Hah, Tracina - so true! This is me half the time. (I also did the 3x a day change out when young.)

I have always had a great sense of style...for others --and myself in my head. I'm the friend that goes shopping, will style my friends and leave with nothing because NOTHING ever fits me right. You know "right". Right as in how you see it in the magazines, on TV and on people who are shaped completely different from us.

Then, there's the fact that in my head, something will look wonderful, and the execution just never works out because either I get cold feet to wear something bold or just plain talk myself out of it because it's not "right". I have so many things that I've curated and finally purchased over the years because they are versatile...but I'm still coming out of my shell to get the mileage out of my wares.

I'm at a point now where I am have come to the conclusion that my fit issues have BEEN my fit issues since I was the magical "small". Even when I was tiny (and didn't know it), I had the EXACT same gripes as I have right now. Pants gap in the back, too much butt for fashions I like, thighs don't fit most denim cuts without stretch, too busty for shirts I like, can't wear button ups, must be careful about not sexying up normal clothes because things tend to fit snug when they fit "correctly". Those problems are STILL my problems, they will always be my problems, so I just need to get over it, and wear what I like and find a way to make them work for me.

I'll never get to where I have everything I need in my wardrobe, I love clothes, and love bags even more. What I hope is that I get to the point where my wardrobe is full of ONLY things that make me look and feel good -- because I went through a frumpy phase after my son 8 years ago. I'm talking CROCS in multiple colors ladies! :). It's easy to fall back into, if I keep those things at home. I'm trying to rid my wardrobe of things I don't look fantastic in. That's my goal - more than shopping for new things constantly is to pare down what I have to a small and fab wardrobe --adding things as necessary.

So many great answers here. More disposable income would certainly help, and I'm still learning who I am style-wise. This is a great question, thanks!

Mostly the money. Wich isn't always bad because I'm not making costly mistakes as quickly, but my style is definitely not as defined as it could already be because of the budget.

For years I didn't realize that fashion and style are intellectual exercises, that there is indeed a thought-provoking comittment to fashion and it isn't just randomly pulling items from the closet and hoping for the best! I think I thought fashion was a frivolous endeavor and I was above all that. And then I discovered YLF and my thinking changed dramatically. I was in awe of the beautiful ensembles Angie (and the lovely ladies of the forum) put together and the components that made up those lovely ensembles. I have learned so much in the years I have been consulting YLF. I am much more discriminating in the assembling of my outfits and I think (hope . . .) that my style demonstrates this. And it's been so much fun!

I just buy what fits, that I love. Maybe it doesn't fit everyone else's
idea of Bohemian Rockstar Lumberjack, but I see it, and that's what
matters to me.

Ah, I remember those days. But, as others have pointed out, so many other factors--aging, health, budgets, shifting roles, job demands, fantasizing about a different life, uncertainty about dressing a different body shape, limited shopping opportunities, lack of time--all conspire to muddy the waters.

Expressing ourselves through our clothes is obviously important to most of us, or we wouldn't be on this forum, but the process is not the same for everyone, nor does it stay static. Bohemian Rockstar Lumberjack could have described me in my 20s, but would feel, and look, quite odd on me in my 60s. And I won't bore you with all the transformations that have gone on during my evolution to my current Elegant Urban Sophisticate. Just say that it has been mostly interesting, sometimes alarming, and not always painless.

I'm with Joni! I resisted fashion for a long time, as something superficial and kind of dumb. I've come to care about what I wear (in terms of how it looks, I've always been picky about fit and comfort) at a later age than some.

Some other things that are keeping me from my fashion aspirations:

1) Money, of course. I just bought a house with my fiancé. It's lovely but needs work. There goes a good chunk of disposable income. Also, as much as I've come to respect fashion, I have many other things I value more. So my finds need to be second-hand, thrift or consignment or otherwise mightily discounted.

2) Lack of focus. I have a lot of competing visions of what I want to look like, and what I like vs. what I like ON ME. They are slowly, slowly coming together.

Finding pieces in my style size fit and colors.

It's great to hear everyone's input on the subject! I love the variety of answers, but also how many are so similar

It seems that evolution of style is why so many aren't "there yet". I have to wonder, though: If we aren't there yet because our style is always evolving, will we ever "be there"? While I certainly don't feel as though I've reached the end of my fashion journey, I'm very pleased with my current rest stop Perhaps I go for a high happiness factor right now, as opposed to looking toward what my wardrobe could possibly evolve into. I don't know! I'm just rambling now

It's also fascinating to hear that some opted out of fashion, or didn't feel that it was an innate skill for them. I love hearing details of people's stories, and learning from them. Or maybe I'm just nosy

Thanks to all who've participated so far I can't wait to read more!

For me its been a journey in trying to find the "right" fit to flatter my body. I'm so unsure on what works and what doesn't. Also money has played a part but is not an issue now. I just need to learn more.

money

Because there are so many beautiful attractions to stop at along the way, because fashions ebbs and flows, because I can be a difficult to please moody bissum and because I fear i may find closet nirvana a little bit dull

Interesting! I appreciate what you just added about being pleased with the rest stop. Because really life is as they say a journey and not a destination. What I realize is that when I just bought whatever appealed to me while I was out shopping, I never had any true outfits or capsules that played well together. More an assortment of individual items with no cohesive look or feeling of "me". I also thought that style was just innate for some and I was baffled/daunted by how to get beyond jeans/tees/yoga pants!

So many reasons I'm not "there":
1. The way I looked in my head did not match what I saw in the mirror. I want the two images to match, and I had to learn how to do the work to do that.

2. Weight fluctuations. I've lost 2 sizes over the past year. At that point, nothing fits well. When/if I gain, the same will be true.

3. Practical limitations. I've waxed on endlessly about my moves, and I'm up against another one. Everything I need in the world must be less than 60 lbs. Clothes, shoes, toiletries, small sentimental things. When you only have room for 2 sweaters, you'd better love them.

4. Money--everyone's mentioned this one.

5. Perhaps the most important, and tying back into #1, is that I found that others didn't perceive me as I wished to be perceived. I need to "up my game" a little bit. More bluntly, I'm single (and have been for a while). The kinds of men I'd like to date and possibly get into a relationship with care about themselves and have at least a minimum amount of sense insofar as clothing fitting and being appropriate to the occasion in question. That person didn't pay attention to me when I looked like an overgrown college student (you can't wear jeans to everything).

For me, I think it has to do with stability. For the past 5 years I've never had a clear idea of where I will be or what I will be doing for more than a season or two, and haven't had a steady paycheck. It has made me reluctant to spend money on developing a wardrobe. Plus, I've been very busy in my personal life dealing with health, work, and death of family and friends. In the past 5 years, I've been diagnosed with a chronic illness, split with a fiance, dealt with spousal abuse, moved 9 times, went into heart failure (at age 21), graduated from college twice, became a grad student, worked many contract jobs, was a caretaker to a cancer patient, had 7 family members and 3 close friends die, found my SO and fell in love, etc.

December 11th will signal the start of me working full time for the same company. I hope to have money to spend on my wardrobe, as well as the time and stability to be able to make decisions about moving in with my SO, improving my health, painting and photographing for pleasure again, creating a happy wardrobe, and where I want to be working or going to school in the future.

Money again, by far. I am fairly confident in my style, both in what I like and what I need. It is just that the older I become, the more I crave quality, which comes with a pretty hefty price tag. Champagne taste, beer budget.

I've been reading some of these responses and it's interesting to see some YLFers who came onboard to learn how to dress (when I feel they're some of the most stylish women here in YLF). It's amazing how inspiring this community can be!

To answer your question, this us why I'm "not quite there yet"

1) Fit issues
I have a super short torso, undefined waist, busty, has a booty, with long limbs. If you combine all these factors together, you'll get all sorts of fit issues. Petite section jackets are fine on my torso but too short on the arms. Sheaths may fit well on the bust but are too loose on the hips.... You get the idea. Thus us why I have a trusted tailor.

2) My designer training
I'm visually sensitive. That means, I'm irritated when proportions are off on my outfits and when there's no harmonious visual balance. And with a non-modelesque body type like mine, I encounter this on a regular basis.

3) Comfort VS Aesthetics
My blog is named "Pretty Comfy" because I always find ways to make anything comfortable quite stylish. I don't like compromising either one because I just won't feel good about myself. That said, I'm limited to certain brands of footwear (NAOTs fit my comfort requirements and style quite well), prefer natural fibres and do not tend to wear anything that restricts my torso area (such as belts, though I wear long-line hosiery when wearing dresses because I don't like them digging into my torso).

4) Money
I find natural fibres to be pricey (but worth it) and NAOT shoes are quite expensive ($200+ a pair). So usually, I have to hold out until I can afford them.

5) My super slow career transition
I currently work in marketing where we are allowed a casual work environment. The career I'm transitioning to (counselling/facilitation/training) has a business casual work environment. For now, I'm not developing any new wardrobe sets, but when there time comes that I need to start volunteering and doing internships (next year), I'll need to have a solid business casual capsule. I haven't quite established my personal style in business casual mode.

I'm getting there, but I'm having trouble finding what I need in my price range. I have become increasingly picky about quality and refinement, and I won't settle for non-breathable/synthetics anymore. Also, I've seen what really good fit looks like, and I'm unwilling to compromise on that either. As a result, I have a very small wardrobe, but that works for my lifestyle.

I like the fact that this is all a journey, and even if I ever arrive at what I think I'm aiming for, I'm sure my style will evolve a little more, and I'll have something new to reach for. That's part of the fun!

This may be one of my favorite all time threads. Thank you !

There is so much to this question ( for me any way ) and so many great answers already. I completely lost any sense of style twice as an adult. When I became a stay at home mom and stopped working and traveling and moved to the country from a city and when I gained 30 something pounds as a result of meds.

Joy's statement of discipline really hit home. Discipline is tough for me because my aspirations don't fit my real life. And I am not good at translating "inspiration" into a real outfit. I am getting better at that. The exercise last year where Bella put up paintings and women interpreted them in their outfits ( and explained their thinking process ) was a real eye opener for me.

I also was very confused by magazines. I am almost embarrassed to admit it. I would see all these women in Vogue in gowns with wellies and pulling carrots out of the ground. I LOVE it !!! But it took me a while to realize it didn't work in real life. And that the magazines are about fantasy. Though that has changed over the years.

Money of course is always an issue but even if it weren't , it wouldn't make sense to dress in DVF silk dresses and jewels from H.Stern. Sometimes that makes me sad...the clothes...not the life. Because I wouldn't want to be DVF. I don't have the energy. : )

Competing goals, desires, and requirements. Also, a big move in from the suburbs to the gritty city. I'm a business writer by day, a bread baker by night, a preppy by blood tribe, and punk-ish by personality tribe.

And finally, I must always be prepared to walk the dog

I just thought of my REAL reason. I don't have the money to fly to Seattle and hire Angie and to buy all her choices for me. That would be the quickest and best way to get to where I want to be style wise.

LMAO. I am with MaryK all the way!

Hmmm interesting question!
Three things standing between where I am and where I want to be...
1. I've got a lot more to learn.
2. I've got a limited budget for clothes, shoes, and accessories.
3. I've got to gain about twelve pounds to reach what I consider an ideal weight for my body type.

Many of the above-stated reasons, except that instead of having a fantasy life, I'm perhaps too pragmatic about my present lifestyle not matching my former clothing style, and not knowing how to find middle ground. There's a lot of material there.

Money isn't unlimited, but since I want only *one* coat, *one* bag, and so on, these items have to be perfect and can cost a pretty chunk of change. Perhaps perfect minimalism *is* my fantasy.

I think I am there now but it does not mean I want to stay there forever because the best thing about style is its evolution: the journey is more important than the destination

I think I tend to play it too safe, combined with not having access to as many B&M stores to try things on now that I have some idea of how i need to juxtapose classic or safe with something more interesting. Plus so many things that look fun don't seem to fit me or look right when I try them on. So I buy more of what's available that seems to fitand don't break free of the stratosphere. I've had what I thought were some good " visions" of items, shoes, outfits of what i thought would be a good move for me, and then have not been able to find them, unless its that I still don't recognize it when I see it.

There are a few reasons for me:
-- I don't really know what it is that I want yet,
-- my aspirational tastes don't match my actual lifestyle,
-- I'm still hunting for a job and have a very tiny budget,
-- I'm too fat for most "regular" clothing and so it is difficult to find things that fit, let alone things that are flattering, in nice fabrics, and in my budget.

My size is the biggest problem. For whatever reason the clothing choices for the relatively tall plus size woman are pretty dire and overpriced around where I live, so even if I have an idea in mind of what I want it can be impossible to find.

Wow, I missed this thread! For me it's a job change. I WAS there, feeling consistent, confident and happy with a more honed UWP style with some androgynous looks thrown in there, even as a working MOTG. Having to dress more conservatively most of the time is really putting me off.

I missed this thread too, but it's such a good question, thought I'd chime in. For me, it's overcomplicating the issue. My style is simple, casual, classic, but I keep thinking I "should" be more fashion-forward, dressy, etc. So I go off-track and then end up having to purge some great items that just aren't me. Getting better though at just being me - approaching 40, so about time methinks!!!

I would say I am pretty much where I want to be stylewise, however the challenge is budget and availability of what I like. If I could afford a wardrobe of Rick Owens and Complex Geometries I would be a happy woman Finding the items that I love at my price point is challenging.