TBMD

sunglasses: Ann Taylor Lakeside sunglasses (similar - on sale; similar - 30% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Banana Republic camo sheer rectangular scarf (check for re-stock; similar)
jacket: Levi's cotton twill utility jacket in grey - sz S (sold here; similar - 33% off)
top: Gibson twist front cozy fleece pullover in black - sz XS (sold here; similar)
jeans: Caslon stretch skinny jeans in grey adoria wash - sz 25 (sold here - 33% off)
bag: Saint Laurent medium Universite bag (sold here; similar)
shoes: Manolo Blahnik gray suede BB pumps in 70mm - sz 36.5 (sold at Nordstrom / NM / Barney's; similar)

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 - $25; similar - 50% off + free shipping w/code GIFTAWAY)
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 - on sale)
sweater: Abercrombie & Fitch mixed rib coatigan (similar - 40% off; similar)
top: J.Crew embroidered floral top - runs big, sz XXS (sold here - on sale)
phone case: Apple smart battery case (sold here)
jeans: Articles of Society Mya skinny jeans in Tahoe (other washes sold here)
bag: J.Crew Signet bag in Italian leather in sun (this season's sold here)
shoes: Sole Society Desirae almond toe pump (similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (similar - 50% off w/code GOPINK; similar - 50% off w/code FRIYAY)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Levi's cotton twill utility jacket - sz S (sold here; similar - on sale)
sweater: Massimo Dutti knit sweater with lace detail (similar - 30% off; similar)
phone case: Apple smart battery case (sold here)
jeans: LOFT super skinny jeans in deconstructed garden blue (similar - 40% off; similar - 30% off)
bag: Balenciaga city (this season's sold here; similar)
bag strap: J.Crew detachable bag strap in navy ivory (sold here - 40% off w/code THANKU)
boots: Stuart Weitzman Lowland over the knee boots in londra - TTS, sz 6 (sold at Nordstrom / Shopbop - 25% off w/code MORE17 / Bloomingdale's / Zappos - 30% off)

sunglasses: Ann Taylor Lakeside sunglasses (similar - $25; similar - $12)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: LOFT herringbone plaid infinity scarf (similar - 40% off; similar - 40% off)
jacket: Levi's cotton twill utility jacket - sz S (sold here; similar - 33% off)
shirt: Old Navy classic plaid flannel shirt in black watch (this season's sold here; 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)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Net-a-Porter; similar)
shoes: Sole Society Desirae almond toe pump (similar - on sale)

hat: ASOS plain baseball cap (similar)
sunglasses: Ann Taylor Lakeside sunglasses (similar - 50% off w/code SPRING50; similar - 50% off + free shipping w/code CYBER)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Levi's cotton twill utility jacket (similar - 33% off; similar - 33% off)
sweater: LOFT shawl open cardigan (similar - extra 50% off w/code CYBER; similar - on sale)
top: Gap geo lace three-quarter top (similar - extra 40% off w/code GOODEGG)
leggings: Zella Live In reversible leggings - sz XS (sold here)
bag: Madewell canvas transport tote (sold at Madewell / Nordstrom / Shopbop - 20% off w/code EVENT17)
shoes: New Balance for J.Crew 711 mesh sneakers in confetti - sz 6.5 (sold here)

[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)

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)

hat: ASOS plain baseball cap (sold here - $5.50; similar)
sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code HOLIDAY50)
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)
sweater: LOFT shawl open cardigan (similar - 50% off; similar - 50% off w/code HOLIDAY50)
top: Gap winter graphic long sleeve tee - sz S (sold here - 40% off w/code WINTER)
jeans: LOFT knit denim leggings (similar - 40% off w/code FESTIVE40; similar)
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 (may still be in stores)
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)
shirt: J.Crew Factory classic button-down shirt in flannel in buffalo red (this season's sold here - on sale; similar - 40% off w/code BRHOLIDAY)
top: Vince Little Boy tee (similar; similar - 51% off w/code HAPPY)
jeans: LOFT knit denim leggings (similar - 40% off w/code FESTIVE40; similar)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom / Barney's / Saks)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Ann Taylor blanket stripe scarf (this season's sold here; similar)
jacket: Levi's cotton twill utility jacket - sz S (sold here - 33% off)
top: Banana Republic long-sleeve cozy top - sz XS (sold here - on sale)
phone case: H&M (sold here; similar)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam - sz 25 (sold here - extra 35% off w/code THISISFUN)
bag: Balenciaga city (this season's sold at NM / Barneys; similar)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar)