brenda

    I love Ann’s attitude and style. Thank you Ann for the fit flop tip. I am off to check them out. I haven’t worn heels for years either. I am 68 and not about to sacrifice comfort for style at this age. Ann offered so many practical tips and wisdom. What a great interview. I thoroughly enjoyed it.

    • You’re a love, Cindy! I’m enjoying doing the Ageless Style posts with you. Thanks again for asking me. xoxo, Brenda

  3. I love the list of basic pieces we should have in our closet. They all make sense, but I have some shopping to do!

  4. Ann you look like a twenty year old!
    Can’t be if you were wearing the RL style back in the day!
    Off to instagram to find you!
    Great questions Brenda fun interview!
    Tuscany is getting close!!!
    Are you already packing in your head?

    • Elizabeth, Isn’t Ann gorgeous? She’s beautiful inside and out. I’m packing for Tuscany in my head, thinking about things I’d like to take, but also remembering my rule about one carry-on and a duffle bag. One of the other women who’s coming said she could do that if she only took clothes that were silk. Yep! I’ll have lots of silk. xoxox, Brenda

  5. Ann wears clothes beautifully! Wow! And I love her suggestions for the kind of clothes we need and she’s right. Thanks for a great interview Brenda!

    • Hi Edie, Thanks for leaving me and Ann a comment. I appreciate that you read it and shared your thoughts. xoxox, Brenda

  6. I agree FIT Flops are amazing. Especially if you have foot knee or back issues.
    And it’s good to know I’m not the only one who can’t travel light. 3 weeks in Mexico took 2 big suitcases, one was the personal care and hair stuff and one was clothing and then the carry on held shoes and I also had a big purse and a backpack!! TRAVEL LIGHT?? WHAT”S THAT?? LOL…

    • Belinda, Travel light? LOL! My habit began in my twenties when I explored jungles and abandoned silver mines. On those trips I needed a big hat… huge hat, long-sleeved shirts and jeans, and lightweight long pants. Since then I’ve stayed at hotels in Europe where they had stairs, no elevator, and no bellboys to help me, and I had to lug my bags up and down multi flights of stairs by myself. Now, I don’t want to lose my bags to the airlines. xoxox, Brenda

  7. Well, you just sold tons of FitFlops. Love your style. Wish I could wear it. I’m with you about packing. I take way too much. One carry one? What an interesting career. Can’t wait for your trip blogs Brenda!!!

    • Thank you, Sandy! I met a woman at the bank today who knew me because the two of you met on an island off the coast of Washington and when she said she was from San Antonio, you told her to follow me on Instagram. How fun! Thank you, sweet lady! xoxox, Brenda

    • Thank you, Kim! Glad you enjoyed my interview with Ann. She’s amazing! Packing light? Habit, honed over years of adventure travel where there was no one to carry my bags and sleeping in a hut in the jungle with a skinned squirrel that dripped blood on my forehead. Not the right environment for fuzzy bathroom slippers, dinner dresses, and lots of makeup. I did carry my pink, SONY boom box and lots of heavy batteries!!! LOL! Music was/still is my priority. Oh, the people I met in the jungle because I had the Bee Gees and the Rolling Stones. Now I pack light because I don’t want the airlines to lose my luggage. Ten days in Italy without my stuff? No way! xoxox, Brenda

      • Ann is the epitome of chic. Her relaxed, giving nature shines through. I have long admired her beauty and the presentation of her Instagram posts. Ann is truly a survivor and role model for all of us.

        • Wonderful to see you here, Maura! Thanks for stopping by and leaving me and Ann a comment. Ann is all those things and more, so I was thrilled when she agreed to let me interview her. Hope to see you here again. xoxox, Brenda

  8. Thanks for the FitFlop reference Ann and Brenda. Like both of you I no longer can sacrifice comfort… let’s call it what it is… WALKING… for style!

    • Betty, Yes. Walking… Across the room. Thanks for reading and letting us know we’re not the only ones who seek out comfy shoes. xoxox, Brenda

  9. I love her style, clean lines and classic pieces. Seeing a woman who dresses well is a reminder that I’m never sorry when I buy good clothes and look sharp. Cost per wear… I’ve heard you talk about that Brenda. It makes sense. Thank you!

    • Thank you, Audrey! Ann’s style is similar to mine. Quality classic pieces we’ll have forever. Thanks for remembering that I’ve written about cost per wear!! xoxox, Brenda

  10. What an interesting post. I did a nose dive into Amal and George style pics though! ‍ Ann is truly a beauty and thanks for the Fit Flop info…checking it out now!

    • Hi Gray! I love seeing you here! Happy you liked Ann and our conversation. We can learn a lot from her. I’d love to have her choose fashions for me sometime. xoxox, Brenda

  11. What a vivacious and stylish woman! Appreciate her list of closet basics and comfortable shoe recommendation too. I’m with you on the light packing. Thank you for introducing us to Ann, she’s amazing!

    • Hi Ginger, I’m so happy you enjoyed meeting Ann, and I agree… Her suggestions for shoes and closet basics are stellar! Thanks for letting us know. xoxo, Brenda

  12. I enjoy your blog very much and hope you will continue it! Any chance you might blog about packing for Tuscany and help some of us learn how to pack light but well?

    • Thank you, Dinah! I appreciate that. This last year has been the first time since I’ve started blogging that I haven’t had a blog every week. I never missed until I wrote a book, and now I’m doing revisions, which are equally as challenging. Packing for Tuscany and packing light: great idea for a blog! I’ll put it on the calendar. Thanks so much! xoxox, Brenda

  13. Great post Brenda! I enjoyed getting to know about Ann. In one of the other comments, someone said they’d love to have Ann style/dress them. Add me to that list as well. You and Ann have a lot in common being breast cancer survivors and beautiful women who dress well. So much to learn from both of you. Thanks, Xo, Barb

  14. Ann has such style! I bet she turns heads where ever she goes. That red scarf is bold and dramatic. Thanks for this one Brenda.

    • You’re welcome, Mickey! Ann is stunning and I agree with you about the red scarf. Would love to have a long one like that in my closet. Brenda

    • Hi Doreen, I’m so happy you have an all-clear from your doctors! You’re in my prayers every day. I hear you about chemo and feet. Mine too. I can’t think of a part of my body that isn’t still affected by chemo, but I’ll take it! I’m still here! xoxox, Brenda

  15. Enjoyed this so much, Brenda! Ann is an inspiration in many ways. I love her classic, yet elevated style. Much to learn and absorb here … lots of common sense and wisdom. Thanks for the flat and sneaker ideas … heels aren’t my thing anymore either. xo

    • Hi Juliet, No heels for you either? I hear you! They are a painful problem when we lose the fat pads on the bottom of our feet. Love seeing you here! Thanks for stopping by. xoxox, Brenda

  16. I love Fitflops from Italy. I found my mules with a little wedge heel at TJ Maxx. I haven’t seen their sneakers there or the ballet flats so I’m really glad you provided the links. I want my Fitflops in my closet. Thank you for a lovely interview. Going to check Cindy’s post now.

    • M In Hi, Thanks so much for reading and leaving me a comment. Fitflops are a must for my closet as well for an upcoming trip to Italy. Hope to see you here again, Brenda

Comments are closed.


Sign up to our list and we’ll send you our sought-after guide “50 Ways To Change Your Life”
I'm happy you've joined us! If you like what you read, I'd love for you to stay and subscribe to our updates by email. We have a great community of like-minded women, and your presence can only make it stronger.