TBMD

sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores; similar - $15)
scarf: BP. check woven square scarf (similar - 50% off; similar)
jacket: Zara short quilted jacket (this season's sold here; similar - on sale)
top: Ann Taylor ponte side tie top - sz XS (sold here - extra 50% off; similar)
jeans: LOFT knit denim leggings (similar - extra 40% off; similar)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
socks: LOFT (similar)
boots: Burberry exploded check rainboots (similar - on sale; similar - 20% off)

sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Massimo Dutti nappa biker jacket (similar - 35% off; similar)
sweater: H&M pile-lined cardigan
top: Madewell whisper cotton turtleneck in wellton stripe - sz XS (sold here - $24.99)
jeans: Articles of Society Mya skinny jeans in Tahoe (other washes sold here)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
shoes: J.Crew Colette d'orsay pumps in leopard calf hair - TTS, sz 6 (sold here - on sale; similar - 50% off; similar)

sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: Polo Ralph Lauren cable wool cashmere poncho - sz XS (sold here - $64.99)
top: Gap Factory long-sleeve turtleneck - sz S (sold here - $11.97; similar - extra 50% off w/code SALEFUN)
jeans: LOFT super skinny jeans in deconstructed garden blue (similar; similar)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
boots: Stuart Weitzman Lowland over the knee boots in londra - TTS, sz 6 (sold at Nordstrom / Revolve Clothing / Bloomingdale's / Zappos)

sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: Abercrombie & Fitch mixed rib coatigan - sz S (sold here - 40% off)
top: Zara peplum poplin top (similar - 60% off; similar - on sale)
watch: The Horse Original watch in rose gold/blush (sold here; similar - on sale; similar)
phone case: H&M (great dupe; similar)
jeans: LOFT knit denim leggings (similar - extra 40% off w/code NEWNOW; similar)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom / Barney's / Saks)
shoes: J.Crew Colette d'orsay pumps in leopard calf hair - TTS, sz 6 (sold here - extra 30% off w/code ADDTOBAG; similar - 50% off)

[left]: outfit details   /   [right]: outfit details below

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Levi's cotton twill utility jacket - sz S (sold here - 45% off; similar - 33% off)
shirt: J.Crew Factory classic button-down shirt in flannel in buffalo red (similar - on sale)
dress: Gap double-layer linen-cotton dress - sz XS (this season's sold here - extra 40% off w/code HAPPY)
bag: J.Crew Downing tote (great dupe; similar; similar - on sale)
shoes: H&M suede ankle boots (similar - 40% off; similar - 60% off)