Don’t Let Anyone Tell You What to Wear! 7 Fashion Rules to Break Over 40!

Fashion Rules to Break Over 40

Do you remember that show, What Not to Wear?? With the 360-degree mirror, the constant sarcasm, and the sign in the intro that said “No mini skirts over 35!” I think they meant well with the show, and no disrespect to the show hosts or creators… But they did take a more negative approach to dressing over 40 and aging in general. As I’ve gotten older, I’ve noticed that the more “rules” in place for women over 40, the more triggered or resentful I feel. Why? Because nobody wants to be told what to do! And I don’t want you to EVER feel like you can’t wear something just because someone said you can’t or because it’s a “rule.” So in this post and corresponding video, I’m talking about each of the common “rules” that people have come up with for women over a certain age…and we’re going to debunk them! I’m going to show you how to wear these things that we’re “not supposed to wear” in an elegant, classy, sophisticated, and FUN way that will have the naysayers questioning their own rules!

If you’re still struggling to determine your personal style and need some guidance, this post is a must-read!

Fashion Rules to Break Over 40

Fashion Rule #1) Don’t Wear Mini Skirts

Because I mentioned the mini skirts sign that rubbed me the wrong way in the intro of What Not To Wear…that’s where we’re going to start! I first want to say that if you don’t want to wear any of these things…you don’t have to! Fashion is supposed to be fun and make YOU happy. So, if you don’t feel happy in a mini skirt, don’t wear one. I happen to love my legs, so I like to wear mini skirts and dresses.

This first look is one I wore on a trip to Texas and took in front of this cool art installation. I’m wearing a sequin mini skirt and a matching blazer by Alice + Olivia. I LOVE this look but you definitely don’t have to go all-in with a sequin mini skirt. Maybe you try a mini dress or mini skirt and style it in a more casual way that feels more wearable for you. Play around with what makes you feel comfortable. During the summer, you can always add some Charlotte Tilbury lotion to add a little shine. Or try a nice light reflective lotion so your legs have a bit of a glow. Or…just do what you’re comfortable with! When wearing a mini skirt or mini dress during the winter, you can always wear tights (seen below in Rule #2). Tights keep the look streamlined and create that elongating line. I also love tights for covering up any skin imperfections or insecurities on my legs.

I talk even more about insecurities and how I’m reframing how I look at my body in this corresponding video so make sure you watch that! Plus, even more mini skirt outfit inspiration.

alice + olivia black tuxedo dress

Fashion Rule #2) Don’t Wear Plunging Necklines

Have you ever put on a top that was a little low cut and thought it wasn’t classy or elegant or that it was just “too much.” You can absolutely wear plunging necklines! Again, it’s about your comfort level, what makes you feel good, and what makes you feel sexy. If plunging necklines make you feel sexy…go for it! If you look at the tuxedo dress I’m wearing above, you can see that it has a deep v-neck that’s considered a plunging neckline. I could wear a camisole underneath it to add some coverage. But I think it’s really sexy without it and I love the plunging neckline. It looks very classy and elegant. A little more about this dress and the outfit…I love the black and white contrast. It’s very classic and makes me feel powerful. I paired it with some black tights and ankle booties.

You can play around with different v-necklines to see what makes you feel comfortable and sexy, but it doesn’t have to be a super deep V if that’s not what you’re comfortable in!

Fashion Rules to Break Over 40

Fashion Rule #3) Don’t Wear Leather Pants

Wearing leather, faux leather, or coated pants is SO sexy, modern, and edgy. When I’m wearing leather pants, I feel SO confident! In this look, I’m wearing a pair of cropped flare leather pants by Frame with a pair of stiletto booties by Schutz and a double-breasted blazer by Veronica Beard. This look is really cool, edgy, modern, and sophisticated. The key is mixing the “rule-breaking” piece (the pants) with the more sophisticated, classic piece (the blazer). It creates a really elegant look. You can also go fully sexy if you wanted to spice it up with a plunging neckline. But it’s really important to think about breaking these rules in a way that feels best for YOU. You have to feel confident!

black cutout top, see by chloe flared jeans

Fashion Rule #4) Don’t Wear Cutouts

Can you wear cutouts after a certain age? Absolutely, yes! Do they look cheap or trashy? Absolutely not! Do they look sexy, modern, and elegant? Heck, YES! This mock neck sweater by Fore has one very strategic cutout at the neckline that shows off a very sexy, but modest part of a woman’s body…her collarbone! I can still wear a regular bra with this top, the neckline isn’t too high (so that neck skin isn’t gathered and I’m not too hot), and it’s more fitted and body skimming. The small peek-a-boo cutout is very classy but still has that modern twist! I styled this top with a pair of flared jeans but I’d wear it with leather pants, trousers, and a blazer, or a chic pleated midi skirt. It’s very versatile and wearable.
There are also cutout pieces out there that show off a lot of skin on the midriff. I have a dress that I love that has a small strategic cutout on the side that creates the illusion of a smaller waist. So the key is really finding those pieces that have strategic cutouts in places you feel comfortable with.

I share even more about how to wear cutouts, what to look for, and more in this post if you’re interested.

crop top over 40 fashion

Fashion Rule #5) Don’t Wear Crop Tops

Crop tops, bralettes, bra tops…whatever you want to call them! They are often a piece we shy away from as women 40+. But there are definitely ways to style a crop top that will make you feel covered and confident. My personal favorite is to wear a bra top with a blazer over it and some high-rise pants or jeans. The blazer helps skim the sides while the high-rise pants help give you more coverage over the lower tummy. If you have some killer abs, wear the crop top on its own and rock it! But if not, try these style tweaks like the blazer to make yourself feel more comfortable.

how to wear a romper over 40

Fashion Rule #6) Don’t Wear Rompers

For those of you who don’t know, rompers are just the short version of jumpsuits. I happen to love rompers because I’m petite and I like my legs. They can be tricky to style if you’re really tall or have a long torso. But if they work for your body type, they can be really fun, elegant, and sophisticated. In the spring/summer, I wear rompers all the time and I’ll even wear them in the winter with tights and booties. The Alexis romper I’m wearing above is a really beautiful example of the kind of romper you can try if you’re 40+. It has long sleeves to offset the shorter hemline, the neckline is really sophisticated, and I love the removable belt that helps cinch the waist. It’s pushing the envelope a little, but I really LOVE it and it makes me feel happy!

red blazer, pink karen millen pants

Fashion Rule #7) Don’t Wear Loud Colors & Prints

Is it true that bold colors and loud prints are hard to wear? Yes. Does that mean you can’t wear them at all over 40? NO!

I’ve talked a lot about prints and colors in the past and how to style them. But my biggest tip on wearing prints is to find bold but small-scale prints so they aren’t so overpowering. Or wear bold solid colors instead. The outfit I’m wearing above is a great example of how to wear bright colors. It’s pretty bold, but I wanted to share a BIG example so you could then take pieces of it to try on your own. Maybe you just wear the bright blazer with black trousers or the bright pants with a white blouse.

I’m wearing a red Alice + Olivia longline blazer with some hot pink boucle flared pants and pumps. This is an unexpected color combination but such a gorgeous one! A color-blocked look like this is a great way to push the envelope and conjure those feelings of joy and happiness in your wardrobe. But it doesn’t have to be this bold right off the bat. Another option is to try a color pop like a bold-colored blouse, bag, or shoes, a bright-colored lipstick, fun nails, or a new eyeshadow color. You can make little tweaks to try it out!

I shared another way to style this color combo in this video where I recreated looks that Sarah Jessica Parker wore.

Don’t forget that you can watch the corresponding video that goes along with this blog post here or below.

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Thanks for stopping by!

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