Reddit mentions of Eastland Women's Newbury Penny Loafer, Black, 10 M US

I consider myself a bit of a clothes hound, and have been named 'best dressed teacher' three years in a row by the graduating senior classes. I really enjoy dressing up for work everyday, but I'm very cost conscious and work with a budget. My advice is to get a few quality pieces that will last with wear and carry you through a few years. This can be done cheaply, so long as you research materials, take good care of your clothing, and buy things that can work with multiple pieces.

• Cigarette pants - my staple wardrobe piece. I had several pairs in a few different colors (black, white, brown, grey, pink, cobalt, neon yellow). They dressed up very easily with heels, were really casual with flats, and paired well with a variety of tops. They held up well with several years of wear, as well. I highly recommend picking some up!
  
  
• Sheath dresses - conservative enough to wear to schools (especially if paired with a nice cardigan), but not as frumpy as a skirt/sweater combo. I had several of these, and they transitioned well from the classroom to after school events like dances, talent shows, recitals, ect. I recommend picking some up at TJ Maxx/Marshalls, or even Target. I've never spent more than $40 on one at those stores.
  
  
• Several textured blouses/tanks (example 1, example 2) - comfy, casual, but still on the dressier side. I lived in shirts like these. The sales rack at Banana Republic is great for finding cute and fashionable work shirts. They also offer a nice teacher discount on their regularly priced merchandise.
  
  
• Simple shirts from Marshalls, TJ Maxx, or Target - you can usually find durable, well made and cute shirts from these stores at very reasonable prices.
  
  
• Pencil skirts - pair with a nice blouse or a fitted cardigan.
  
  
• Shoes - black heels are brainless. A few pairs of flats are a good idea. I would avoid anything blocky or chunky, since those can up the frump factor really quickly. Look for sleekly cushioned shoes, or add inserts as necessary.
  
  General rule of thumb: to avoid looking frumpy, make sure your clothes look tailored to your frame (you don't have to actually tailor your clothes to achieve this). If you're wearing loose pants, wear a more fitted shirt, and vice versa. You don't want to be swimming in your clothing. I know you mentioned you have a curvy figure, so I appreciate your struggles (I'm large busted myself); don't be afraid of your figure - it's likely hard to cover it up without making yourself look like a grandma. Be comfortable, but don't drown yourself in fabric, either. You don't want curtain boob.