NWR: Help Me Shop for Winter Dresses

One of the issues with being a reformed wasteful spender is that I still have moments of wantwantwantmustbuyEVERYTHINGnow.  Today, one of those moments hit.  Fortunately, I am a reformed wasteful spender, so I'm trying to edit down my desires into something reasonable that meets my actual needs.  I "need/have been planning to buy" dresses for the following occasions:

• Thanksgiving at J's family home in Houston.  It's not formal and it's not jeans, so I'd like a versatile nice-but-casual vibe.
• Work-appropriate holiday party outfit.  This outfit will do double-duty at my family's holiday party too.  It needs to be festive but relatively demure and also have post-holiday utility. 
• J and my holiday party.  This should be neither fancy nor demure.  I'm going for generally awesome and re-wearable. 
• General winter wardrobe.  I prefer that my outfits do double duty for work and play, if at all possible.  I've been looking for sweater dresses/belted sweaters this year in brick-and-mortar stores without much luck. 
  

Unfortunately, I fell in love with far too many options at ModCloth and I need your editing assistance.  (At least I fell in love with something, since last weekend's mall shopping trip was a complete bust.) Let's also keep in mind that I'm still working on defining a reasonable personal style, so I very much appreciate outside opinions, especially from a blogosphere that's significantly more stylish than I am.  So help me, please, with selecting four outfits.  

This could be post-Thanksgiving appropriate, work appropriate and winter casual appropriate, right? I'm thinking I can style it with belts, tights, jeans, cute pumps or boots for full versatility. 

It's a skirt and a top (already versatile).  With a blazer and pumps I could absolutely wear this to work.  With cute flats this could be great for casual around-town.  Could it also work for Thanksgiving?  If so, how?

Work-appropriate, obviously.  It's not versatile at all, but it's definitely client-appropriate.  I'm trying to figure out what sort of blazer might match.

I'm thinking of this dress for the office holiday party and my parents' holiday party, worn with killer heels (possibly red.)  Can you guys give me any style tips to make this more versatile? 

I was thinking of this dress for my and J's holiday party with black tights, long beads, and colorful flats.  I really wish I had brown cowboy boots for this dress, but I don't.  I was also thinking this could work for Thanksgiving.  Thoughts?  I'm more insecure about compiling boho looks than I am about compiling work-appropriate looks.

Guys, I have no excuse for putting these dresses on the shopping list.  I just like them.  They are colorful and pretty and I apparently miss Spring.  I also think they'd make excellent engagement photo or engagement party dresses.  I am absurd, and need to be talked down. 

Thoughts?  Opinions on which four you'd buy?  Opinions on accessories?  Opinions on my (lack of) style?