Yesterday, I visited my favorite second-hand shop, called Second Time Around, where I found the most gorgeous Rebecca Taylor dress in a lovely blue silk. I was bummed to find out that it wasn’t in my size — not even close! With Ms. Taylor on my mind, I began to troll around the web for the dress. While I didn’t find it, I did find some other lovely ones, including this fabulous silk T-shirt dress in a fabric called “sugar.” I love that it’s feminine without being frilly and retro without being a throwback.

As much as I like to be in denial about it, holed up here in my 80-degree apartment, it’s still cold outside. This is both a good and a bad thing — bad because of the obvious, bone chilling truth that winter is actually another three months long; good because that’s another few months of sweater dresses! I want to get cozy in this romantic shift by Rebecca Taylor, which takes the sweater dress to a whole new level with the texture of the slip that peeks out at the hemline.

And for a ladylike dress, I’m picking these very ladylike, chic boots by Etienne Aigner called Davin. Together, this outfit = understated elegance meets a little girly fun.

Back to the chilly, chilly North I go, but I’ve still got warm weather on my mind, which has led me to fall in love with this springtime Rebecca Taylor dress in dusty rose. It gives me (probably false) hope that spring is just around the corner, and I’ll be able to wear light fabrics and breathable shoes again!

And if I can’t, oh well…I’m escaping to warmer climates before all the snow melts anyway. Do you think this dress will hold up nicely in, say, warm Italian summertime air? Speaking of European, how about these cute little flats? They make me think of iced coffee and gondola rides!

The idea of mixing luxurious fabrics like velvet and cashmere makes me feel so cozy and festive and happy that it’s getting cooler out. This season, there’s a ton of lovely velvet out there, done in understated, contemporary cuts. One of my favorites is this short shift from Free People.

Although, I must say that I sort of hate those shoes; it makes the shortness of the dress almost too short. Let’s imagine that she’s wearing these, instead:

As for the combination of luxurious things, I would layer the dress with this gorgeous cashmere faux wrap sweater from Rebecca Taylor. I adore the soft creme color against the almost faded violet of the Free People dress.

The whole outfit is soft, romantic, and exactly right for a perfect fall afternoon walk.

Just when you think it’s fall and you’ve taken out all of your sweaters and gotten excited about being able to wear boots without looking like an idiot, it gets hot again! Well, at least that means that there are still a few more days of wearing sleeveless dresses out to dinner, like Rebecca Taylor’s Chiffon Bib Dress (which is a terrible name for a beautiful frock) on ShopLAStyle.com, a new site that I found thanks the tres fashionable Kathryn!

When it does finally cool down again, though, I’ve found yet another cute sweater dress in Taylor’s Cashmere and Silk Mini Dress.

This cut is really big this season, which rocks for functionality because it keeps your chest and neck covered but not in a librarianesque sort of way. While it’s still above forty degrees outside, I’m all about little flats with tights, like the Belle shoe by Sigerson Morrison on PiperLime. At $260, they’re a little pricier than the equally adorable O-Look flats by Kenneth Cole (on sale for $59).

Now, I never know what to wear with turtlenecks – I don’t really like the way necklaces outside of sweaters look on me, although I think it looks great on other people. Anyway, I’ve found that the best combination is a great pair of earrings and a chunky bracelet. My favorite is the Chunky ID Bracelet paired with the Sunrise Earrings by Vanilla Moon Jewelry designer, and my friend, Cathy Okinaka. Everything she does is hand stamped and absolutely gorgeous.

Okay, so, bottom line is this: while it’s still warm, wear the sleeveless stuff. But don’t despair when it gets chilly, because you can still rock the frock with cashmere, tights, cute shoes, and the perfect jewelry.