I still would like to see some photos of a person wearing what you DO like OP!!! Or a description. Who/what appeals to you when you look at other women??? Your height and weight indicate that your figure is quite decent! 
The one thing I would add is that as a woman in her late 40’s I know what I like and am comfortable in. If I find something I love–pants, shirts, shoes–I often buy multiples and often duplicates of the same color I wear most. I have 4 pairs of the same jeans, 3 of the same cardigan, for example. I loved the electric blue of this year, but for all I know next year will be peaches and mauves again and I’m not going there.
abasket - what a great idea to have LasMa post some links of styles and looks that she likes. LasMa???
I find going into Kohl’s overwhelming. So much stuff on the racks, so many sales. Makes me more likely to walk out with stuff I don’t like by the time I get home. I’m one who can’t wear the wraparound dresses that many others here love. Doesn’t work on my body type. (5’8", 32.5" inseam, apple-shaped, skinny legs, size 12-14 on top and hips, size 16-18 waist, depending on the cut). NYDJ jeans were not for me – too high-waisted. Kohl’s Sonoma house brand are perfect – midrise, straight hip and legs.
LLBean carries medium tall and tall pants. I’ve found that Dress Barn’s dresses work really well for me and are reasonably priced.
I’d wear a pair of pants and whatever jewelry you usually wear (big pieces? small ones?) you love to the store and just focus on shirts. A good shirt/blouse should frame your face, enhance your coloring and NOT make you want to pull at it all day. <---- this is why I don’t wear collars much any more.
You might start with the kind of clothes you find yourself wearing most, even if you plan to replace them.
I am probably not the best one to get advice from, since my wardrobe mostly comes from REI and I wear things way past their pull date, but if you think about the kind of outfits youve had over the years, you may be able to identify a theme.
For instance, I like denim. I like jeans, and denim skirts & jackets. I don’t wear more than one piece at a time, but I like mixing textures. I like wearing a fitted jean jacket with a floral full skirted dress, or a striped tee & denim sheath skirt & no collar wool crepe jacket, but I dont like pants so mch. Ive worn the same kind of stuff all my life, except for an unfortunate phase in the 70’s when I was in high school.
Im pretty short waisted with narrow hips, but not much waist. Narrow shoulders as well, so definitely apple tendencies.
When padded shoulders and dolman sleeves were in, I had a great Norma Kamali sweatshirt dress that was so comfortable and cute! I don’t really need huge shoulder pads to come back ( although at the time, they did balance out the boobs) but I wouldn’t pass up a little more shaping.
My new favorite shirt is actually one I got for my husband at Jcrew last year. Its cotton chambray tattersall plaid but almost gauzy, although it has facing or something so it seems to be made better than some of the women clothes.
I wear it unbuttoned, and the sleeves rolled a little over a tank top. So far he hasn’t asked for it back!
My feet suck, so I don’t wear heels, but in the fall/winter, I wear boots a lot. Very comfortable, they keep your legs warm and your feet dry. Boots are one of the best things about fall.
You may have a favorite sweater that youve tried to replicate or a color you really like. What color lipsticks do you think look good on you? pinks or corals?
I admit, it can be tricky to figure out colors.
I have strawberry blond hair which is supposed to be one thing, but blue eyes, which is something else. I just wear what I like.
I think you might have better luck if you can give what you want for your wardrobe a little thought before your next trip/ meet with a personal shopper. I used to look for certain brands to try on, which saved time.
I like the idea of finding a boutique, or asking someone whose look you admire where they go shopping.
My friends either wear the jjill mode of clothing, ( the older ones, how good they look depends on their body type. I have one friend who is probably in her early 70’s and she is easily as striking as Helen Mirren, if not more so, since her coloring is a little darker. Has mostly white hair, but still dark eye brows, and amazing eyes and bone structure). But if you are rounder, unstructured clothing, just makes you look dumpy,especially if you are shorter, if you don’t have strong jewelry or maybe a shoulder line.
Remember Bea Arthur? She wore unstructured clothing, but she was tall and had strong features.
Then I have friends who are perhaps in their 30s , and I am amazed at how dumpy they look.
Admittedly, when I was that age, I was wearing Laura Ashley, so I really can’t criticize!!!
LaMas if it isn’t comfortable on you, then it’s not.
For instance, I’m not a skirt or dress fan either. No reason why, I don’t feel comfortable in a skirt and hardly ever wear them. I have cute flats but usually wear sensible comfortable shoes. I figure that I’m old enough to know what I want to wear now and uncomfortable clothes and shoes aren’t it. I think people look great in Eileen Fisher but it’s not my look. Again, I have come to the conclusion that I am going to wear what fits me.
I haven’t read all the replies, so sorry if this was already mentioned. Know what colors look best on you.
The way I narrow down my choices to by eliminating all items that are in colors that don’t look good on me. This helps me to quickly narrow down my options.
If you don’t have a friend who is ‘good with color’ then this website may be helpful to you: http://www.colormepretty.co/categories-2/4-season-color-analysis/
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I still would like to see some photos of a person wearing what you DO like OP!!! Or a description. Who/what appeals to you when you look at other women???
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What a good idea! Will post some links this evening. Thanks.
And thanks to everyone. This is so helpful and encouraging.
Ok, I went through the majority of the earlier posts. Completely agree that a personal shopper is the way to go to get started. Or a friend with a good eye for style.
When I go shopping, I wear outfits that are super easy to put on and take off (and no makeup to mess things up), so the dressing game is easier to play. Sales people at nicer stores would be happy to fetch you another size or bring a coordinating piece or suggest another item. The trade off, of course, is the higher prices.
Another piece of advice: if you find a brand or two you like, stick with it. It will be much easier to coordinate things, and the sizing/fit will be familiar. When you figure out what works for you, shopping becomes easier. I personally gravitate towards Boss, Nordstrom’s Ckassiques, and Max Mara and learned to bookmark what I like to get it on sale later. For “play clothes,” I like Vince’s slouchy sweaters/jeans and Tommy Bahama dresses. If an outfit is taking longer than 2-3 minutes to put on, it is not worth having it in my wardrobe (the exception is evening dresses).
Deb, you said you are petite. I am too, so EF doesn’t work.
My work uniform is black, navy, and occasional brown pants. I buy pretty shirts, and have a collection of cardigans.
When you find pants that fit you well, get 3 colors. Do the same with cardigans. I also have silk shells in various colors. My splurge will be an Elle tahari blouse, which are colorful and are as dressy as I need for holiday parties. I’ll ask them to let me know when “my shirt” goes on sale.
Anyway, we all wish you luck in finding your basic look. After that, you can be more adventurous. (I got a pair of jeans at anthropologist that are gray/white gingham, for fun).
Two fashion-savvy co-workers have just informed me that my style is “classic”, “timeless,” and “conservative.”
I had a somewhat similar problem, but I am working on it. Lots of good advice on this thread, so I only have few things to add. Try to find your ideal look online (pinterest is a good place to start). If you could bring these pictures to your first session with a personal shopper, this would make the meeting more productive.
When you go shopping, make sure that you are in good mood, well-rested, have plenty of time, not starving etc. It’s very difficult to make good choices while absent minded.
Sticking with a brand / designer that suits your style and body type is a very good advice, and it would make your shopping experience much easier. Based on your style and body type, you may want to try Elie Tahari.
Elle tahari is expensive. The gorgeous silk blouses I admire are $280, but on sale $100"or more off. Then again, I’ve never tried their pants, etc.
I’m reinforcing the personal shopper at Nordies or Bloomies.
^^^ Very true, but we have Elie Tahari premium outlet nearby, and they have great selection and prices. I also find great ET pieces at my local Lord & Taylor store, and they have huge sale several times a year.
If you have a classic, traditional style and prefer to wear pants rather than dresses, an easy uniform concept is black, navy or charcoal slim, straight-legged, flat-front trousers in a wool with a slight stretch; a sleeveless knit or jersey top worn untucked; and some kind of jacket or jacket equivalent.
Variations on the top could be a basic tank, a draped cowl-necked style, some sort of knotted detail, etc. Ruched or not ruched on the sides. Further variation could be in solid or print. If solid with a simple neckline, a bold necklace could be added.
Jackets could be blazers, moto-style, cardigans or boxy lapel-less Chanel/ St. john style. Cardigans can be further broken down into classic, tailored or flowy. Blazers could be hip length or longer; garbardine or knit tweed, etc.
The fussier the jacket, the plainer the top, and vice versa.
One way to figure out the styles that look good out of these choices is to wear a plain black pair of trousers and a black or white tank and then try on multiple examples in each category one after another.
I find having a mental taxonomy that I’m constantly refining in my head helps me to keep from becoming overwhelmed by all the choices. And you can see right away how small differences change whether a look is flattering or not.
Many on this site will probably think that this approach will lead to a boring wardrobe, but it is an easy way to look reasonably up to date (although, unfortunately, skirts and dresses seem to be way more in style right now than pants).
^^restraint = elegance
imho
OP, I’m with you some how I don’t like shopping any more. Even trying for clothes, i didn’t try at the shop. Too lazy. If it’s cheaper than$10, I just grab it, sometimes there are too too short or to big, like 2 sizes too big. Oh well. It’s not worth a bother.
Oops posted too soon.
Well, it helps to see some pics! (they may not stay up though - hope some others see them while they are up!!!
That is really helpful, @nottelling , the taxonomy approach. I need to think about this analytically, not artistically. A formula of some kind. Tips like this are pure gold:
So in talking with you all and my co-workers and thinking about this all day, I think I’m actually sort of satisfied with the idea behind my basic work look – classic trousers in neutral (yep, black/charcoal/navy are my neutrals), and a nicer shirt. And I need to give some thought to “completer” pieces and accessories, because I can see that that’s what makes an outfit look put-together and polished. I don’t think I need to change my look, just boost it 3 or 4 notches, add some interest or pop – without going crazy, and while remaining age-appropriate. So not a change of direction, just a branching out. That seems more manageable to me.
Thanks for this assignment, @abasket. I’ve learned some things about what I like. For example, I like clean un-fussy lines, and while I like color, even bright color, I don’t like it in large doses
I would wear this outfit exactly as it is except for the heels. http://women-outfits.com/2015/03/29/6-professional-work-outfits-on-a-budget/
Let’s assume this girl is wearing a bootcut trouser. What I like about the blazer is that it’s slim and short. And the wild print blouse isn’t too much because you don’t see a lot of it. http://corporette.com/2010/04/15/emergency-reader-mail-what-to-wear-to-a-conference/
I like the curve of the sweater bottom – makes it interesting – and the whole outfit looks smooth and clean. Wearing statement jewelry is something I’d like to learn to do. http://www.outfitposts.com/2013/11/outfit-post-burgundymaroon-cardigan.html#.VcF9YbvbKUk
Do I like this? I’m not sure. It’s a definitely a departure. Maybe this is a date-night shirt (which I also need). http://www1.bloomingdales.com/shop/product/boss-imoree-flower-print-tie-dye-blouse?ID=637366&CategoryID=10527&LinkType=#fn=spp=8&ppp=96&sp=7&rid=28&spc=712
Fun because of the print, not scary because of the color. http://www.bloglovin.com/blogs/outfit-posts-3889345?post=1540819211&group=0&frame_type=a&context=post_page&context_ids=&blog=3889345&frame=1&click=0&user=0&viewer=true
ALSO! I signed up with Stitch Fix, and my first shipment is coming next week! For the first box, I asked for mostly work shirts, maybe a work trou. Those of you who’ve posted here that you’re fashion-challenged, I’d encourage you to take a look. It’s a good website, very user-friendly, and they walk you through creating your profile. It was so easy that even fashion-challenged me didn’t need my D’s help.