My HG of weekend wear is Lands End. I like my weekend clothes to be comfortable, slightly less refined than work wear, cheap, and able to withstand frequent washing. Enter the regular original shaped (having challenges naming your fits, much?) 1x1 rib top. Crew neck, v-neck, short sleeved, long sleeved -- I have them all in many colors.
And when I'm feeling sporty, the pima polo:
It's less bag-like in person. Last year it had a little strip of polka-dotted grosgrain ribbon around the interior of the collar, but not this year. What the hell, LE?
Both of these styles have held up great for the past year, despite frequent beatings. They're fitted enough so that it's obvious I'm a woman, but not so fitted as to give away the texture of my bra.
For fun summer polos (...as opposed to serious?), my favorite is Lilly Pulitzer.
They don't have the best shelf-life, but to be fair, I do wear them everywhere. I also like Etienne Aigner loafers, but they haven't proven themselves just yet for long-distance walking. In the winter I wear my Sudini boots mentioned in my work wear post.
Next up, handbags.
For pants, I like Land's End the cords in winter. I'm also a huge fan of the 7" old-lady shorts for summer. Last year they had some with 4 buttons down each side -- an embellishment that deludes me into thinking they look age-appropriate on a 26 year old. The higher rise makes your shirts lay flatter across the front AND prevents them from sagging. And in case you were worried about looking even a little sexy, don't worry, these have the added benefit of a little strip of elastic in back to ensure maximum Mom Jean effect.
But seriously, I freaking love those shorts. Just make sure your shirt is long enough to cover half of your butt, and you're golden.
Shoes. I'm sort of crazy about shoes. Not that I love them, just that I have incredibly high expectations, and that leads me to being UBER selective in what I'll even consider wearing. Since my main mode of transportation is my feet, I can't deal with anything remotely irritating or painful. L.L. Bean's Camden Driving Mocs are tight like a glove out of the box, but stretch to your foot within a couple hours.