Full disclosure: one of my favorite romantic comedies in recent years is The Proposal. The movie came out in June 2009, and stars the Sexiest Man Alive Ryan Reynolds alongside America’s sweetheart, Sandra Bullock. She plays Margaret Tate, a tough-as-nails book editor who convinces her assistant Andrew Paxton (played by Reynolds) to marry her so she can avoid deportation (to Canada) and he can keep his job. Since an immigration officer is suspicious the pair are committing fraud, they travel to Andrew’s Alaskan hometown in an attempt to prove they’re the real deal.

I love that the movie is heavy on the physical comedy and light on the “romance” part, like old-school romantic comedies (think Bringing Up Baby). And who can forget this hysterical scene?  It wasn’t until I re-watched the movie last weekend with my friends Alyssa, Nancy, Katie, Juliane, Bobby, and Vince though that I realized how stylish Sandra Bullock’s wardrobe is! It’s simple but sophisticated, and appropriate and comfortable enough to wear during winter break catching up with family and friends. Okay, you might have to throw on a coat, but you get the idea.

Look 1: Surprise Engagement

When Margaret and Andrew first arrive, his family throws him a surprise welcome home party. The real surprise though is when Margaret and Andrew announce their engagement. A similar outfit is a great look for almost any holiday party!

Party Dress- Dorothy Perkins; Pumps- Payless; Nail polish- Essie, Earrings- Kate Spade (Nordstrom); Clutch- Forever 21.

At the party, Margaret wears this fabulous form-fitting gray dress: sexy and sophisticated. It was hard to find a similar dress, but this one-shoulder dress is perfect for a younger crowd. It’s still comes in that shiny pewter color and I love the slightly structured silhouette. Like the original dress, it’s eye-catching and classy. I read that the movie’s costume designer was inspired by 1940s fashions, so I used that as a jumping board to pick out the accessories. A faux snakeskin clutch with simple hardware adds a retro vibe, as do the the red jewel earrings. Paint your nails in a matching red (not too deep, not too bright) for another pop of color. The pumps may not be Louboutin, but they have the right amount of height and the fun rosette detail to keep things youthful. Finish off with a high and sleek straight ponytail, just like Sandra.

Look 2: Cozy Comfort

Margaret wears this comfortable and chic outfit when she goes into town with Andrew, and of course, in that epic chant scene with Betty White. Black and yellow can go badly together, but this is how to do it right. This outfit is perfect for lounging around with friends or a coffee date.

Long-sleeved tee- Topshop; V-neck sweater- Uniqlo; Jeggings- John Lewis; Sunglasses- ASOS; Striped scarf- Debenhams; Flats- Payless.

Start with a basic long-sleeved white shirt and slim black jeggings. Add a warm and soft sweater in a mustard yellow, one of the fall’s most popular colors. The striped black and white scarf adds interest. Black ballet flats keep the look polished an put together. I added the sunglasses because Margaret wears similar shades when she first comes to Alaska.

Bonus Look: Grace Paxton

Margaret isn’t the only fashionable woman in the movie. Andrew’s mom Grace (played by Mary Steenburgen) also has a comfortably chic fashion taste. I tried to put together a look perfect for a day with friends or maybe out shopping.