TBMD

sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: Abercrombie & Fitch mixed rib coatigan - sz S (sold here - 40% off)
dress: theory Betty dress in sevona fabric - sz 2 (sold here; similar - 40% off)
phone case: H&M (great dupe; similar)
bag: Nina Ricci small Marche in gris (sold here - 40% off; rent; similar; similar)
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; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Abercrombie & Fitch woven scarf (sold here - $11.40)
blazer: J.Crew Collection Rylan blazer in Italian wool-cotton (similar - on sale)
top: Banana Republic long-sleeve cozy top (similar - extra 40% off w/code FFSALE)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam (similar)
luggage tag (on bag): J.Crew anchor embossed bag tag (similar - on sale)
bag: Tory Burch Robinson pebbled square tote (similar; similar)
shoes: Kate Spade Jess pumps (similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores; similar - 30% off w/code SPRING17)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: J.Crew classic duffle coat (similar - on sale)
sweater: Abercrombie & Fitch mixed rib coatigan - sz S (sold here - 60% off)
top: Gap geo lace three-quarter top (similar - extra 40% off w/code FFSALE)
jeans: LOFT super skinny jeans in deconstructed garden blue (similar; similar)
bag: J.Crew Downing tote (great dupe; similar; similar - on sale)
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; similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: Burberry Brit Daylesmoore (this season's sold here; similar - on sale)
top: J.Crew Factory oversized turtleneck in stripe (similar - 30% off)
jeans: LOFT super skinny jeans in deconstructed garden blue (similar; similar)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom / Barney's / Saks)
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 (sold here; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Abercrombie & Fitch hard shell performance jacket (similar - extra 40% off w/code TUESDAY; similar - extra 40% off)
sweater: LOFT cowl sweater tunic in forever navy - sz S (sold here - extra 40% off)
phone case: H&M (great dupe; similar)
jeans: LOFT knit denim leggings (similar - extra 40% off; similar)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
boots: Hunter original Tour packable rain boots - TTS, sz 6 (sold at Nordstrom / Zappos / Bloomingdale's / Saks)

sunglasses: Ann Taylor Lakeside sunglasses (sold here; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: BP. check woven square scarf (similar; similar)
coat: Burberry Brit Daylesmoore (this season's sold here; similar - on sale)
jeans: LOFT knit denim leggings (similar - extra 40% off; 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; similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Ann Taylor blanket stripe scarf (similar - on sale)
jacket: UniQUEEN Malang tweed (similar - on sale)
top: Iris & Ink Thea silk boyfriend shirt (similar; similar)
phone case: H&M (great dupe; similar)
jeans: LOFT super skinny jeans in deconstructed garden blue (similar; similar)
bag: Nina Ricci small Marche in gris (sold here; rent; similar)
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; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Balenciaga original moto leather jacket in parme (similar - 25% off; similar)
top: Madewell whisper cotton turtleneck in wellton stripe - sz XS (sold here - $14.99)
dress: Ann Taylor boiled wool pocket dress (similar - on sale)
bag: Nina Ricci small Marche in gris (sold here; rent; similar)
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; 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)