Also check Costco- I recently picked up a pair of black Calvin Klein pants that are in between jeans and slacks. They were cheap and I think they will come in handy this fall and winter.
It might also be helpful to know where you like your waistline on oants to fit. And do you like a baggy leg or would you prefer a skinny leg. Don’t be afraid to try on a slender leg. It can be very flattering.
My SIL and her sister used Stitchfix. SIL kept everything thy sent but one sweater. Her sister didn’t have good luck on the first shipment (didn’t fit right but she loved the styles chosen)…but scored very well on the second shipment. Both said it was fun to see what stitchfix sent them. Both were happy with the selections.
I absolutely would hate shopping for a whole new wardrobe. I buy things I like as I see them. A short her. Shoes there. A dress someplace else. I do NOT go out on exclusively clothing shopping trips…at all.
As nottelling suggests, I’ve recently adopted a “uniform” and it makes dressing so much easier. After watching a couple episodes of “New Girl” with Zooey Deschanel, I found her style to be timeless and classic. Essentially it is a dress with a cardigan. It is also seasonless because the outfits can be worn with sandals/flats in the warm months and boots during the cold ones. I was searching to find some sample outfits only to discover that the “Jess Day” look is a thing. If you adjust for dress length, I think that the look is appropriate for any age. Plus, it is more economical to buy a dress, than to buy separates; sometimes tops cost more than dresses and the right fitting pants can get really expensive.
@LasMa:
Without reading all the posts, I think I can sort of answer what’s between your work uniform (nice pants, button-down shirt) and your casual uniform (jeans, polo). There are “dressy jeans” (velvet or colors like purple, red, etc.). You can wear a nice blouse or a pretty sweater with your regular jeans, too.
I have a uniform myself, and it’s quite similar to yours: black pants (in different weights, textures, fits, depending on the circumstances–I like Lucy and Icebreaker). In the summer, I wear Prana t-shirts, which come in all sorts of pretty designs and colors. In the winter, I wear a lightweight wool t-shirt (Icebreaker) under a cashmere sweater. (I have wool itch but cashmere is okay.) I have the same cashmere sweater in (literally) ten different colors. I wear earrings in colors that coordinate or contrast with the sweater or t-shirt.
When I want to “dress up,” I wear better black pants and a silk shirt.
Since I hit a “certain age” and got tired of having sore feet, I always wear “sneakers”–but I look hard for good-looking ones. After three years of no dress shoes ever, my bunions have almost completely reversed themselves and my feet almost never hurt.
Living in Portland, OR makes it possible–in other parts of the country, black pants, silk shirt, and sneakers would be considered casual!
Edited to add: when you’re trying on clothes, hand your phone to the sales person and ask her to take a quick video while you turn around twice. It’s MUCH better than looking in the mirror.
I’m with OP on hating shopping. When I was a younger adult, I hated it because it was so difficult to find things sized for petites. As I’ve gotten older, I still hate it even though there are more petite items. There’s no consistency in sizing betweeen brands, and sometimes within a brand. It’s very frustrating.
I’m much less averse than I used to be to ordering clothes online, especially with stores like Nordstrom that have free shipping and returns.
I’d never heard of Stitchfix before, so I’ll check that out too. I mainly shop when I absolutely need something, but that’s not always a very efficient or fruitful way to shop. It would be nicer to have things in my closet that would be suitable for various occasions.
Here is my suggestion. Go through your closet, and choose some selected items that you like, and wear and can be used to build a newer wardrobe. Keep those things. Toss the rest.
Don’t try to replace your entire wardrobe in one clothing shopping trip. Even with a personal,shopper, that won’t be fun if you don’t like shopping. Go out and look for selected things. You might want to look for,some new tops to go with slacks you already have. Next trip…look for some new slacks (and get rid of any old ones you are replacing). Next time, go for shoes. You have the picture. You might see other things you like while out…fine…get those too.
Go,with a friend and include lunch in the outing. Plan to go in the morning…and be done in time for lunch. A couple of hours of clothing shopping is quite enough for someone who doesn’t like shopping.
Coming late to the discussion… I will add a couple of thoughts, but I have to go through all posts so there would be no duplication of what has been suggested so far.
I have to say that shopping is not among my hobbies, but I learned how to do it efficiently to maximize the return on the invested time.
I’m a do-it-all-in-one-trip kind of shopper. I like to have the three way mirrors to see what entire outfits look like and like to be able to coordinate entire outfits, and like to be able to see what mixes and matches. I really don’t like shopping and would rather go once a year and get it all done (except for bathing suits or summer stuff which requires its own day from hell). If I try to pick up pieces here and there I never feel good in them and never wear them. I always end up wearing the stuff I buy on my mammoth shopping days the most.
Based on your posts, I think you need to start with a personal shopper and perhaps move to stitchwitz once you figure out your style.
It seems like you don’t have a real idea what you want your “look” to be. That is the very first step, imho. There are many excellent looks, but you need to determine the one that suits your lifestyle and makes you happy. A good personal shopper can help you accomplish this. It may be a huge try-on day, but once you have decided on the look, everything will get easier. Then you should have pictures in your mind about what will work with what you already have in your closet. And you can just not even look at 95% of what you see on the racks or on-line because they aren’t part of your look. If you invest the time to figure it out, I think all your clothes selection will get much simpler. jmho.
I wear dresses with comfortable shoes. I think I look okay, or anyway it works for me. Again, it takes some searching. There are other shoe choices than those you mentioned. If you want to wear dresses and skirts, I don’t think you have to be limited by feet issues.
Good luck!! 
@alh The reason I’m not considering dresses/skirts is because I have to wear this kind of shoe, which I just can’t see with a dress. My shoes have to be substantial and well-made. They must enclose the entire foot, and must be roomy enough to hold both my tall high-arch foot and a fairly bulky orthotic. Heels are off-limits. When I think dress, I think either business-y pump, or else strappy sandal/ballet flat, none of which is an option for me, doctors orders. But these are good with pants; they look like a boot and I do like that look.
I wear longer dresses that would work with that shoe. I don’t think I would care for them with Bunsen’s beautiful wrap dresses, but maybe it would be possible to style it somehow?
But none of that matters until you decide the style you like that works for you. If you want dresses and skirts and need a certain shoe, ask the personal shopper what is possible. You may be surprised. And you have nothing to lose. In my mind that would be one of the explorations you could do, if you were interested. Try on all the looks. Pick one out. Then you’re set. imho.
adding: to be honest, your current look sounds very attractive to me, but I can see how you may be bored if you’ve been wearing it for decades.
LasMa, I see no reason why these shoes could not be worn with black tights and a denim, tweed, or boucle skirt. Top it off with a shirt/sweater, and you have a nice business casual look.
BTW, oxfords look good with skirts or dresses, for example:
@alh That might be step 2. For now, I think I’m happy with pants, IF I can get some looks seem even a little better than what I’ve been wearing. Maybe then I’d feel comfortable to branch out. But baby steps.
Yikes, BB! That is super cute on her, but sooooooooo far outside my comfort zone that I’d feel like I was trying to be someone I’m not. I’m not even comfortable inside my own comfort zone. Well, actually, do you want to know what my comfort zone is? Men’s sweatpants and a t-shirt that’s a size too large. This is what you’re working with.
Pants are a good look.
I have to admit I think your choice of shoes is problematic with a lot stylish clothes. Ok for wearing with cute pair of skilly jeans and casual top (big sweater, long tee, etc.) I have terrible feet and wear orthodontics - but only with my sneakers - which I put on after I come home from where ever I have been. I a;so make sure I wear them around the house, when I am puttering in the garden, taking dogs out for walks and when I am in athletic wear - otherwise I wear a shoe which goes well with the style of clothes I am wearing.
I love your letter.
And, honestly, I didn’t know how to shop either until my D became a teenager and began saying things like, “Now Mom, you’re not going out dressed like that, are you?”
My saving grace was consignment/thrift stores…a smaller selection and also much less pressure. My back-up plan is Eileen Fisher…only issue there is that it’s pricey so I have to tread carefully…
EB…some people don’t have the choice you have about orthotics…they have to wear them…period. My SIL is one of them. She has a nice wardrobe of boots…and they are stylish and look good. She has some nicer shoes, but really can only wear them for an hour or two…at the most.
@LasMa ok…start with the personal,shopper…who at least can get you started with a style you like…and a color palette.
53 - Are you more comfortable in loose rather than tailored clothes? Because that is a "look" :)Th
My sister prefers pants with a very tailored, fitted look. There are other ways to wear pants.
https://newyork.oska.com/en/outfits/detail/look-b/
?? don’t look at the prices, just the style
adding: I still think you need the stylist but this is fun for me to talk and think about. IRL, I’m working on figuring out my fall/winter wardrobe choices. So I have clothes on my brain even more than usual.
"some people don’t have the choice you have about orthotics…they have to wear them…period. "
Which is what my podiatrist said I had to do also. But I don’t because I don’t want to wear ugly shoes with my nice clothes.