How to dress after 40 and still look hip?

by Barbara

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 to 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. Know your style! Nothing is more important than dressing in a way that pleases and represents you. If you know your style and understand your body you can break any of the rules or add items from the ‘don’t list’ as you please. My style course will help with that.

2. Determine the wardrobe essentials that are unique to your style.

3. Have more lasting high quality items in your wardrobe. These vary for each style personality but 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.

4. Mix and match designer items with non-designer ones.

5. 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.

6. 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! If you want to know about the latest trends you can subscribe to my newsletter and receive a free trends report!

7. Wear skirts that are just above or on top of the knee which is the best skirt 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.

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

9. If you want to hide some of the bulges, then shapewear definitely helps. If you don’t like shapewear, then learning how to skilfully hide with the right clothes also helps, like these tips in the article hw to hide your belly.

10. Make sure you wear a good bra. More info in my article on how to find the perfect bra.

11. Wear shoes with heals that you are able to walk in. Mid high heels can look fabulous. If you need more support I have a great list of arch support shoes.

I want to emphasise 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. The more you understand your body and your style, the more you can break these rules as you please.

For even 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.

Enjoy!


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

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{ 48 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.

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Sylvia

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…

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Vinita

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.

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Sylvia

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

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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.

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Sylvia

Thanks for your kind feedback Ruth!

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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).

Reply

Sylvia

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: http://40plusstyle.com/how-to-dress-when-you-are-short-petite/. I have yet to write an article about dressing for larger bust sizes, which I will do shortly.

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Krista

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.

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Dee

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.

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sam

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

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Sylvia

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.

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Darcy

I’m 46 and I wear cowboy boots with dresses almost every weekend. Or even with a jean skirt. I even wear red boots, green boots and multi colored boots…I wish I could upload some pictures. I do not agree that a colored cowboy boot after 40 is a no.

Reply

Sylvia

As I mentioned Darcy, these ‘rules’ are not set in stone and really depend on each individual’s style. Clearly colored cowboy boots are a part of your unique style and I’m sure you look great in them. You are very welcome to upload photos to my Facebook page (https://www.facebook.com/40PlusStyle) and I will share them with all followers. I would love to see you rocking those boots!

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Sockpuppet

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

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Sylvia

Some great rules!

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Adel

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.

Reply

Sylvia

Hi Adel. This question is also addressed at this article on how to dress when you are petite http://40plusstyle.com/how-to-dress-when-you-are-short-petite/ For any further questions on how to dress it is best to ask them in the style forum http://40plusstyle.com/forum/

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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.

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Sylvia

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! http://40plusstyle.com/how-to-determine-body-shape/

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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.

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Sylvia

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: http://40plusstyle.com/how-to-dress-the-rectangle-body-shape/. I also have a page of other good shops for women over 40 here: http://40plusstyle.com/best-online-shops/ If you want to understand why we can’t feature only 40+ women in fashion posts, you may want to read this article: http://40plusstyle.com/fabulous-40-plus-women/

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Robyn Kearns

I’m 46. 5’4″ and I weigh 150. People tell me I look young. Which is a good thing. :) What is a proper dress length just for casual days? I am very classic as far as style goes. Thank you

Reply

Sylvia

I wrote an article about skirt lengths that would apply to dresses as well. Although I personally prefer on top or just under knees slightly higher will work too. It comes down to your personal preference. http://40plusstyle.com/what-is-the-perfect-skirt-length-for-women-over-40/ When I’m on the beach or holiday, I tend to go shorter with my dresses.

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Helen

I don’t give a f@#! about rules, I am over 50, work out, and wear what ever i like that looks good on me and those who don’t like it can kiss my firm and mascular glutes!

Reply

Sylvia

By all means Helen. These ‘rules’ are only there for those that like some guidance. You will find that we break these ‘rules’ frequently here at 40+Style and have lots of fun with style and fashion!

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RMG

I think the most essential thing is to count on the expertise of 20-something clerks in women’s clothing stores. If one of them tells you that a piece of clothing makes you look “young and hip”, you should definitely buy it.

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Helen

I don’t count on the “expertise” of the 20 something or any other age sales assistant!
I look at three things:

1 – Do I like it?
2 -Does it look good on me?
3- Will it make the “age appropriate” dress police enraged?

If it ticks all 3 boxes, then, I will buy it!

https://www.facebook.com/pages/Ernestine-Shepherd-Worlds-Oldest-Female-Body-Builder/116632508372892?hc_location=timeline This woman is 76, looks great and wears staff that would make the age appropriate dress police froth in the mouth!!! She is my inspiration and I aim to be like her when I am that age!

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Sylvia

wow, what an amazing woman! If you want to be like her though at that age, better start working out now…

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Helen

I do work out, diligently, have been doing so for about 3-4 years, 5 times a week, weight training and bodyweight exercises, eat properly, I am 5.4, tall, weight 58 kg, wear size 6 US and have 18% body fat, which is regarded as lean. http://www.builtlean.com/2010/08/03/ideal-body-fat-percentage-chart/

My tummy is flat, I have visible triceps, quads and firm, rounded butt. I can bench press 40 kg for 10 reps, do about 30 push ups from toes, 12 parallel unassisted dips and 3 unassisted chin ups. In the fitness world my achievements are very modest/mediocre – nothing to crow about. However, how many 50 + women outside the fitness/gym environment to you know who train and perform like I do? Here’s my bench press video on FB: https://www.facebook.com/photo.php?v=552248608205736&set=vb.100002618040492&type=2&theater That’s 47kg for about 4 reps.

Back in 2010 my now ex husband has told me that I will quit in about 2 months! LOL

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Sylvia

I’m impressed Helen. It looks like you are well on your way!

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Helen

Thanks :-)

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Sylvia

Unfortunately not all shop assistants are experts though and many will say anything to sell an item. You will still need to trust your own judgement and go with your instinct.

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Emla

If you have great legs, shorter length shorts are fine.

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Marian Rothschild

Hi Sylvia,

Your readers are in good hands. It’s difficult to find style and fashion advice for women over 40 that I agree with 100%. As a certified personal image consultant and wardrobe stylist, most of my clients are women over 40 who ask similar questions as your readers. So glad they are getting terrific suggestions and pointers to express themselves by choosing styles that they love to give them pop and polish.

Best wishes for much success.
Marian Rothschild

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Martine

Sorry, But I love mom jeans. I grew up wearing low rise jeans. But I am very drawn to high rise jeans, especially vintage ones, like “mom ” jeans. I also like cut off shorts. And i like ripped denim. I love white button up shirts, and white t shirts. I have white t shirts in cotton, silk, and even soft leather. I like macthy match. Of course there was none of that when I was younger. But now at thirty, i want things to match. i LOVE wearing a top and skirt in the same pattern. So chic. Maybe I’m just not ready to grow up.

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Sylvia

Good for you Martine! Ultimately you must do what makes you happy. Anything I say are just broad guidelines that you can choose to ignore.

Reply

Helen

Martine, you shouldn’t have to say sorry to anyone for wearing what you like, life is hard enough without the added stress of having the dress police on our backs!

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Lesley

Great site and sound tips.

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Deb

Sound advice! Thanks so much.

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FashionistaOver40

I really hate it when someone decides that their fashion sense is “the only fashion sense”. Telling people over 40 they shouldn’t wear this or that… Just because you are old and maybe look old, doesn’t mean that all women over 40 appear old, wrinkly and have one foot in the grave. I don’t dress like a 20 year old but dress classy (my friends who are politicians, Dr’s and fashion designers…say so anyway) and am constantly asked my advice on fashion. I just tell people to wear what makes them happy. Most people don’t dress (in my circle anyway) like the “before” on makeover shows on tv, they dress like the “after”. If I want to wear a pair of ripped up jeans, I will. I have a great body, look in my 30’s (I’m not in my 30’s and haven’t been in more than a decade) and when people see photos of just my face, they are shocked that I am my age. I like to wear a more natural make up, my hair more simple and not colored. I am a vegan and take care of myself, don’t drink alcohol, don’t smoke, never did illegal drugs, exercise. SO my advice is that you can wear ripped up jeans if you want and the occasion warrants it (a rock concert maybe?) Maybe don’t wear them to the Opera lol. But it’s up to you to do what you want. People need to be themselves, not try to be what someone else teaches. I have read so many fashion magazines, blogs, watched tv shows, etc. They ALL give different advice on the exact same thing. Fashion isn’t a science, ladies. It is individual. Be yourselves. Who cares if someone else likes it or is jealous of it (of course when people tell me how they love the way that I dress, I do enjoy it). Live, Love, Laugh… and dress for your wants and needs!

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Sylvia

I agree with a lot of what you are saying. And there are quite a few articles on this site that give exactly that message. We also sometimes have some lively discussions! Still, quite a few women like some guidelines and that is what I have given here in this article. Feel free to ignore them as you please. I wholeheartedly agree with your last sentence!

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Michelle

I think this can apply to someone from late thirties and up. I see a lot of women around 39 that dress like teenagers.

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Sabina @Oceanblue Style

Dear Silvia, I also am not a type for guidelines and also dont think it has got anything to do with age at all. I personally feel that there is still a lot of tolerance missing in public opinion. But sharing ideas I find most inspiring. So I would really appreciate your input on my gray-in-gray with white blouse combination! Thank you. xo Sabina @Oceanblue Style

http://oceanbluestyle.blogspot.com/2014/10/elegance-ease-grau-in-grau-geht-das.html

Reply

Sylvia

Lovely layering outfit Sabina and love the grays together!

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Jayne

What a fantastic site! Thank you so much for the guidelines which are there for us to consider for our individuality and personal world. I appreciate it. I have found lately that I’ve got better at the science of working out lengths of tops and bottoms, which height of boot looks best with what and which length of necklace works. I too have been told I look a fair bit younger than my age (mid forties) but still work hard not to dress too young but classic with a hint of chic. I especially love leggings and will be very sad when/if they go out of fashion. Thanks again.

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Sylvia

Thanks for your kind feedback Jayne. Enjoy browsing the site! 100s of articles for you to enjoy…

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Sabina @Oceanblue Style

Oh I love wearing ripped jeans. And if you pair them with a nice classy sweater or coat it will totally created the best effect. xo Sabina @Oceanblue Style

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