TBMD

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 20%+ off w/code TREAT)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Banana Republic woven chain necklace (similar - 15% off w/code OCTOBER)
jacket: Chicwish textured belted trench coat - sz S (sold here - on sale; similar)
top: Ann Taylor striped ruffle neck blouse - sz XS (sold here - 20%+ off w/code TREAT)
rings: Ann Taylor pave ring set (similar - 20%+ off w/code TREAT)
phone case: H&M (sold here; similar)
skirt: LOFT floral lace pencil skirt (similar - extra 30% off w/code SALETREAT; similar - 40% off)
bag: Nina Ricci small Marche in gris (sold here; rent; similar)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar)

hat: ASOS plain baseball cap (sold here - $7)
sunglasses: Ann Taylor Lakeside sunglasses (sold here)
jacket: Abercrombie & Fitch hard shell performance jacket - sz M (sold here)
top: Old Navy relaxed boat-neck tee (similar; similar - on sale)
jeans: Articles of Society Mya skinny jeans in Tahoe (sold here)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom)
shoes: Sperry Top-Sider Angelfish boat shoes in linen/oat (sold at Lord & Taylor - extra 15% off w/code OCTOBER / Zappos / Macy's / shoebuy)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: LOFT button back sweater (sold here - extra 50% off)
bracelet: Banana Republic wildflower cuff (similar - on sale; similar)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
phone case: H&M (sold here; similar)
skirt: J.Crew midi skirt in cotton clip-dot (may still be in stores; similar - extra 15% off w/code OCTOBER)
bag: Coach mini Borough bag in retro colorblock (similar - on sale)
shoes: J.Crew Factory striped espadrille wedges (similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Cartonnier cropped swing trench (this season's sold here - free shipping; similar - 40% off)
dress: Ann Taylor boiled wool pocket dress (similar; similar)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
bracelet: Banana Republic wildflower cuff (similar - on sale; similar)
phone case: H&M (sold here; similar)
bag: Chanel reissue in 226 (pre-owned; similar)
shoes: Nine West Shindig (similar; similar)

hat: ASOS plain baseball cap (sold here - $7.50)
sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/OCTOBER50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweatshirt: Abercrombie & Fitch sherpa-lined full-zip hoodie in navy - sz M (similar - 40% off w/code ALLIN; similar)
top: Banana Republic roll-sleeve crew tee in white (similar - extra 40% off w/code ALLIN)
phone case: H&M (sold here; similar)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam (sold here - $29.99)
bag: J.Crew Factory canvas tote bag (similar; similar - 40% off w/code ALLIN)
shoes: J.Crew Factory striped espadrille wedges (similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code OCTOBER50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: BP. check woven square scarf (sold here)
top: Ann Taylor faux leather yoke top (similar - 50% off w/code OCTOBER50; similar - 40% off w/code GAMEON)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
jeans: Articles of Society Mya skinny jeans in Tahoe (sold here)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom)
shoes: YSL Charlotte pumps in Millennium print (pre-owned sold here; great dupe sold here, here)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code OCTOBER50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Cartonnier cropped swing trench (this season's sold here; similar - 40% off)
top: J.Crew Factory oversized turtleneck in stripe (similar; similar - 40% off)
jeans: Articles of Society Mya skinny jeans in Tahoe (sold here)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom)
shoes: Sperry Top-Sider Angelfish boat shoes in linen/oat - sz 6 (sold at Lord & Taylor - extra 25% off w/code FRIENDS / Zappos / Macy's / shoebuy)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Simply Vera Vera Wang silver-tone cluster (similar - 40% off w/code FALL; similar; similar)
sweater: LOFT button back sweater - sz XS (sold here - extra 40% off)
rings: Ann Taylor pave ring set (similar)
skirt: LOFT floral lace pencil skirt (similar - extra 30% off w/code STARTSHOPPING; similar - 40% off)
scarf: Ann Taylor faux fur scarf (this season's sold here; similar)
bag: Nina Ricci small Marche in gris (sold here; rent; similar)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar)

hat: ASOS plain baseball cap (sold here - $7.50)
sunglasses: Ann Taylor Lakeside sunglasses (sold here)
jacket: Burberry lightweight belted parka (similar; similar)
top: J.Crew striped boatneck tee (similar - 30% off w/code GETSHOPPING; similar - on sale)
watch: The Horse Original watch in rose gold/blush (sold here; similar)
shorts: Express 2 1/2 inch low rise destroyed cuffed denim (similar - on sale)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
socks: LOFT charm knee high socks (similar - BOGO 50% off)
boots: Hunter original Tour packable rain boots (sold at Nordstrom / Zappos / Bloomingdale's / NM / Saks)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Abercrombie & Fitch denim (similar - 40% off w/code YAY; similar)
top: Ann Taylor lacy sweater shell (similar - 40% off w/code TOPS40; similar - extra 40% off)
belt: J.Crew Factory (similar - 40% off; similar - extra 40% off w/code YAY)
bracelet: Banana Republic wildflower cuff (similar - on sale; similar)
phone case: H&M (sold here; similar)
pants: MICHAEL Michael Kors stretch ankle pants in new navy (sold here; similar)
bag: Tory Burch Robinson pebbled square tote (similar; similar)
shoes: Kate Spade Jess pumps (similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: H&M (similar; similar)
blazer: Topshop Emery Tonic boyfriend blazer - sz US 4 (sold here; similar)
top: Zara peplum poplin top (may still be in stores; similar; similar - extra 40% off)
watch: The Horse Original watch in rose gold/blush (sold here; similar)
jeans: Articles of Society Mya skinny jeans in Tahoe (sold here)
bag: Saint Laurent medium Universite bag (sold at Saint Laurent / Nordstrom)
shoes: Sole Society Desirae almond toe pump (similar; similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code FALL50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Abercrombie & Fitch denim (similar - 40% off w/code CRISP; similar - extra 30% off w/code YESPLEASE)
top: J.Crew Factory striped knit top (sold here - on sale; similar - extra 30% off w/code YESPLEASE)
clutch: Gucci swing leather continental wallet (sold at Gucci / NM; similar)
skirt: J.Crew midi skirt in cotton clip-dot (may still be in stores; similar - extra 20% off w/code COLUMBUS)
nail polish on toes: OPI South Beach Paint My Moji-toes Red (sold here)
shoes: J.Crew mixed gingham sandals with ankle wrap - sz 6.5 (sold at J.Crew / Net-a-Porter)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code FALL50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Cartonnier cropped swing trench (this season's sold here)
top: Ann Taylor striped ruffle neck blouse - sz XS (sold here - 50% off w/code FALL50)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
phone case: H&M (sold here; similar)
jeans: Articles of Society Mya skinny jeans in Tahoe (sold here)
bag: Chanel reissue in 226 (pre-owned; similar - 30% off)
shoes: Sole Society Desirae almond toe pump (similar; similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Ann Taylor pearlized stone statement necklace (this season's sold here - 40% off)
scarf: Ann Taylor faux fur scarf (similar)
top: Banana Republic long-sleeve cozy top - sz XS (sold here - 40% off)
rings: Ann Taylor pave ring set (similar - 40% off)
phone case: H&M (sold here; similar)
skirt: LOFT floral lace pencil skirt (similar - extra 40% off w/code YESPLEASE; similar - 50% off)
bag: Chanel camellia WOC (sold here; similar)
shoes: Valentino bow ballerina flats (similar - 40% off; similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: J.Crew Factory tassel scarf (similar)
top: LOFT flecked two-in-one sweater (similar - 25% off w/code WEARNOW)
phone case: H&M (sold here; similar)
shorts: Express 2 1/2 inch low rise destroyed cuffed denim (similar - on sale)
bag: Balenciaga city (this season's sold at NM / Barneys; similar)
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)
top: J.Crew striped boatneck tee (similar; similar - on sale)
bracelet: J.Crew Factory gold and crystal link bracelet (sold here - on sale; similar)
skirt: J.Crew midi skirt in cotton clip-dot (sold here - extra 30% off w/code WEARNOW)
bag: Valentino small glam lock shoulder bag in blush (sold here; similar)
shoes: Loeffler Randall Rae in rose gold (similar - on sale; similar)