Chris, I have felt in a fashion rut over the years. I felt drawn to the flower child look but that is hard to pull off in my 50s and 60s. I wanted something that was authentic, minimalistic and interesting. Not too much to ask for!!! I was not a classic dresser but I think I am evolving in that direction.
For me, some inspiration really helps. I found this in a few bloggers whose style met my requirements. They might be in their late 20s or early 30s but that doesn't matter. Style Bee described her style as Jane Birkin meets Diane Keaton. A woman after my heart. See pictures. I am working on how to put this together in my wardrobe.

I also like Efbgen's ideas.

So much good advice here, but I am sorry to hear that you are feeling a bit adrift.

Chris, you helped me through the summer with your light blue / red / white combination. I really embraced those colours and felt very happy with them. The way you articulated your thoughts and then your WIW really inspired me. Thank you! This was the top that especially fulfils that colour combination for me, and a jacket, both thrifted (funny how you find things when you have the inspiration) which I wore with light blue jeans. I know this is off topic, but I did just want to say thank you for your help.

Chris, I feel you've progressed in leaps and bounds in your style and made some superb purchases while here (and some smart returns, too.) But I understand what you are saying. LaPed put it perfectly. Like the two of you, I have a classic style, and live a casual life, and have a strong practical streak, as well as a preppy streak...so it was difficult for me to move beyond jeans and a shirt, i.e. "no style" style. I felt this way very much after my first year or so on YLF. I had reached a style plateau or something and couldn't figure out how to get further.

I'm not sure I am any closer to that now but I'm more content to be on the journey, if that makes any sense. I seem to have less need to pin it all down and am happier to let it evolve as it will. To get to this point I did a few things. (Others have also suggested similar, above).

• Wild card purchases -- my first one was a jacket in an unexpected colour. The jacket was a classic piece; the colour was not my usual. Wild cards remain difficult for me to identify and buy but they usually work out really well and have a high happiness factor.

• Classic essentials with a difference -- i.e. -- if you know this piece is the kind of thing you will wear again and again, pay for quality -- it does make an item feel better and you will love it more!! OR...look for essentials with some added special detailing, like a pullover with side buttons or buttoned cuffs or different type of seams, or some other distinctive, of-the-moment detail.

• You say you're not much for trends. But trends are often nothing but a classic item coming into special vogue (like trench coats or a shape of sunglasses or white shirts or sneakers or plaid, etc.) Pounce on the ones you genuinely love when they are trending. You'll automatically look more current just by being yourself!

• Invest in a more luxe bag. Cost per wear will be minimal if you truly love it and use it a lot and it adds a great deal to an outfit. Ditto, footwear.

Just wanted to say: I think you DO need to stand out a little bit to have style that people admire.

That’s something I’ve been working on and it’s paying off.

I agree with Smittie. I definitely stand out in the land of pine trees and bears. Oh and Santa land.

I like what Suz said! Also there was something on here a long time ago about writing out the style descriptors that youre not (boho, preppy, bombshell, etc), and id add the colors, prints, contrasts that dont work for you. The 180 degree turns.

This is a helpful post. So much useful information.

Smittie and Style Fan, now you’re getting close to my dilemma with a certain red KS bag: would it (make me) elevate my look *too* much, such that it becomes a distraction?

FashIntern, did you post about your red KS bag?

Chris, I know I am late to this thread, but I was genuinely surprised to read this, because to me, your summer outfits have been stylish and anything but boring.

At times I have felt in a style rut. Occasionally I would go off the deep end and buy a wildcard - that was so wild it was unwearable...

I remember the first time I bought a wildcard that worked. I bought some summer sandals that were denim with pretty crystals on them, probably twice as much as the more basic sandals I normally bought, but I fell hard for these. I wore those sandals into the ground because they were practical for my lifestyle. This is the sort of wildcard that you are looking for.

I honestly think you are probably at that wonderful spot - where you have the colours, silhouette and basics sorted so that now you can focus on getting some of those special pieces that spark joy. Just don't do what I did initially and get super impractical wildcards - wildcards that work are the best workhorses of all.

Another thing to add is that style evolves. My acceptance of that has helped make me look forward to seasonal refreshes and closet edits rather than seeing these as evidence of former mistakes.

Bijou, what a great attitude about “evolving” rather than “mistakes”.

Style Fan, I thought I was driving everyone nuts with my posts about that bag, so I’m relieved there is someone who didn’t see them.
https://youlookfab.com/welookf.....bag-search
https://youlookfab.com/welookfab/topic/what-now
https://youlookfab.com/welookf.....ther-one-2

Celia, thanks, and you said it well, the classic cuts are just so easy to wear with our body type (and other cuts are so much more difficult), AND also feel boring after a while as you said. Maybe I have some sort of a craving to have an entirely new wardrobe every season I suppose if that's true I ought to acknowledge it although I don't really want clothes shopping to be the only thing in my life, as fun as that sounds!

efben, you crack me up with the "classic with a nod to casual/sporty. Shocker" :-). I know exactly what you are talking about. Good suggestions on accessories/jewelry/purses etc. I do follow some bloggers online but I find I don't really like reading most of the ones that focus on what "older women should wear" because it's just too limiting. I've done the closet reorg idea in the past and it DOES result in new ideas, maybe I'll try it again. And I love the idea of taking some pieces and building outfits around them. I think I'll do that when I take Angie's advice and put together two great fall outfits. Thanks!

Greenjeans, I'm not exactly sure why I don't feel myself in dresses unless it's for a bit of an event. Maybe if I spent a little more time thinking about this I could figure it out, and it would lead me to some other good ideas.

Style Fan, I can so see you as a flower child back in the day , dancing at Woodstock with bell bottomed jeans and an actual flower in your hair..but yes that style doesn't seem to repeat itself later in life as well as some looks do. I do follow some bloggers but could probably use some new inspiration. Good luck trying to incorporate Style Bee looks into your wardrobe!

Jane thanks, very kind of you, and glad I was able to help. I never did wear light blue/red myself I finally found two dresses in reds so late in the summer that I only wore one of them, and light blue has been so hard to find. That blouse is beautiful, kind of like an old china pattern!

Suz, funny to hear you say you maybe didn't figure out how to move on from a plateau but got more comfortable with the journey...your style just seems so YOU and so well put together. Grass is greener I guess. Your suggestions are terrific, and I'll keep them in mind, although I'm not convinced I'm in a place where I can reliably make good decisions on wild cards and essentials with a difference. I am focusing on bags and footwear right now where I seem to make better choices.

Thanks smittie, good point. I guess you are saying take a bit of a risk with something a bit bolder. Good advice.

Style Fan, HAH! pine trees and bears and Santa oh my! (Doesn't quite rhyme like the original lions&tigers expression from Wiz of Oz). Side note: the FB community page for my very small town has been full of black bear sightings lately. It's a very rural area, although much less remote than where you are I think, yet so many people seem surprised. The weekly police blotter in the local newspaper always has at least one story about sometime calling the cops because "there was a raccoon in my driveway".

Suntiger GREAT idea to include the 180 degree NOTs.

Bijou, thanks, I do tend to be my own worst critic I have had mixed success with wild cards - the nutmeg coat I bought last year is fabulous but works for a very short season. The powder blue sandals from over a year ago not so much...I love them but they are a bit too maximal to go with much (Angie DID say they were maximal). You said it well "wildcards that work are the best workhorses of all." I'm currently thinking hard about some cognac suede booties that fit well and I kind of love but would be very limited seasonally even if I treated them. I need to build up the basic non-limited wardrobe items first, although you are right that I have an ok selection now. Good point about seasonal refreshes vs. mistakes, you have to take them all in perspective and be able to tell the difference.

Chris, that cracked me up about the raccoons in the driveway. Bears walk up our driveway and down the valley. I think their den is down there. The cubs are so sweet. I need to get a picture.

Chris - You always look fab to me. Especially have swooned over your new coats! That being said, I hear you. I have a very classic style and at 58 yo, if it gets too ladylike or expected it feels "old lady." So here's what helps me keep my edge. 1. Haircut. I wear an inverted bob (it's wedged up short in the back and the bangs, well I call them the "angry toddler hack". I make my hairdresser cut them really spiky and jagged like an anime character. So although it's silky smooth (humidity permitting) the line and bangs are edgy. 2. Juxtaposition - very important. The more classic the pieces the more I must have something very rate. Classic blazers with hiking boots, lady coat with sophisticated moto boots, sexy sheath dress with suede booties and moto jacket. Do the unexpected. Pearls and jeans, cropped leather moto and evening gown...3. Mies van der Rohe - "God is in the details" - best quality and best iteration. Fit, fit, fit. No exceptions Good proportions for your body. Best quality fabric and drape. Basics with just that little something extra - what I think of as elevated basics. Silk tee shirt, cashmere tank or hoodie, special texture/weave/detail. That kind of stuff. 4. Ok is not good enough. If you really love the pieces you pick - fit, fabric, proportions, color, details - then you are excited to wear your clothes. 5. Unique - don't run with the herd, unless love where the herd is going. Being an authentic Chris is much more flattering than being a wannabee anyone else. This is why I still rock leggings, black, skirted leggings, hiking boots, heeled hiking boots etc. Anyway, those touchstones help me make better decisions. But you always look awesome to me Chris!!!

Thanks Gryffin! What a very astute comment "if it's get too ladylike or expected it feels like "old lady". That really resonates with me. There is really something your 1 - 5 I'm definitely going to think about them. I was wearing my black Ecco quilted sneakers recently and a friend said she like them and I said I loved them but somehow they often felt off, and her reply was that I need to dye my hair purple and that would fix it. Gave me a good laugh but there is something to the general concept....

Chris, thanks for the compliment and as others have said, I think your summer outfits this year were fabulous. Sometimes we are hardest on ourselves. Also, I love what Bijou and Gryffin said -- you want wildcards that work, and too ladylike feels "old lady." I agree it is really hard to identify those workable wildcards but as Bijou also said, creating a wardrobe is a process of evolution and it is okay, even necessary to make what later seem like mistakes as we go along. Meanwhile, as someone who's retired, you are fortunate in that you can dress more casually and it's easier (I think) to aim for juxtapositions when not dressing for a stuffy corporate environment.

Re dresses: I never wore them except for "occasions" for years. What switched it all up for me was first, the tube skirts (super casual & comfy and below the knee) followed by this year's casual summer dresses, which worked so. much. better. for me than pants or even shorts in our extreme heat. I didn't ever feel "dressed up" in them -- just relaxed. But finding dresses like that is not so easy. The feeling has to do with cut, length, fabrication...lots of things. I've bombed with a few attempts in previous seasons but this year I hit the bonanza. I had some that felt completely casual (like I might wear them on the beach), some that felt "going into town casual," and some that were more "casual occasion" oriented. Just saying, don't give up on the dress idea or perhaps the skirt/ top idea if dresses are hard to fit.