What not to wear when you’re almost 40

This post contains affiliate links.

The links in this post may be affiliate links.  That means that if you click them and make a purchase, this site makes a commission.  It will have no impact on the price you pay or the experience of your purchase.

I'm turning 39 next week, aka officially “almost 40”

I'm the textbook definition of old, according to 9 year old me… I remember when my parents turned 40, and how very ancient I thought they were at the time.

As I approach this impending birthday, I decided to start thinking of myself as 40 already, you know, to get used to it and everything. So I started doing some very important internet research to figure out how to be a grown-up. (I figure 39 is as good a time as any.)

A good place to start? My closet. If I have the costume down, then everything else will surely fall into place, right? Of course this is how it works.

Almost 40 search results

There are so many handy articles and posts about how you're supposed to dress, I decided to analyze as many of them as I could and then distill their feedback down into a single post for you. 🙂


almost 40 - chucks

I definitely need to get rid of my beloved Converse. These aren't grown-up shoes at all. Forget that they're classic casual wear, and are available in fun prints like these Andy Warhol soup cans. They're for teenagers and 1970s basketball players. I'm neither of those things, so out they must go.

Also taking up space they don't deserve on my closet floor are these novelty flats from ModCloth. Grown up ladies don't wear shoes that make them smile. Shoes are meant to protect your feet and that's it.

almost 40 - flats


This is a wide category, and it can be so very easy to get carried away and find yourself with things that are totally inappropriate for an adult of your generation to wear out in public. No matter how cold it is, this Star Wars scarf is not something that I should ever be seen in. Her Universe may make loads of cute geek-related things, but I'm clearly too old for it.

almost 40 - star wars scarf

It is not acceptable for a grown ass woman to express her fandoms or things she enjoys through her clothing. Again, this is for teenagers, not me. So I'll be getting rid of my collection of novelty earrings as well. Even though they're tiny and only people who look closely even notice them, I should only be seen in tasteful studs in gold or silver. Perhaps a colored gemstone if I'm truly feeling adventurous.

almost 40 - nintendo


This is where the list and specifics get long. I'll be clearing out all of the prints from my closet that aren't tasteful florals or traditional plaids. I may be able to keep a polka dot or two if it's subtle and not too colorful. I can wear lots of black with the occasional “pop of color,” but it general I should live in neutrals only.

For work, all of these prints will have to go right out the door. Sorry, LuLaRoe, ModCloth, and eShakti. I'm too old for fun prints for the office now. It's all sensible knits and machine washable fabrics from here on out.

almost 40 - novelty prints

My errand running outfits also need revision. I shouldn't be wearing anything that can be described as “distressed” style= because it implies that I fancy myself a 20-something who “doesn't know any better” So clearly, this outfit is going straight into the donation bag.

almost 40 - distressed and kimono

I'll also have to change my formal event choices. My Iris Awards dress, while fun at the time, was apparently completely inappropriate for me, and if I'd wanted to have had fun with my fashion for this event, I should have stuck with adding some sequins or maybe even an off the shoulder look. Those are much better choices for actual grown-up ladies. All those people who complimented me that evening were wrong, apparently.

almost 40 - irisawards

fashion takeaways

(aka: I have all the answers now!)

Speaking as a woman who is a mere 7 days away from being a mere one year away from being 40, this makes me an expert. I've read many articles on this here internet, so I basically have a Ph.D. now. And it all comes down to this:

Wear what you want. If you want a capsule wardrobe, do it. If you want to live in black yoga pants and Look Human pop culture tees, more power to you. Does catching your own reflection in the mirror make you smile? You're wearing the right stuff. Are you happy and comfortable in your clothes?  Rock on. Do they pinch in uncomfortable ways? Buy a bigger size and be happy that you aren't uncomfortable. Do you share your fandoms, opinions, political beliefs, favorite foods via t-shirts and legging prints? You're the best.

Don't let someone tell you what to wear and what not to wear. Seriously. Every single thing I've shared in this post is something that I own, love, wear, and will continue to wear past my 39th birthday and beyond.

Similar Posts


  1. You scared me for a moment. I thought we might have to have an intervention 🙂 I totally support the wear what you like and rock it idea! I even own those modcloth kitty flats myself.

  2. If it makes you feel good, go for it. For me, it’s all about comfort. Which sometimes means LLR leggings with flying pigs on them. 🙂

  3. I have seen so many of those articles and they drive me batty! I agree with the idea that you shouldn’t be trying to look 20 but that usually means having the confidence to wear what you love and not what Forever 21 tells you to love;). Your style is adorable and you best not change it! Now excuse me while I go see if I can pick up those super cute flats!

    1. There were a couple of versions… I don’t know if they have those exact striped ones, but I definitely saw varations! Like pink with a grey kitty!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.