TBMD

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Ann Taylor faux fur scarf (similar - on sale; similar - on sale)
jacket: Zara short quilted jacket (this season's sold here; similar - on sale)
sweater: LOFT shawl open cardigan (current version sold here; similar - extra 40% off)
top: Gap winter graphic long sleeve tee - sz S (sold here - extra 25% off w/code MORE)
jeans: LOFT knit denim leggings (similar - extra 40% off; similar)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
shoes: Burberry fringed suede ankle boots (similar; similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: Polo Ralph Lauren cable wool cashmere poncho - sz XS (sold at RL - $59.99 w/code EXTRA40 / Lord & Taylor - extra 20% off w/code FINAL)
turtleneck: Madewell whisper cotton turtleneck in wellton stripe - sz XS (sold here - on sale)
jeans: Articles of Society Mya skinny jeans in Tahoe - sz 25 (other washes sold here)
keychain (on bag): Shinhwa faux fur pom keychain (similar)
bag: Tory Burch Robinson pebbled square tote (similar; similar)
shoes: J.Crew Colette d'orsay pumps in leopard calf hair - TTS, sz 6 (sold here - extra 40% off w/code GETSHOPPING; similar - 35% off)

hat: ASOS plain baseball cap (sold here - $5.50; similar)
sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Abercrombie & Fitch woven scarf (sold here - on sale)
jacket: Massimo Dutti nappa biker jacket (similar - 35% off; similar)
top: Vince jersey slub tee (similar - 55% off; similar - extra 40% off w/code GOGO)
phone case: H&M (great dupe; similar)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam - sz 25 (sold here - extra 35% off + free shipping w/code THECOOLEST)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom / Barney's / Saks)
shoes: Sperry Seacoast canvas sneakers - sz 6.5 (sold at Lord & Taylor - 15% off w/code FINAL / Macy's)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code SHOP40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: J.Crew classic duffle coat (similar - on sale; similar - on sale)
turtleneck: J.Crew oversize stripe turtleneck (similar - on sale; similar)
phone case: H&M (great dupe; similar)
skirt: J.Crew Factory double serge mini (this season's sold here - extra 40% off w/code SHOPSALE)
tights: Forever 21 plain knit tights in grey (similar - 50% off w/code NOEXCUSES; similar)
bag: Coach mini Borough bag in retro colorblock (similar; similar - on sale)
shoes: Talbots Georgina flats with embroidered scotty dog - runs narrow, sz 6.5 (sold here - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code SHOP40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: H&M (similar - 50% off)
blazer: J.Crew Collection Rylan blazer in Italian wool-cotton (similar)
sweater: Tory Burch Deanna (similar - 30% off; similar)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam - sz 25 (sold here - on sale)
bag: Valentino small glam lock shoulder bag in blush (sold here)
shoes: J.Crew Colette d'orsay pumps in leopard calf hair - TTS, sz 6 (sold here - extra 40% off w/code SHOPSALE; similar - 50% off)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: Polo Ralph Lauren cable wool cashmere poncho - sz XS (sold at RL - $59.99 w/code SNOW / Lord & Taylor - extra 20% off w/code FINAL)
top: Gap Factory long-sleeve turtleneck - sz S (sold here - up to 52% off; similar - on sale)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
clutch: Gucci swing leather continental wallet (sold here; similar)
pants: Blank NYC faux leather skinny pants - sz 26 (sold at Lord & Taylor - 15% off w/code FINAL / Shopbop)
shoes: YSL Charlotte pumps in Millennium print (great dupe sold here - 40% off, here)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code WOW40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Massimo Dutti nappa biker jacket (similar - 35% off; similar)
sweatshirt: Abercrombie & Fitch sherpa-lined full-zip hoodie in navy - sz M (similar - extra 40% off w/code GREAT; similar - extra 40% off w/code 15913)
top: J.Crew drapey long-sleeve t-shirt (similar - on sale; similar - 40% off)
phone case: H&M (great dupe; similar)
jeans: Articles of Society Mya skinny jeans in Tahoe - sz 25 (other washes sold here)
bag: Balenciaga city (this season's sold here; similar)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar - 10% off)

hat: Old Navy sweater-knit pom-pom beanie in black reindeer (similar - on sale)
sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code WOW40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: LOFT herringbone plaid infinity scarf (this season's sold here - $14)
jacket: Abercrombie & Fitch hard shell performance jacket - sz M (sold here - extra 40% off w/code 19153; similar - extra 40% off w/code WINTER)
top: Ann Taylor ponte side tie top - sz XS (sold here - extra 60% off; similar - 40% off)
jeans: LOFT knit denim leggings (similar - extra 60% off; similar)
bag: Coach mini Borough bag in retro colorblock (similar)
shoes: Nike Free 5.0 running shoes - sz 6.5 (this season's sold at Nordstrom / Zappos)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: H&M (this season's sold here; similar - 60% off)
coat: Burberry Brit Daylesmoore - sz 2 (sold here - 30% off; similar; similar - on sale)
top: Ann Taylor striped ruffle neck blouse (similar - 32% off)
jeans: LOFT knit denim leggings (similar - extra 60% off; similar)
bag: Coach mini Borough bag in retro colorblock (similar)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar - 10% off)

hat: Old Navy sweater-knit pom-pom beanie in black reindeer (similar - on sale; similar - on sale)
sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code WINTER40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: J.Crew classic duffle coat (similar - on sale; similar - on sale)
sweatshirt: Abercrombie & Fitch sherpa-lined full-zip hoodie in navy - sz M (similar - extra 40% off w/code GOODSTART; similar - 30% off)
top: Gap Factory long-sleeve turtleneck - sz S (sold here - up to 52% off; similar - extra 40% off w/code MUSTSHOP)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam - sz 25 (sold here - extra 40% off w/code THISISBIG)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
shoes: Talbots Georgina flats with embroidered scotty dog - runs narrow, sz 6.5 (sold here - $49.99)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code WINTER40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: Canada Goose Victoria parka - sz XS (sold at Nordstrom / Bloomingdale's / Shopbop / Revolve Clothing / NM)
sweater: LOFT shawl open cardigan (similar; similar - extra 60% off)
top: Gap winter graphic long sleeve tee - sz S (sold here - 40% off w/code WINTER)
phone case: H&M (great dupe; similar)
jeans: LOFT knit denim leggings (similar; similar)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
boots: Miu Miu suede pointed toe over the knee (similar; similar - 60% off)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code WINTER40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Zara two-tone checked scarf (similar)
jacket: Massimo Dutti nappa biker jacket (similar; similar)
top: Ann Taylor striped ruffle neck blouse (similar - 32% off)
jeans: LOFT knit denim leggings (similar; similar)
bag: Chanel reissue in 226 (pre-owned; similar; similar)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar)

hat: Old Navy sweater-knit pom-pom beanie in black reindeer (similar - on sale; similar - on sale)
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)
sweatshirt: Abercrombie & Fitch sherpa-lined full-zip hoodie in navy - sz M (similar - 40% off w/code YAY; similar - 30% off)
top: J.Crew striped t-shirt with with pom-poms (this season's sold here)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam - sz 25 (sold here - $17.99 w/code SHOPCREW)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
shoes: Talbots Georgina flats with embroidered scotty dog - runs narrow, sz 6.5 (sold here - $59.99)