Here are Gina’s 7 answers to my question, “What items in your closet always make you feel great?”

1. The grey cashmere cardigan from J. Crew that you saw yesterday.  You can find it in great colors for $158 on their site here.  No wonder she was so proud of paying less than $100 a couple of years ago.

2. This shell from Talbot’s that she bought at the beginning of the summer.  We both like the sleeve length (not caps), and it’s made of a light sweater-like fabric.  I think this neckline works because it shows her collarbone.  Just below the collarbone is the highest I like to go.  What about you?

I’m also impressed that the seams in her Madison bra don’t show up more.  This may be the bra that convinces me seams aren’t so bad.

3. This Liberty of London tote that she found in Miami and that always gets compliments.

4. This Land’s End sailor tee that she just bought and has already worn 4 or 5 times.  Several reviewers on the site like its heavy fabric for the cooler weather.  Here’s my question:  Why does this tee look so good on Gina?  It’s a boat neck, for crying out loud!  Last January, I wrote, “My theory is that such a neckline plus horizontal stripes would work together to over-emphasize the bust.”  It looks like my theory was wrong (although I was right when I wrote that such stripes “may even camouflage what’s underneath”).  So here’s my new theory:  Gina makes this look good because she has curves.  Otherwise it would be too boxy.  Another reason might be her 5’8″ height.  I’m kicking myself for not taking a picture of my 5’3″ self in this tee while I was there, just to compare.

Finally, I thought this tee would look great on Gina with some Audrey Hepburn-like tapered pants, but she won’t do it because of her “hourglass calves”.  What??  I have a feeling you’re going to disagree with her when you see her in a dress on Thursday.

See favorites 5, 6 and 7 after the jump.  And see if you notice what one “rule” they each break.

5. Her 5-year-old denim shirt from the Gap. She loves the snaps. I love the darts.  The shirt is too big for her since she lost weight, but that won’t stop her from wearing it.  (I’d like her to order this in a smaller size to see if it would flatter her new size or pull too much at the bust.)

6. This knit navy jacket from Talbot’s (more about the blouse on Thursday).

7. And finally, this J. Crew relaxed boyfriend field jacket.

Have you noticed the rule she’s broken? “No pockets over the chest.”  And in each instance, she gets away with it.  (But let me know if you disagree.)  One reason I think she can do this is that nothing is very fitted.  Except for the Talbot’s shell, everything else is loose.

I’m probably reading way too much into Gina’s favorite choices, but it makes me think of this article by Caroline Weber that Carissa tweeted yesterday.  This quote made me sad:

Over the years I have spent a fortune on sack dresses, unstructured jackets, and oversize cardigans—anything and everything I could find to mask my buxom upper body. A pricey effort, yes, but a successful one, given that every single friend to whom I have mentioned this article has reacted with some version of “No way do you have a big chest!” Prompting me in each case to make the same sheepish confession: “It’s true. I have stealth boobs.”

Caroline Weber’s “stealth boobs” are a mere D cup.