I remember being in my 20s and seeing "older" women who had clearly gotten stuck in a decades old look like a bouffant hairdo or blue eyeshadow or shoulder pad suits. Now I'm in my 40s and I like to think my look is timeless and just my own personal style but I'm wondering if I actually look dated, with my shoulder length wavy hair, wrap dresses or cigarette pants and wrap style blouses, and wedge heels. Thoughts?

It’s hard to judge yourself. I feel the same — I buy the same style clothes as I did a decade ago and my hairstyle has not changed at all (but I have very fine hair, so I can only do so much with it). When things get back to normal, I’m going to see a stylist at a department store to get a few new pieces to refresh my look.
Just buy fresh wrap dresses and make sure your wedges are updated. It helps to buy new shoes and not rely on old classic ones even espadrilles and wedge pumps as styles change so much every year...the Little Eric wedge pumps may be the exception they always look great.
Update your accessories regularly to reflect what you like best among current color, texture, style trends. New glasses especially can help, without having to change your basics.
I’m sorry but I have to disagree with the wrap dress & wedge thing... there is a whole world of fantastic, creative clothing out there. Please don’t limit yourself to this. This could be a “youthful” look for someone in their 50s or 60s, but I honestly thing it could age a 40-something who wants to put more effort into her style.
Your suggestions are welcome...light a single candle...
Totally get this! I have always said that some people find the look that suits them in their early 20s and then stick with it for life... which is why you see the blue eyeshadow/bouffant hairdos, because they were in their 20s during those times. I have the same self consciousness about whether my look is dated too. My theory is that you don't have to embrace all new trends (and honestly that makes you look way too try-hard) but changing little things here and there keep it more fresh. I think it helps a lot to change your hair a bit if you can - ask your stylist how to make your cut or color more modern, etc. And certainly makeup trends change a bit too and you can adopt those if you know that they'll be good on you. Maybe a new shape for eyeglasses, or getting pointy pumps instead of round toe, etc. I always find it helpful to find a celebrity my age to look to since they have stylists etc and rarely look old and dowdy. For example, Julianne Moore and Jennifer Aniston are both over 50 and manage to both look age appropriate and stylish but not like they want to be 20 again.
I 100% know what you mean. I’m in my 30s and have been thinking about this lately. As I get older I want to dress ”age appropriately“ (ie, sophisticated as compared to what I wore in my 20s) but still stay aware of trends. The trend thing is important to me so that at least I won’t be like the mom who wore her 10 year old low rise boot cut jeans and stripey highlights in 2016 b/c she didn’t realize things changes. Some things I do: 1) maintain a “personal style” Pinterest board that I update periodically, 2) casually follow seasonal fashion shows and trends and pick what flatters me and is age appropriate, 3) choose style icons I model my style after. I usually like what Victoria Beckham, Queen Letizia of Spain, and Olivia Palermo are wearing so I just follow them season to season based on the couple new pieces I might need. To me they all hit nice but varying balances of classic vs. trendy. I have similar coloring to them too, so I watch their hair and makeup to make sure I’m looking fresh. Although none of this has mattered much during quarantine :)
You have a Pinterest board? What? You have too much time on your hands lady
Your sn is “Ublifer” and you chose something quite petty to criticize me for... Pot meet kettle
What is wrong with my sn? I am paying homage to our special motherboard, pun intended. I would hardly say that equates to a grown woman keeping a Pinterest board to determine her style for the season. Give me a break. More like pot meet middle schooler.
Try shopping even for just a few pieces a year from updated brands Apiece Apart, Ganni, Zimmerman, or for lower-price, JCrew especially JCrew Collection and The Westside. And make sure you don't recycle the same shoes too many years in a row...
I wouldn’t consider these brands ”updated” tbh.
I feel the same ! In my head, I'm still 25 years old and my simple casual style has never evolved. I think I need a makeover, because to my 10 y.o daughter, I really look my age (45) and she finds my "casual&simple" look, frumpy.