TBMD

hat: Madewell wool-blend baseball cap (sold at Madewell / Nordstrom - both on sale)
sunglasses: Ann Taylor Lakeside sunglasses (similar - 40% off w/code STEPITUP; similar - 40% off)
coat: J.Crew Majesty peacoat (similar - on sale; similar - on sale)
top: Gap Outlet turtleneck (similar - on sale)
sweater: LOFT cowl sweater tunic (similar - 40% off)
bracelet: David Yurman cable classics bracelet with pearls and diamonds, 5mm - sz S (sold at DY / Saks / Nordstrom)
ring: Etsy milegem morganite ring (sold here)
phone case: Apple smart battery case (sold here)
jeans: LOFT super skinny jeans in deconstructed garden blue (similar; similar; similar)
bag: J.Crew Downing tote (similar; similar)
boots: Stuart Weitzman Lowland over the knee boots in londra - TTS, sz 6 (sold at Nordstrom / Shopbop / Bloomingdale's / Zappos)

hat: Halogen ribbed beanie in grey-combo (sold here - 40% off)
sunglasses: Ann Taylor Lakeside sunglasses (similar; similar - 40% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Levi's cotton twill utility jacket in grey - sz S (sold here; similar - 33% off)
sweater: LOFT cowl sweater tunic (similar; similar - on sale)
bracelet: David Yurman cable classics bracelet with pearls and diamonds, 5mm - sz S (sold at DY / Saks / Nordstrom)
phone case: Apple smart battery case (sold here)
jeans: Caslon stretch skinny jeans in grey adoria wash - sz 25 (sold here - 33% off)
bag: Goyard Artois MM in black/tan (similar)
shoes: Nine West Shindig (similar; similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (similar - 40% off w/code GIVEANDGET; similar - 50% off w/code WRAPITUP)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Cartonnier cropped swing trench via Anthropologie (similar - extra 50% off; similar)
sweater: LOFT cowl sweater tunic (similar; similar)
watch: Olivia Burton midi dial bracelet watch, 30mm in gold - removed 3 links (sold here; similar; similar - 40% off w/code GIVEANDGET)
phone case: Apple smart battery case (sold here)
jeans: Articles of Society Mya skinny jeans in Tahoe (other washes sold here)
bag: Goyard Artois MM in black/tan (similar)
shoes: J.Crew Colette d'orsay pumps in leopard calf hair (similar - 40% off w/code GIVEANDGET; similar)

sunglasses: Ann Taylor Lakeside sunglasses (similar - on sale; similar - 50% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: J.Crew Majesty peacoat (similar - on sale; similar - on sale)
sweater: LOFT cowl sweater tunic (similar; similar)
jeans: LOFT knit denim leggings (similar - on sale; similar - 33% off)
bag: Chanel reissue in 226 (pre-owned; similar)
shoes: Jimmy Choo Romy glittered pumps in tea rose - sz 36 (sold at JC - 30% off / Net-a-Porter - 30% off / Nordstrom; similar)

absolutely love all the details!

sunglasses: Ann Taylor Lakeside sunglasses (similar - $25; similar - 50% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Joules Right as Rain waterproof hooded jacket in antique gold - sz 4 (sold here)
sweater: LOFT cowl sweater tunic (similar; similar)
phone case: Apple smart battery case (sold here)
jeans: Ann Taylor modern all day skinny jeans in stormy mist wash - sz 0 (sold here; similar - 33% off)
bag: Balenciaga city (this season's sold here; similar)
bag strap: J.Crew detachable bag strap in navy ivory (sold here)
shoes: Burberry fringed suede ankle boots (similar - 50% off; similar - 25% off; similar)

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)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: J.Crew Majesty peacoat (similar - on sale; similar - on sale)
sweater: LOFT cowl sweater tunic in forever navy - sz S (this season's sold here - extra 40% off; similar - 50% off)
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)

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

hat: Old Navy sweater-knit pom-pom beanie in black reindeer (similar; similar)
sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: J.Crew Majesty peacoat - sz 00 (this season's sold here - extra 40% off w/code GIFTNOW; similar - 50% off)
sweater: LOFT cowl sweater tunic in forever navy - sz S (sold here - extra 40% off w/code FESTIVE40; similar - 50% off)
jeans: LOFT knit denim leggings (similar - 40% off w/code FESTIVE40; similar)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
shoes: H&M suede ankle boots (similar - 25% off; similar - 33% off)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: H&M (similar - 50% off)
coat: J.Crew Majesty peacoat - sz 00 (this season's sold here - 40% off w/code HOLIDAY)
sweater: LOFT cowl sweater tunic in forever navy - sz S (sold here - 50% off)
phone case: H&M (great dupe; similar - 40% off)
jeans: LOFT knit denim leggings (similar; similar)
bag: Chanel reissue in 226 (pre-owned; similar)
shoes: J.Crew Colette d'orsay pumps in leopard calf hair - TTS, sz 6 (sold here - 40% off w/code HOLIDAY; similar - on sale)

hat: ASOS plain baseball cap (sold here - $7; similar)
sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code PARTY40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: LOFT cowl sweater tunic in forever navy - sz S (sold here - $30)
tee (layered under): J.Crew Factory (similar - 30% off w/code SHOPGIFTS)
phone case: H&M (sold here; similar)
leggings: Zella Live In reversible leggings - sz XS (sold here)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
shoes: Nike Free 5.0 running shoes - sz 6.5 (this season's sold at Nordstrom / Zappos)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code CELEBRATE)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: J.Crew Majesty peacoat - sz 00 (this season's sold here - 40% off w/code HOLIDAY)
sweater: LOFT cowl sweater tunic in forever navy - sz S (sold here - 50% off w/code FRIYAY)
jeans: Articles of Society Mya skinny jeans in Tahoe - sz 25 (sold here)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom / Barney's / Saks)
shoes: Sole Society Desirae almond toe pump (similar; similar - 40% off)