If you haven't been in an office setting in 15 years, it's gotten a whole lot more casual! You might not need formal work outfits.

Part of the problem is that you got used to really soft clothing, and tailored clothes will be more constricting by definition - you can't get away from that. I think you need to ask yourself whether you NEED these tailored pants? Can you have a nice blouse and an A-line skirt instead?

Personally, high waists are my friend, OP. They flatter my still small, high waist, and hide the marshmallow below. I've always had sensitive feet. My max heel height is 2 inches and I absolutely need a round toe box. I've found plenty of cute styles with those criteria. None of those mean pointy shoes, or dagger stilettos!

Dresses are way more comfy than pants. I've had luck at Boden and Ann Taylor (though I'm taller and larger than you). Wedges or block heels are more comfortable than pumps and look a little nicer than flats, esp. with dresses (agree that something like Rothys are the answer if you only want flats).

Anonymous wrote:I understand the high heel issues. But is it about the old clothes you find uncomfortable? The fabrics? The cut is too figure revealing? It’s hard to respond without really understanding the problem.

I read your update and agree you need tailoring.

I'm in my 60's and stylish & comfortable and I work. Not sure about you.

Anonymous wrote:You will need to get jeans and trousers tailored, it sounds like.

This. For a professional setting, get your items tailored. I think it would be very much worth it.

I understand the high heel issues. But is it about the old clothes you find uncomfortable? The fabrics? The cut is too figure revealing? It’s hard to respond without really understanding the problem.

OP, what's your budget?

Some ideas below. All the websites linked have other options.

For shoes the simplest option would be Rothy's or Vivaia woven flats. Maybe not the absolute most stylish but nice enough, machine washable, and you don't need to wear with socks if you don't want. They are very comfortable. Vivaia in particular has a million options.

https://www.vivaia.com/item/pointed-toe-striped-flats-p_10003079.html?gid=10003092
https://www.vivaia.com/item/almond-toe-ballet-flats-tamia-2-0-p_10001532.html?gid=10001532
https://rothys.com/products/square-toe-mary-jane-black

Dresses are the easiest option
https://www.quince.com/women/linen-dress?color=deep-navy&tracker=collection_page__%2Fwomen%2Fdresses__Work+Dresses__10
https://www.cos.com/en-us/women/womenswear/dresses/mididresses/product/belted-short-sleeved-midi-shirt-dress-navy-1271953003
https://bananarepublic.gap.com/browse/product.do?pid=535705002&vid=1&pcid=69883&cid=69883&nav=meganav%3AWomen%3AWOMEN%27S+CLOTHING%3ADresses+%26+Jumpsuits#pdp-page-content

You will need to get jeans and trousers tailored, it sounds like.

These are my favorite work pants:

https://www.anthropologie.com/shop/the-colette-full-length-wide-leg-pants-by-maeve?category=SEARCHRESULTS&color=029&searchparams=q=collette%2520pants&type=STANDARD&quantity=1

OP here. I'm asking for examples! Please send me examples of business casual outfits that are comfortable. I haven't been in an office environment for 15 years so I'm totally at a loss here.

In my current life, I wear lots of leggings and joggers with cute tees or sweatshirts. I also like midi and maxi skirts and dresses if they are not constricting at all (looser fit, elastic waist, long enough that I will not need to worry sitting down or riding a bike).

I went to try on work pants recently at a few stores (Madewell, Nordstrom, Loft, etc.) and was frustrated both by how they felt and how hard it was to find flattering pants for my late-40s body. When I sized up to a comfortable waist size, they just felt frumpy and voluminous. I don't have a huge waist, I'm a relatively small person, but I used to consistently wear a size 0 in pants and now it's more like a size 4, which just looks huge on my small frame.

Yes but you need to spend a day shopping in person. Go to Tysons or another big mall/shopping center with a mix of stores. Try on a ton of clothes and shoes. Buy what you like and keep notes on your phone of what you don't like or what sizes don't fit correctly for particular brands so you don't waste time on them in the future.

It's absolutely possible to be stylish and comfortable.

OP, what type of office do you work in? Are you a dress person, a pants person, or both? Do you prefer to dress in colors or neutrals? Give us something to work with here....

It is for me; might not be possible for you.

Seriously? Of course it is. I get that menopause can make dressing a lot tougher, but in your 40s why would you have any issues dressing comfortably and stylish?

If so... how? Real question.

I am starting to shop for a return to the office and I'd like a uniform of sorts that is stylish, flattering, and comfortable. No heels. No constricting or fussy clothing items. Soft fabrics that feel good on the skin.

I wear a size 2/4 but have some roundness in my belly now that I'd love to conceal. What do I wear? How do I shop? I don't want to look like I've given up but I can't go back to dressing like I did the last time I was in the office because it would be too uncomfortable now.