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How to Look Hot: Women Over 40, 50, 60

by Tina Boomerina (Christina Gregoire)

Boomer Chicks need answers. We may be women over 40, 50, or even 60, but we still want to look hot.

Well, burn the bad and keep the good.  And, try these amazingly sexy ideas.

sexy old ladiesI have read a lot of articles and books about looking hot over 40.  Well, one article says to show cleavage; the next one says not to show anything. It’s absolutely ridiculous. Those websites are telling you what looks good on them.  And, their solutions may make you look like a bag lady or a chickadee from slutsville.

So, let’s start with my street cred: I am 59 and I am a Baby Boomer with an average body and very thin hair. Not much to work with, is it? Well, I make do.  And, if I can. You can.

No Halter Tops or Tanks?

One article, says to throw away anything with cleavage unless you want to be mistaken for Samantha on “Sex and the City”. OMG! I want to be mistaken for Samantha. Is that all I need to do? Show cleavage.  You got it, buster.

Well, not everyone needs to show cleavage. However, if you are overweight, showing a little skin is a good way to draw people's eyes away from your bad parts. And, on some women, boobs are the last thing to go. And, that would be me. I just spent ten days on Maui in some very low-cut, one-piece bathing suits and sarongs to cover my white-ass heinie. Did I look like I was 20? No. Did I look like the other fat old ladies in high-necked T-shirts and shorts? No. I looked better.

how to look sexy over 50Hey, if I looked good in high-necked T-shirts and shorts, I would wear them, but I don’t. I use tricks.  Long V-neck tops and long U-neck tops make my fat neck look longer. If you are tall, thin and gorgeous, showing cleavage would probably come off as desperate on you. Everyone is different. Remember that all online advice is coming from someone who has found what looks good on them. If we all looked good in the same thing, we’d be airbrushed Stepford Wives.

Hot Over 40 & 50 – Pants

If you look good in classic cuts, preppy shirts, and LLBean styles, you will look good in straight-leg or bootcut trousers. Hey, if you look good in those, you’ve got it made. Everything else will probably look good on you. So, baby, you can wear bootcut jeans ‘til the day you die.

However, if you look better in Boho Chic, as I do, your best “jeans” may be leggings in black or denim, worn with long sweaters that hit you at mid-thigh. That’s the style I try to rock because my weight sits in my tummy and skinny leggings make my legs look thin. Then, I tuck my leggings into high-heeled boots to make me taller.

Some articles say that women over 50 should wear cropped pants. Oh, no. Very few women look good in those things unless they are very tall and thin. Well, some women who are extremely round look good in capris, especially on cruise ships, because capris draw people's attention to their thin ankles. But, these women are the exception to the rule.

Hemlines on Older Womenlow cut dress for women over 40 50 60

Some women become sex kittens in knee-length pencil skirts. So, if you look good in those, knock yourself out.  I know I'd wear them if they looked like that on me.

For the rest of us females, I like to see trendy chicks wearing slightly shorter skirts (about an inch or two above the knee) with matching tights. Black is easy to wear, but you can try other fabulous, dark colors like rich chocolate or perky navy.  And, you might want to throw on a lightweight trench coat in a smashing color for that Euro-Chic look. Then, you should pull on some boots or booties with a “sturdy” 3-inch heel for extra height and sex appeal.

In summer, you can wear a wrap dress (with a low V-neckline) or a belted shirtdress to get the same look. Yes, you can wear boots or booties in summer. But, if you hate short skirts, try long, silky, Boho skirts.  I find that women who wear their hems at mid-knee are screaming to the world that they are little old ladies... but maybe that's just me. (article continues)

Keep reading about how to look sexy when you're older on page 2.

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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. lily

    I truly love your suggestions re leggings and cleavage. I have plenty of both, but I'm often unsure of when to rock them.

    I'm divorced, nearly 64, look ten years younger and feel 20 years younger. Because so many women friends my age are a) married homebodies, b) too depressed to leave the house, or c) just plain boring, I mainly socialize with people in their 30's and 40's. I have no desire to dress like them or look their age, and I'm told I have great style. I wear leggings all winter, usually with tunic sweaters and boots. However, I needed your encouragement to wear them with dresses. I was afraid it might look as if I was trying too hard, but you have given me new confidence.

    As for the cleavage, my "girls" didn't show up until around menopause, when I grew (without synthetics) from a 34B to a 36D. So, now that I have them, I appreciate the lesson in when and how to employ them as part of my overall look. I especially like the advice about the "deep V" and "deep U" to balance out a fat neck. So THAT's why I always feel more confident in my lower cut ballet jerseys.

    I stumbled on to this site by accident. Clearly, there are no accidents. THANKS! I'll be back often.

  2. Christina Gregoire


    You should wear what looks good on you. Forget what other people tell you to do (especially online fashion "experts" who talk about what looks good on them)... the "experts" who have never met you and have NO idea who you are and NO idea what you look like. And, be happy that your ta-tas decided to blossom around menopause. Lucky you. Most women just blossum in their tummies during menopause.

    On the other hand, I'm also glad you look good in the same things that look good on me. I love that style. I love low-cut tops (well... you know, within reason). I love leggings and boots. And, for some reason, high-necklines just look terrible on me. Well, I can wear higher necklines if I have a very long necklace (usually a long pendant or the very long necklace I made with huge irregular pearls) and if the top I'm wearing is in the right color. So, experiment... but don't listen to old people - or young people. You can tell when something looks good (on you) by the way people in the grocery store or Starbucks treat you. (male and/or female)

    And, I understand about finding "girl" friends who aren't old biddies and who aren't afraid to go out and do things. (I was divorced for years.)

    I thought most the people "our age" who grew up with all the fun stuff like Beatlemania and disco, etc., would continue to redefine hipness forever. Have they just given up? That makes no sense. It doesn't take a lot of money to be creative. You just have to think for yourself and not be afraid. Some of my favorite tops are from Walmart. (I bought them years ago. Wish I could find more.) Tee shirts from Old Navy are the best. Travel can be cheap (see the Rick Steves' books for Europe). Stay at the Edison Hotel (good price and next to W) for NYC fun. Stay at a downtown hotel (with a pal) in your own city and walk around. Walking is good exercise. Much more fun than a freaking treadmill.

    As for fashion, you can wear boots and leggings with almost anything. It sounds like you have your own style. Once upon a time (back in the 90s) I wore black booties with a short black skirt (above the knee)... before it was "in style." A friend said, "I didn't know you could wear ankle boots with skirts." Well, I was astounded. They're my booties. They're my feet. What the heck. (And, they were the only black boots I had at the time. But, no one needed to know that part.)

  3. Christina Gregoire

    ps Lily, the fact that you're hanging around with younger people proves that you're doing something right.

  4. Rose

    Thank you, thank you, thank you. To reiterate... we can wear what makes us feel good. We are not dead yet. Others only wish they had some style...Today before finding this article I bought 4 new pairs of shoes... yippee yi yay! You've made me laugh and justify my yearnings.

    • Tina-Boomerina


      That's so true. I love that you bought 4 pairs of shoes. No matter what size we are, there are always cute shoes online somewhere.

      Tina Boomerina