I too work at home for the most part but I just feel better when I wear something that is more put together than a sweatshirt and jeans. It's easy to get into a rut, but here are four classic outfits that I always know will work for me. Hopefully they will work for Erin too.
I love a striped tee on it's own with jeans and boots in winter/flats or sandals in summer, but I also love layering with a military inspired jacket like the one shown. This jacket would also go with plain shirts, or other embellished/printed shirts. Anthropologie has a lot of good ones - or Shop Ruche (although they sell out fast) is great for those on a tighter budget.
A plain black tee or sweater is a classic look - again with jeans (any kind), a skirt in the spring (or paired with a skirt/tights in the winter/fall). You can mix up the footwear with boots as shown, pumps, flats, whatever you prefer. I picked a leopard scarf because leopard is classic (in my opinion) but any printed scarf would pop against a plain top (and this goes for any color top, not just black).
This blazer is almost sold out online but it's a great example of a classic, yet unique jacket. I love jackets like this because they make any outfit look instantly polished - even with just a plain tshirt or tank underneath.
Take any pretty top (patterned or embellished) and throw a longish fitted cardigan like this one from J Crew over it. The shirt is great on it's own in warmer weather but the cardigan adds a warm layer for fall and winter. You could also change out the boots for flats if you prefer - or maybe wedge sandals in the warm months.