How to dress after 40 and still look hip?


How to dress after 40
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Of course you can dress any which way you like, but if you don’t want to look like you are sixteen, like you are trying too hard to stay young, or worse, appear older than you are, you will need some guidelines as to how to dress after 40. Here are just some of the things women over 40 need to be aware of.

Please note that these are just general guidelines. They certainly don’t apply fo everyone. I offer my best advice for dressing and style in my 10 Steps to a More Stylish You course. More info at the bottom of this article.

What are some of the things you should avoid?

1. Don’t buy clothes that do not flatter you, even if it’s the trends this season. For this it’s important to know your body type, which I will discuss in upcoming posts.

2. Try not to be too matchy matchy or too polished. It’s nice to mix things up and be a bit more playful. A 2 piece suit will quickly look old. Better to mix that jacket with another skirt or pants and look effortlessly chic.

3.  Avoid buying fabrics that are too cheap as they are usually not flattering or will not last. Best to buy only the clothes that you love and that have a chance of lasting.

4. Don’t mix a tight skirt or pants with a tight top. Aim to have either a tight skirt with a loser top or vice versa. See also my tips on how to wear leggings over 40.

5. Clothes to avoid:

  • really short shorts
  • coloured cowboy boots
  • mini dresses (but do wear those over trousers)
  • miniskirts
  • mom jeans
  • ripped jeans
  • baggy jeans (see also how to wear jeans over 40)
  • unfitted blazers
  • baggy sweats
  • too long skirts

What are some of the things you should do more of?

1. Have more lasting high quality items in your wardrobe. Some important classics are:

  • A white button down shirt.
  • A long coat (could be a trench coat).
  • A beautiful dress that fits you perfectly. Don’t automatically go for a little black dress. Many women over 40 will actually look better (and slimmer) in a colorful dress.
  • Well fitted long pants.
  • A well fitted blazer.
  • A good pair of dark denim jeans that fit you well. Boot cut or straight leg is usually the most flattering.

Focus on creating the nicest silhouette for your body type. I often refer to creating a golden ratio or a 1/3 – 2/3 balance in dressing which is discussed in more detail in my style ebook.

2. Mix and match designer items with non-designer ones. I personally love Zara for many of my fashion items and basics as they carry items in pure cotton or pure wool.

3. Take a good critical look at yourself before you go out and see if you look too overdone. The aim is to look effortlessly chic so just evalueate and if necessary you may have to add on something a bit more casual

4. keep current with the fashion trends and make sure you have a few current items in your wardrobe. Only pick those trends that work for you!

5. Develop your own style. Really discover what works best for your body and stick to that. If you can this well, you will have very little need for the real fashion items.

6. Wear skirts that are just above or on top of the knee which is the best length for women over 40. Try not to go too far over the knee  as this is not flattering for your calves and your overall look will be older. You will look the sexiest and chicest if the skirt is not too wide and not too long. For more info see my article on the perfect skirt length for women over 40.

7. Play with accessories like belts, jewelry and hats. They can make a real difference to your outfit.

8. If you want to hide some of the bulges, then shapewear definitely helps. Learning how to cover with the right clothes also helps, like these tips in the article how to hide your belly.

9. Make sure you wear a good bra.

10. Wear shoes with heals that you are able to walk in. Mid high heels can look fabulous.

I want to exphasise that these tips are not set in stone and it’s up to you to decide what works best for you. But if you want to look young and hip, then these ‘rules’ can certainly help. Stay tuned as I will go more into detail about dressing for your body shape which is so important into looking just right!

For more tips, see also this related article:  How to dress over 40 – my top ten tips

If you like to know more about your body type and which garments would be good for you, I recommend trying My Private Stylist. Get your own personal recommendations!

If you like to improve and discover your own unique style,  I highly recommend my own 10 Steps to a More Stylish You course. In 10 days you will understand so much more about your own body, personality and style and will know what you need to do to take it to the next level. Find out more and get instant access!

If you want to make sure, you never miss an article and to get the best tips straight into your inbox as well as a free latest trends report, be sure to subscribe to the weekly newsletter.


If you have any further tips then I would love to hear them!

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{ 20 comments… read them below or add one }

Tracy (The Wardrobe Wanderer)

some great tips here! My fear when dressing is that I’ll look like I’m trying too hard, or trying to look younger than I am. I think it looks terrible when someone my age or older is wearing, let’s say, really tight ripped up jeans and a top with a huge word boldly splashed across its front, and wearing it off of one shoulder….super high stilletos, gaudy jewelry and overdone makeup. It just looks pathetic, unfortunately. Luckily for me, that sort of look was never my style, even when I was a teen, so it’s not hard to avoid it. I still think about it though when I’m shopping or dressing….’is this age appropriate for me?’ I really want to remain playful and stylish, but I don’t grab just anything that catches my eye anymore.



Thanks Tracy. I think you can still look very hip and be very creative with your clothes over 40. But as you say there are some things that you can better leave to the younger generation…



Amazing information. Thanks Sylvia. I’m straight or banana type with 41 inches bust 36 waist and 42 hip. I’m 5 feet 6 inches tall. Please suggest what kind of clothes should I wear. I’m 40 yrs old.



Hi Vinita, Check out my article on How to dress the rectangle body shape. That should get you started.


ruth ramos

Thank you so much for all this information. i need a wardrobe makeover and this has helped me a lot. I really appreciate it.



Thanks for your kind feedback Ruth!


Kim Steadman

These tips are very helpful. I am 44 years old and love love love fashion! i am constantly balancing my ever growing wardrobe to make my hubby happy (he likes jeans and a tight black t-shirt) and my love for trendy clothes along with my professional wardrobe. I realize that I can’t dress with the latest fads even though i would love to! I also love accessories and shoes but am realizing that I need to go with more lower heels now cuz my back can’t handle it anymore. I look forward to reading the rest of your blog.

Now onto finding what to wear for my body style… I am short (5’2″ and around a size 10 or 12P) and hourglass figure with a little of a tummy and bigger chest (36DDD).



Hi Kim, Glad that you enjoy my blog and find it helpful. For your body type you way want to have look at my article on how to dress when you are petite: I have yet to write an article about dressing for larger bust sizes, which I will do shortly.



I am 41 and I don’t feel like there are rules for dressing over a certain age, at least not yet :) I think this post is PERFECT for most women.



I disagree – There are Rules for dressing you should follow when your over 40 – Im 46 – 5’10 1/2 and I find that if I wear certain clothes I can look like mutton dressed as lamb. I don’t wear mini skirts in public, I find myself dressing in black and nothing else. I have brought my FIRST EVER pair of fitted pants just below the knee. They look groovy with a my high heel ankle boot.

I would like to see more dressing for women who are tall.



Hello, I am 42 yrs old- can I wear cowboy boots with a dress, or is that too young?



Yes for sure. It’s not too young but I do think you need to be careful with styling them as they can have quite a wide fit over your calves which is not always a very flattering look.



I abide by a few rules:
1) Wear trends/fads as accessories
2) Never too tight, too low or too much
3) Simple cuts and mostly solids
4) Don’t wear anything like a teenager or 20-something would
5) Hide your flaws, accentuate the positive



Some great rules!



Hi Ms. Sylvia,
Thank you for these very helpful advises on how wear clothes. I have just bought these long maxi dress (46 inches long) from the net, I am 5 ft (152 inches) only. Please give me advise on how to wear this. Thank you very much.



Hi Adel. This question is also addressed at this article on how to dress when you are petite For any further questions on how to dress it is best to ask them in the style forum


Lena Tilak

I am 42 yrs, I think I look like a barrel with 204 lb my burst 45, waist 43, hip49. I don’t know what to wear any more.



You can look good no matter what you body shape is Lena. Start with this article and find out your body type. Then follow some guidelines for your specific body type and start exploring!


Laura C.

I’m a rectangle so I looked at your suggested site Zara. Yuk! Most of those shirts and dresses look like G.C. Murphy and dime store (think Big Lots now) leftover rags from the 70s. Young models with bellies showing in short tops-cute for them but those items are not suitable for women over 40 even superfit women in shape. Get some real suggestions for us that will work so we don’t all go shopping and get something that “will do” but is not very attractive or flattering.



I offer suggestions all the time in close to 400 articles already on the site. Fashion changes all the time, so if Zara had good things one season, they may not do so necessarily the next. Also, Zara is a shop where you need to be picky. A lot of things are for very young women, but I still use it as a go-to shop for myself as there are always things that are good for us too. If you want to read more suggestions for the rectangle visit this page: I also have a page of other good shops for women over 40 here: If you want to understand why we can’t feature only 40+ women in fashion posts, you may want to read this article:


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