I wear flats with skirts and dresses all the time. I'm not going to put myself in pain and ruin my feet. Heels hurt. F that.

I find that I look and feel more professional when I wear a blazer, even though my office is business casual. It just looks more pulled together. Not sure of your size OP, but I'm on the heavier end of normal (not quite overweight but bordering on it) and I think the cardigans make me look chunkier/forum pier. Plus, my female bosses (I am middle management too) usually wear them. Try Marshall's or Ross.

Re: shoes - id invest in a couple of pairs of nice flats. I think you can wear them with skirts

I'm similar to OP, but yeah, I also spend about $250 per year on clothes, so a $500 blazer isn't going to happen! Wow.

shoes: Shoes really do make a difference. I do think it is worthwhile to try a lot of different brands to find some that work for your feet. I can go up to 2.75", but there are some really good looking and professional kitten heels around. Too round of a toe will look stumpy and/or casual, so look for a more almond to slightly pointy toe. My preferred brands, which may or may not work for you as we are all different: Cole Haan with Nike, Rockport with Adidas, Sofft, Calvin Klein, Coach, Clarks (Privo or Artisans line), Ecco, Born.

Sounds like you have a good assortment of basic bottoms. Instead of cardigans, look for some interesting tops in patterns. Banana Republic, Old Navy, Target, Boden.

Accessorize. This blog post is pretty good:
http://www.bridgetteraes.com/2014/03/30/how-to-look-stylish/

A few inexpensive necklaces and a few scarves can definitely punch up your wardrobe.

Also if your skirt is just above the knee you can wear flats but I find it looks a little more casual unless you are very tall or your flats are pointy.

I am middle mgmt, 38 yrs old, my normal go to work clothes are as follows:

Pencil skirt- cardigan or tucked in blouse with nice jewelry or scarf. Heels and yes, you can do a Mary Jane strap on a nice shoe ( avoid platform)

Wrap dress with above mentioned accessories

Skinny pants with nice blouse, sometimes cardigan. Low heels.

I wear dresses and skirts most of the time because they require the least amount of thought. Sheath dresses are very useful and also modest.

Get yourself some decent accessories, some pencil skirts and nice shoes.

I can't figure out how to post the pics. Just search for Mary Jane mid-heels. You can even look for wide. It may take some browsing to find ones that aren't old lady looking and aren't $800 Prada pumps but trust me they're out there. Try Polyvore or shopstyle.

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I spend about $250/month. I think per year is extreme.

Anonymous wrote:Talbots, brooks brothers, neimans on sale, Saks on sale. I'd spend $500 on a really nice blazer or other workhorse piece that's beatifully cut. Or some high quality jewelry.

LMAO! Sorry, I'm just passing through and this make me literally laugh out loud (after reading a second time to make sure I didn't mis-read). I spend about $200-250 per YEAR on clothing/shoes. I hope the person suggesting things like this isn't also the OP of threads like "We bring in $250,000 a year but are broke!"

OP here, on heels: the height, the way they squish my toes and rub my heel. I get just awful blisters. Also I'm not so coordinated. 2 inches is my limit, if cushioned and a chunky or wedge heel. Mary-Jane straps help and I love that style but it doesn't seem very professional. The shoe thing is, in fact, what keeps me from doing pencil skirts more often.

Pencil skirt and blouse. What part of pumps make them uncomfortable? Height or width? I find 2 inch pumps more comfortable than flats.

Dresses. Lots of beautiful, well tailored dresses.

Talbots, brooks brothers, neimans on sale, Saks on sale. I'd spend $500 on a really nice blazer or other workhorse piece that's beatifully cut. Or some high quality jewelry.

I'm looking to refresh my wardrobe and make it a little more professional. I don't need suits, but would like something nicer than pants and a cardigan, if that's possible. My male colleagues wear nice pants, dress shirts and ties, though not jackets. I'm 40 years old. Also, I can't wear pumps because they kill my feet. Any hope out there for me?