Jennifer Aniston can do no wrong, so when she wears something unconventional, it’s worth paying close attention. Aniston recently stepped out in New York City wearing a dark gray wool Givenchy by Sarah Burton dress paired with golden Christian Louboutin heels and a rich, dark chocolate box bag. It’s an unexpected mix of classic neutrals that somehow elevates the entire look from simply pretty to quite powerful.
While we’d typically pair a primarily gray ensemble with black accessories, Jennifer Aniston is proof that even the oldest outfit recipes don’t have to be followed precisely. When you mix things up, you’ll create something worthy of a stylish double-take. Keep scrolling to shop gray dresses and brown handbags to wear together this autumn and winter.
On Jennifer Aniston: Givenchy dress; Christian Louboutin shoes
Shop Similar Dresses & Purses to Re-create Jennifer Aniston’s Outfit
Look for a dress with asymmetrical neckline or hem — not both.
We love a glimmer of gold hardware on any rich brown bag.
Style this casual dress with your favorite, worn-in brown leather bag.
Imagine this bag in a few years with a perfect patina.
Dark gray also looks great styled with chocolate brown boots and a tan jacket.
Suede adds a interesting textural element to any outfit.
A gray dress always looks great with black accessories, but the outfit is infinitely more interesting when paired with brown.
One word: Espresso.
Try pairing a knit dress with a leather bag for an even more unexpected outfit recipe.
Officially on my wishlist.
This mid-weight knit looks like wool, but is much lighter.
Wear this affordable mini bag with black, gray, or tan.
Whispers of metallic thread make this simple gray dress a great option for holiday party season.
A convertible clutch is a chic option for more formal events.
The subtle plaid pattern is giving major Kate Middleton vibes.
Pair the above dress with a bag from this beloved Edinburgh-based brand.
If your heart is set on wearing wool, Victoria Beckham has you covered.
Go ahead, have fun with it!
