Do you ever have those guilty Saturdays where you drink a whole pot of coffee in the a.m., eat cake at noon, and then settle in front of the tube for a lazy afternoon of hopeless girly flicks? Yep, that’s my Saturday. It is fantastic.

I don’t care who you are; you have to love The Devil Wears Prada. All of that fashion; all of those outfits! It’s just so… delicious. Plus, Anne Hathaway is adorable, and Meryl Streep does a bang-up job playing an Anna Wintour-like fashion icon with an attitude. It is all too reminiscent of my NYC days when I worked the bottom rung as intern in the magazine world, alongside top fashion mags like Vogue and GQ. It was exciting then. But I have to tell you, I am so glad that I chose Portland over Manhattan. I mean, backyard photo shoots with your friends are so much more gratifying than high-stress shoots in the city. Plus, I love my job, and my boss rocks. From what I understand, that’s pretty rare out there in the rat race.

The thing that bothers me most is that fashion is supposed to be fun. We love that our customers send us photos where they are wearing Sock It to Me socks with sneakers and puffers (like Carrie, below). No matter how you choose to wear your socks, it’s all about your individual style.  Whether that’s a cozy, everyday style or a super-chic look with pumps and a mini, it’s all good. Because it’s all you. So thank you, again, for sending us snaps. Keep ’em coming, please!

Look #4: Hurley sweatshirt dress + tights + speckled grey leg warmers + arm warmers + Nebraska vest

I really like the combination of elements here. If you look closely, you can see Carrie’s precious striped flats. They make a good add to a playful outfit like this.  Rocko agrees.

Woot, woot. It’s Friday. Oh my. I am ready for the weekend. Hopefully it’s really long and filled with a good mix of rest and fun and play. That’s all I have to say.

This is one of Carrie’s new fall jackets. I like it because it’s surprisingly versatile for its plaid pattern and is a nice change from the standard solid grey and black jackets we’ve all stashed in our closets over the years. Best of all, it has a super-sized collar that protects the face and neck from the all-too prevalent Oregon rain. Paired with tailored shorts, leggings, socks, and boots, this outfit keeps fashion fresh by showing off some good layered fun… which is my favorite part of fall dressing. Bring on the layers, baby!

Look #3: Plaid jacket + tailored shorts + leggings + Tiny Rose knee-highs + shortie boots

Today is one of those Portland days where the weather wavers between gorgeous and yucky, on and off, all day. It’s annoying. At this point, I’ve learned. But it took me a while. You can pretty much wrap it all up into three rules: One, always carry sunglasses. Two, always bring a raincoat. Three, never expect the weatherman to be right. Once you’ve accepted those key points, you’re set.

Even the fashion-forward know that you simply have to adjust your wardrobe to accommodate our perpetual chance of rain. For instance, suede and satin shoes are most assuredly out. Unless you like playing the roulette wheel of chance, which I don’t recommend.  (“Oh they’ll be fine! I’m sure. I just have to have them.”) Yeah… um, that never works out. Most of us have learned this the hard way. So we started spending our money on rain boots and chic, brimmed caps. You do what you gotta do.

Traditionally, I don’t ever carry an umbrella. I bought this one (below) the day before I moved to Portland, four years ago. Since then, I may have used it once. What can I say? I’m a Portlander now. Umbrellas are out of style. However, it did match my outfit, thus I threw it in for good measure. So there you go. Now I’ve used it twice.

Look #2: Double-breasted wool coat + cap + rubber rain boots + tights + cute socks

Can you tell we had fun shooting these outfits? Oh yes, lots of fun to be had at SITM!

Carrie and I both love fall looks. My favorite part is the boots and socks layered over tights. Carrie’s favorite part: the jackets. Together, I think we make a pretty stylish team. So we decided to rock the photo shoot, round 2. It just so happened that it was a gorgeous fall day. And the leaves had gathered in such a splendid splay of color that our stage seemed straight out of a storybook.

Not unlike our leg warmer photo shoot last June, this “B” rate shoot was nothing short of goofy. After splitting one big Bubba burrito, we raked through her wardrobe, hit the streets, and got to snapping. It was super fun. And slightly dorky. But we’re okay with that.

Look #1: The Bridge & Burn Jacket and Sock It to Me Brown Birds

Keep up with our looks over the next week; we’ll have a new fun look every day!