Fashion Rules You Should Never Break Over 40

Heather Anderson
by Heather Anderson

Are you a rule follower or a rule breaker? I’m generally a rule breaker, but there are five rules for fashion over 40 that I believe should never be broken. They’re tried and true and they work every time.


But, as always, take what you like and leave the rest! You make the rules for yourself.

Fashion over 40

1. Always dress for the occasion


Tom Ford famously said “dressing well is a form of good manners”.


Dressing well to me means dressing appropriately for a specific occasion. So unless the invitation says otherwise, dress up for a wedding. You can’t go wrong in something like this fabulous slip dress that I’ve paired with metallic sandals and bag and a satin jacket.

Fashion over 40

If I was going to a softball game, I’d dress very differently and very casually. Perhaps in these distressed shorts, a gauzy button down and flat slides.

Fashion over 40

One of my golden fashion rules is “if in doubt, overdress” because in my opinion it’s way better to be overdressed than underdressed.


Here’s an example of a friend and I dressing up for an influencer event we attended. My silver bomber jacket, designer bag, shoes and belt are definitely on the dressier side, even though I paired them with a midi length ivory denim skirt.

Fashion over 40

2. Wear the correct undergarments


That means for example, don’t wear a black or even a white bra under a white t-shirt unless you intend for your bra to be seen as part of the outfit.


My favorite thing to wear under a white top is a nude-coloured bra or nipple stickies.

Fashion over 40

The other mistake I see women making is not wearing Spanx or something similar under form fitting dresses or skirts.


I’m wearing my favorite pair of high waisted Spanx under this close fitting skirt and matching top to smooth everything out and hold it in. They’re so snug I seriously think they make me look 5 lbs (2 kg) slimmer.

Fashion over 40

3. Don’t wear too many trend pieces at once

Your wardrobe should be made up of 80 - 85% basics and 15 - 20% trend pieces, and you need to keep that in mind as well when you’re putting together an outfit.


Vests are a big trend now for spring and summer, so my denim vest is the trend piece in this outfit. I paired it with a beautiful satin maxi skirt and added a silver bag and shoes.

Fashion over 40

The trend piece in this next outfit is also a vest, this time in sage green and worn open over a bodysuit that I tucked into my denim maxi skirt.

Fashion over 40

4. Dress in clothes that make you feel confident

This is probably the most important rule of all, because confidence is the best accessory we can wear.


Pay attention to how you feel when you wear something. If you’re thinking of wearing shorts but you hate your legs, then don’t wear shorts. If you don’t love your arms, don’t wear a sleeveless top.


Instead, wear things that make you feel confident by accentuating your best features.


Wear form-fitting clothes to show off your trim waist. If you have beautiful sexy legs, wear shorts and mini skirts.


Style knows no age. It’s all about wearing clothes that make you feel like the best version of yourself.


I love form-fitting clothes, so here’s that satin maxi skirt again, this time teamed with a very simple, casual white tank. Then I draped a short sleeved cropped denim jacket over my shoulders.


It’s a look that really showcases my figures and is perfect for a date night.

Fashion over 40

5. Follow the ABC rule


ABC stands for Accentuate, Balance and Camouflage.


Accentuate your best features, as I covered in the previous rule.


Balance out the look. If you’re wearing a mini skirt or a pair of shorts you want to cover up the top portion of your body, and vice versa. That will create elegance and class in your look, as well as balance.


If there’s an area of your body that you don’t love or that’s a bit of a challenge for you, cover it up or camouflage it. Don’t draw attention to it.


Not everyone might agree that a mini skirt is appropriate for a 50 year old woman but I work out a lot and I love my legs, so I feel confident and comfortable wearing one. That’s the key.


I’m also balancing the look with a tank top and jacket on the top half of my body.


Fashion over 40

I hope you found these fashion hacks useful. Fashion style over 40 can be challenging, but these five rules I think form the basis of looking good and feeling confident.


I’d love to know in the comments which look is your favorite.


Next, check out these 8 Easy Outfit Combinations for When You Have Nothing to Wear.

The author may collect a small share of sales from the links on this page.

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