I stumbled on this Casual Affordable Winter Clothing article by Yolanda Wikiel on Real Simple's website. Although all of the offerings are under $100, I don't think they are all worth it.
One of the disappointing items she featured is this faux fur trapper hat for $70.
I can't see a savvy person spending $70 for a trendy hat that will likely only be worn a handful of times.
Instead, I would rather spend $89.50 on this beautiful wool dress she featured from The Loft. The classic look can be worn for business meetings, speaking engagements and holiday events.
In fact, I bookmarked the dress on Loft.com and will check back over the next few weeks to see if it is going to go on sale. It's worth $89.50, but if I can get it for less, that's even better!