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Classic Tailored Fashion Over 40: Interview With The Style MD for Women, Jennifer Connolly

tips for classic tailored clothing for women over 40

Hi, this is Tina Boomerina. I’ve never been all that good with "traditional" tailored clothing because I’ve always looked better in boho styles (hey, we can’t all look good in the same things) and I don’t want to waste your time with clothing tips that don’t come from firsthand experience. Fortunately, I’ve met another blogger, Jennifer Connolly, The Style MD, who has worked as an image consultant and has experimented with her own wardrobe to determine what types of tailored jackets, jewelry, and accessories she thinks are best (on herself and on many others). And, even if you’re hardcore bohemian, some of Jennifer’s tips about tailored clothing may give you new ideas.

Here’s my interview with The Style MD, and I hope some of you fashion designers are listening:

read about tips for classic tailored outfits

The Style MD, Jennifer Connolly: Fashion Consultant

Q. Tina Boomerina: You have great style, Jennifer. How do you describe your fashion style?

A. Jennifer, Style MD: I have a little bit of a clothing "Sybil" in me. I love many styles of clothes, but what I always come back to is classic. Elegant and classic. My core basics, pants, skirts and jackets, are in neutral colors and unmemorable shapes.

Q. Tina Boomerina: I love the phrase “unmemorable shapes”.  And, I need your help. Lots of readers ask me where to buy good tailored clothing, but I don’t really know what to tell them because I look better in flowing boho outfits, so that’s what I buy. Jennifer, where do you shop?

A. Jennifer, Style MD: For years, my favorite place to find classic pieces was Ann Taylor. Their silk suits were exquisite. I can still find nice stuff there, but I have to pick and choose carefully because their fit model changed... or maybe my body changed.

I also like to shop at Nordstroms, Eileen Fischer (mostly tailored pants with stretch), Macy's and boutiques. I find specialty boutiques give me the best bang for my buck. Not everyone is wearing what I have and it's usually got a slight twist to it.

I like to feel polished and pulled together.

I didn't grow up on the wrong side of the tracks, but I could hear the train from my neighborhood.  At 58, I'm not out to impress anyone but myself, with my wardrobe, and when I look good, I feel good! The majority of my wardrobe is black, with accessories adding the color. You'll also find me in gray, taupe, cream and navy.

Tailored Jackets and Pantsuits for Women:

Q. Tina Boomerina: When I was younger and had to wear tailored clothing, I always had a hard time finding a good jacket. I still have a few of my jackets, but I don’t wear them often because they’re not quite right. What do you look for in a jacket or a pantsuit?

read The Style MD's fashion tips for women over 40

Classic Tailored Styles for Women Over 40

A. Jennifer, Style MD: There's nothing I love more than a garment with simple, clean lines in a luxurious fabric. Just like the moths in my closet, I prefer natural fibers. The softest cottons, silk, cashmere, and wool.

Because my body has sharp angles, tailored garments fit me best. However, I like them in knit and jersey fabrics. My blazers have "give" to them and always have a touch of Lycra or Spandex so they "move" with my body. Stiff woven fabrics look bulky and awful on me.

I prefer jackets with shawl colors rather than peaked lapels. They look more feminine on my squarish frame. Because I'm pretty flat chested, double-breasted jackets and coats look good on me. I love the sway of them hanging open. That extra drape adds softness to an uptight jacket. I also like pants with flow. A wider-legged, high-wasted pant with drape. Think 30's and 40's.

read clothing tips on boomerinas.com

Shawl Collars Are Feminine

(Tina Boomerina: Oooh, knit jackets! What a great idea. And, I need movement to feminize my broad shoulders… so I will try leaving my jacket open the next time I wear one. Those ideas really help me. Seriously… I’m not just saying that. Your tips will probably help other women, too. )

Q. Tina Boomerina: I can see you like pearls. Jennifer, what are your thoughts on accessories?

A. Jennifer, Style MD: Classic tailored clothes can look stodgy and old-ladyish on me unless I funk them up with accessories. I love scarves, necklaces and am a huge fan of bracelets. I go for impact with large accessories because, although I'm short, I have a large frame.

I have a collection of vintage pins from antique markets. I like large ones, 3-4" sized, which I wear very high on my front shoulder, to draw the eye to my face. I always wear one on a winter coat...unless it's leather or suede.

I like to buy accessories on vacation. They make terrific mementos. My very favorite scarf in the world is velvet, the blue green of my eyes that I bought at duty free in London, 25 years ago. I keep accessories forever.

read about classic tailored clothing in my interview with The Style MD

Add Color With Scarves & Accessories

Accessories get loaded in one place. Either multiple bracelets on one arm and no necklace, or necklace and no earrings. Matchy-matchy creeps me out. My earrings NEVER match my necklace. I have scarves from all over the place. Two Hermes, which were gifts, and a special favorite Karl Lagerfeld from the bottom of a bargain bin at Neiman's in New Jersey.

I used to have great luck shopping at Loehmans, but they've gone belly up so now I hunt the sales. After-Christmas sales at the expensive department stores have some amazing deals on classic basics. Saks is overcrowded with merchandise they couldn't sell before the holidays and they need to dump it!

I have friends who love to have a variety of "fake" designer handbags. It makes no sense to me and screams “insecure”. As though they're buying things to impress others, rather than themselves.

(Tina Boomerina: Oh, I totally agree. Sometimes, real designer bags are not as good as unbranded leather handbags – without a label.)

Jennifer, Style MD: Pearls on the other hand, can be faux, freshwater or the finest South Sea, I love them all!  Even the cheapest, plastic pearls you can buy, look elegant to me. They elevate any and every outfit. Dressed up or down, pearls are always appropriate.

Q. Tina Boomerina: I love your pearls. Where did you get all those beautiful, exquisite pearls and other necklaces? Did you inherit some of those from your grandmother?

A. Jennifer, Style MD: I didn't inherit any pearls from "Granny" so I started collecting them myself, in my 30's. I started with a single 18" strand of freshwater pearls on our first vacation to Hawaii. The following year, I bought a 20" iridescent purplish green strand at Macy's Super Sale after Christmas. Two years later, trapped in steerage aboard the flight from hell, I treated myself to an 18" faux strand of large gumball-sized baroque pearls, which quickly became my favorite. I adore them!

Ten years later, for my 30th anniversary, I twisted my husband’s arm for a 17" strand of South Sea pearls in the exact bluish-green color as my eyes. I also have real David Yurman and faux Stella and Dot pearl earrings, which I love...equally. I did inherit an Austrian Crystal bib style necklace from my Granny, which I love to wear with black.

I can be wearing jeans, a classic V-neck sweater with flat shoes...and just the addition of a pearl necklace (or two) makes me feel classy.

read fashion tips at boomerinas.com

Wear Pearls & Necklaces With Everything, Even Jeans

Q. Tina Boomerina: I love what you were wearing in your video. How do you choose an outfit when you want to look your best onscreen or in photos?

A. Jennifer, Style MD: I tried several jackets and sweaters for my video... ultimately I chose the soft ivory sweater for several reasons. The color didn't overpower me... which is who I wanted you to see. Second, it had a slight nubby texture, which downplayed the texture (wrinkles) on my face. It's a great trick. You can do the same thing with pattern... but I don't wear pattern.

On second thought, the only patterns I do wear are narrow stripes and small polka dots. Usually in  black and white. And, what I wore showed up against the black ultra suede chair I was seated on.

Q. Tina Boomerina: Have you always been into classic styles or is this something you’ve embraced after you hit 50?

A. Jennifer, Style MD: I have always liked classic clothing. It just looks rich and classy to me. I also like to mix it up with dramatic and creative pieces to add some spunk.

read about tailored clothing for women over 40 50 60 - tips at boomerinas.com

Neutral Basics for Tailored Women's Clothing

Many years ago, when I managed a very avant-garde boutique, I toyed with highly creative, Italian clothes. They seemed so sophisticated to me. But ultimately, I felt like a fraud. Yes, I had to wear them to sell them, but they weren't me. I felt very conspicuous in them. Uncomfortable. These were seriously bizarre looking. Wild patterns and loud colors...the antithesis of what I feel chic in, even though they were extremely expensive.

Q. Tina Boomerina: Any final thoughts? What do you like to wear? I have a feeling you always look great.

A. Jennifer, Style MD: Most days you will find me with a classic pant or jean, cashmere sweater, suede or leather jacket and dressy flat shoes. I'll have a scarf on, pearls and always have my makeup done. I love hats and wear them religiously in the summer. If I'm going to a lunch with friends, you'll find me in a pencil skirt, cashmere cardigan, buttoned closed and worn like a pullover, my charm bracelet, amongst a stack of bracelets, knee high riding boots and my long black belted trench coat.

read how to wear tailored clothing without looking old at boomerinas.com

Jennifer's Louis Vuitton Satchel

I only carry a satchel handbag. Shoulder bags wrinkle my clothes and ruin the line of the garment... plus they throw my neck out. I use a classic umbrella with a full-length wand and a curved handle. When it's raining I hook my handbag over the umbrella handle so I have an empty hand.

You will never find me wearing sneakers unless I'm at the gym. Ever.


Author Bio: Jennifer Connolly

Jennifer writes A Well Styled Life, a lifestyle blog where she shares her daily inspirations and style tips. She is passionate about simple, elegant design; fashion that is effortless and wearable. Jennifer appreciates simple pleasures, great style, and a life full of wonderful family and friends. She loves to cook and spends many hours creating organic masterpieces in her kitchen.

After many years in the fashion industry working as a boutique manager, stylist & buyer, Jennifer trained to be a professional Image Consultant and Personal Stylist. This gave her the opportunity to help clients find their unique, personal style and build their self-confidence. She ran her Image Consulting company for many years until she and her husband began traveling more.

To read more about Jennifer, click link for A Well Styled Life.

More Fashion Articles for Chic American Women:

Spring & Summer Bag Trends for 2015

Trendy Color for 2015: Yellow Green Lemon Lime Custard Chartreuse Citron Clothing - I'm Digging It

(and the article we all love to hate right about now) Best Swimsuits for Women Over 40, 50 & 60 accccckkkkk!!!

read tips for tailored fashion for women

Main Photo - Tailored Women's Clothing

Photo Credits: Prshots.com and Jennifer Connolly.

  • Main Photo: DuneUK
  • The Style MD, Jennifer Connolly, Fashion Consultant: Jennifer Connolly.
  • Classic Tailored Styles for Women Over 40: WallisUK, LaRedouteUK (3).
  • Shawl Collars Are Feminine: Jaeger, LaRedouteUK.
  • Add Color With Scarves & Accessories: CrewClothingUK, (silk scarf) JaegerUK, (bright scarf) BoticcaUK, (coral scarf) Accessorize.
  • Wear Pearls & Necklaces With Everything, Even Jeans: (the Style MD driving her RV wearing pearls) Jennifer Connolly, (faux pearls) JaegerUK, (coral necklace) DebenhamsUS, (bead & faux pearl necklace) JaegerUK.
  • Neutral Basics for Tailored Women's Clothing: LaRedouteUK, WallisUK.
  • Jennifer's Louis Vuitton Satchel (which I love): Jennifer Connolly.

What do you think of this article? Are you into tailored clothing or boho clothing or do you wear both? Leave a comment at the bottom of the page.

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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  1. mileah curtis

    I recently connected with Jennifer and I'm so glad to see her featured here!!

  2. M-T

    Great interview, Tina, but, there are so many beautiful, elegant layers to this Lady, that you could do many, many more interviews and never exhaust the possibilities. I should know -- Jennifer and I regularly indulge in 2-3 hour, bi-coastal phone conversations about everything from life, fashion and style to the Highs and Lows of Blogging (she's an expert in that field, as well).

    Bottom line -- I feel privileged to call her friend and colleague.

    Cheers, M-T

  3. Tina-Boomerina


    I finally came up with the right description of your style. You are Parisian Chic. And, you have inspired me to wear my pearl earrings today.



  4. Jennifer

    Thanks for the interview Tina! You asked great questions:)
    We all just need the right tools to be and look our best. If I can help or inspire women, I'm thrilled to do it.
    And Tina... whether those Pearl earrings of yours are real or faux, they'll make you look and most importantly, feel elegant. It's all about how we feel and that's boosted by how we look. Looking chic doesn't have an expiration date!
    xx Jennifer

    • Tina-Boomerina


      I did wear the pearl earrings and I felt elegant. I wonder if people treated me better because I looked better or because I felt more confident. Either way, people did seem nicer when I wore my pearls.

      It's such a simple thing, but it made a huge difference.

  5. Jo Jo

    Where is the video?

  6. Jet

    Hi Tina, a well done interview, especially since it out of your (self-admitted) wheel house. It had great follow-up questions and seemed an organic give and take that lent itself to very, very exacting answers from Jennifer, of which the ones I enjoyed most, were about her jewelry, which was retraced through romance; the romance of travel, and the romance of a loving husband, from whom she could plead for pearls.

  7. ~julia/bleu

    Love the new website, glad i'm on the list. Great article. But here's my beef - with every photo posted, could you just chop off their heads? ~chuckles~ ... it is SOOoooo frustrating to read and search and scan and delve thru photo after photo after photo to TRY and find SOMEthing! ANYthing that resembles 'Us'. I hate constantly seeing clothing navigated towards our generation but being worn by young women. Why O why can they not (the fashion industry) See that the boomers dictate a LOT of $$ into what trends for our generation and actually have women model not granddaughters. Sometimes I just want the world to function in reality, not fantasy. If we're paying the bucks, why aren't we dictating how it is presented? Let's here it for Older Female Models ... i KNOW they are out there! So in the meantime, (like the Queen of Hearts that we are) i say, "Chop off their heads!" and only display the clothing, not the child wearing them. Sound extreme? ... perhaps ...

    • Tina-Boomerina


      I totally understand. I've thought of chopping off their heads. But, personally, I don't love chopped off models. Although, I will try to add a few from time to time just for you.

      I've also thought about posting big yellow smiley faces over the models' baby faces... but I think it would be distracting and you wouldn't notice the clothing I'm showing to illustrate my point.

      I DO WISH someone would give me the option of using an older model for at least SOME of the photos.

      The pics I use are mostly from PR companies in the UK, and I don't think they would like smiley faces on their photos. I've asked the PR people to use older models, but when they did, they had the models wearing old-biddy clothes. If I could paste the older faces onto regular clothing, that might work... but I like to use photos I have authorization to use... for FREE... and that's what these are.

      Hey, even if I paid for photos of "middle aged" women, I couldn't find anything to use. Check it out. Look up stock photos of "seniors"... the keyword to use in a search. All the stock photos have older women looking like they've taken a few hits of marijane and washed it down with some Valium-laced margaritas... talk about happy, smiley faces. I suppose it is possible to find pics of older women who don't look deliriously happy (give me some of those drugs), but those photos wouldn't show the right clothing.

      I've written a whole article (actually a swimsuit article) somewhere about this subject, but I don't have time to find the link.


  8. Tina-Boomerina


    Out of my wheel house? I'll have to look that one up.


  9. Mintchip

    This info is wonderful and the pictures are fantastic and beautiful. I'm going to be a drag when I say that if most Boomerina's looked like these gals we wouldn't be having clothing problems in the first place. Miss Tina please relate to MY life!

  10. Shelly

    Hi Tina, I appreciate the beautiful clothes marketed to women over 40, but I am rather insulted with the 20 or 30 year models. Understand my point please as I feel like it's the same as marketing to an African-American woman but having a white person model it. I am not ashamed of my age until I come across 30 year olds who are intentionally used to represent me . We celebrate beautiful younger women. With your beautiful clothes and your style, you can help to bring respect and dignity to us who are older by celebrating our unique individuality with true representation. Thanks for reading.