$69, warehouse

A winter statement, suitable for the streets of Manhattan and the slopes of Mammoth!

1. Warehouse sweater,
2. Guerlain mini lipstick set,
3. Shashi beaded bracelet,
4. Rachel Comey crochet bag,
5. Chloe boots,
6. Madewell canvas trousers,

* This bag is on sale at Shopbop, along with just-added winter staples. Shop it !

$245, nordstrom

One way to shake things up a little!

1. Zara dress,
2. Chan Luu earrings,
3. Rodin Lip & Cheek Oil,
4. Frances Valentine fringe bucket bag,
5. Prada buckle strap kitten heels,

$125, farm rio

Sweater weather could use some fun colorful beads, no?

1. Farm Rio beaded sweater,
2. Ganni jacket,
3. Frame jeans,
4. Vasic bucket bag,
5. Anne Sisteron diamond and gold signet ring,
6. Sam Edelman booties,

$168, gap

How I plan to stay chill in the bitter cold. (BTW: the oversized fit is everything!)

1. Isabel Marant sweater,
2. Gap leopard print puffer jacket,
3. Current/Elliot jeans,
4. Gucci velvet bucket bag,
5. Timeless Pearly mismatched earrings,
6. Botkier combat boots,

$59, h&m

Cute now with my still-tan legs and later with tights and boots!

1. H&M leopard print chiffon dress,
2. Oli & Tess earrings,
3. Allison Lou enamel star hoop,
4. Lano Lips Essential Lip Tints,
5. Chanel shearling belt bag,
6. Mansur Gavriel loafers,

$350, shopbop

My fail-proof cold weather strategy in a nutshell.

1. Coach Fair Isle sweater,
2. Chanel Rouge Coco Pink Set,
3. Anne Sisteron gold and pearl hoops,
4. Ulla Johnson pouch,
5. Gianvito Rossi knee-high boots,
6. Petar Petrov leather-timmed skirt,

*I'd use the cute pouch for an evening-out clutch!

While it took my kids a whole week to choose their new backpacks--it is a 180+ school day commitment after all--I decided in about a millisecond that I wanted a big leather clutch. The shape is new and fresh! It's roomy and practical (often sold with a detachable shoulder handle)! And, most importantly, it will do wonders for any outfit. Everyone's going for the Bottega Veneta pouch, above, but here's where I too may need a week to choose: I can't decide between Mansur Gavriel's (way less expensive!) Cloud clutch, Khaite's envelope clutch, or Clare V's woven leather clutch.Thoughts?

$169, mango

Perfect fall dressing in one fell swoop--okay, three: the fringe, the check print, the oversized fit!

1. Joseph cotton jersey t-shirt,
2. Mango fringed blazer,
3. Slverlake jeans,
4. Anne Sisteron freshwater pearl and diamond necklace pendant,
5. Anne Sisteron diamond lock pendant,
6. Mansur Gavriel bag,
7. Steve Madden sandals,

$99, and other stories

Zip up and zen out, all day long.

1. And Other Stories denim jumpsuit,
2. Bauble Bar encrusted star hoops,
3. Kule faux fur tote bag,
4. Maryam Nassir Zadeh wedges,