TBMD

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 - 50% off; similar)
top: J.Crew striped boatneck tee (similar - extra 30% off w/code WEEKEND; similar - 50% off)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
skirt: J.Crew midi skirt in cotton clip-dot (sold here - 30% off w/code WEEKEND)
clutch: Gucci swing leather continental wallet (sold at Gucci / NM; similar - 20% off)
shoes: J.Crew Factory striped espadrille wedges (sold here - 50% off)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code SUMMER50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Abercrombie & Fitch denim (similar - 40% off w/code LONGWKND; similar - 30% off w/code WEEKEND)
top: Ann Taylor lacy sweater shell (similar - extra 40% off; similar)
bracelet: Madewell knot cuff (similar; similar - on sale)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
skirt: J.Crew Collection mixed Italian jacquard faux-wrap (similar - on sale; similar)
bag: J.Crew Downing tote (great dupe; similar; similar - on sale)
nail polish on toes: OPI South Beach Paint My Moji-toes Red (sold here)
shoes: Alexandre Birman Clarita jeweled suede & python flat sandals (sold here - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code SUMMER50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Citrus striped pom-pom scarf (sold here - 30% off; similar - on sale)
dress: Ann Taylor boiled wool pocket dress (similar; similar - extra 40% off)
bracelet: Tory Burch sculpted metal cuff (similar; similar)
clutch: J.Crew Claremont perforated clutch (similar; similar)
nail polish on toes: OPI South Beach Paint My Moji-toes Red (sold here)
shoes: J.Crew jeweled block-heel sandals (sold here - 30% off w/code WEEKEND; similar; similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Gap military (similar; similar - 40% off w/code BRTAKE40)
shirt: J.Crew Factory classic button-down shirt in flannel in buffalo red (similar - on sale; similar - on sale)
top: LOFT fringe festival top (similar - on sale; similar)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam (sold here - $34)
bag: J.Crew Downing tote (great dupe; similar - 33% off; similar - on sale)
shoes: Sperry Top-Sider Bluefish (kids' sold here / women's sold here)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
top: J.Crew striped t-shirt with with pom-poms (sold here - extra 25% off w/code SUMMER)
bracelet: Ann Taylor modern classic skinny bangle (sold here - buy 1 get 1 50% off; similar)
skirt: J.Crew midi skirt in cotton clip-dot (sold here - 25% off w/code SUMMER)
clutch: J.Crew Claremont perforated clutch (similar; similar)
nail polish on toes: OPI South Beach Paint My Moji-toes Red (sold here)
shoes: Alexandre Birman Clarita jeweled suede & python flat sandals (sold here - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Citrus striped pom-pom scarf (sold here; similar - on sale)
blazer: J.Crew Collection Rylan blazer in Italian wool-cotton (similar - 40% off w/code BRTAKE40; similar)
top: Ann Taylor jewel neck long sleeve tee (similar - 40% off; similar - 25% off w/code SUMMER)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam (sold here - $34)
bag: Coach mini Borough bag in retro colorblock (similar; similar - on sale)
shoes: J.Crew Factory striped espadrille wedges (sold here - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
top: J.Crew striped t-shirt with with pom-poms (sold here - extra 25% off w/code SUMMER)
pants: Zara chino trousers (sold here; similar - 25% off w/code SUMMER)
bag: Tory Burch Robinson pebbled square tote (similar)
shoes: Kate Spade Jess pumps (similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 50% off w/code MYSTERY50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: J.Crew Factory fanned jewel necklace (similar - 50% off; similar - 50% off)
blazer: J.Crew double-breasted blazer (sold here; similar - 50% off w/code MYSTERY50)
top: H&M sleeveless ruffle (similar - on sale; similar)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
pants: Zara chino trousers (sold here; similar - 25% off w/code SHOPNOW)
bag: Valentino small glam lock shoulder bag in blush (sold at Net-A-Porter / Farfetch)
shoes: Kate Spade Jess pumps (similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Talbots classic hooded raincoat (similar; similar)
shirt: Banana Republic Dillon-fit vertical stripe shirt (sold here - $39.99; similar - 25% off w/code SHOPNOW)
pants: MICHAEL Michael Kors stretch ankle pants in new navy (sold here; similar)
bag: J.Crew Downing tote (great dupe; similar - 33% off; similar - extra 40% off w/code ENJOY)
shoes: Tory Burch Ludlow driver (similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off w/code HURRY40)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Banana Republic woven chain necklace (similar - on sale)
jacket: Everlane swing trench (sold at Everlane / Spring; similar)
shirt: Banana Republic Dillon-fit vertical stripe shirt (sold here; similar - 25% off w/code EXTRAEXTRA)
watch: The Horse Original watch in rose gold/blush (similar; similar)
pants: Zara chino trousers (sold here; similar)
bag: Nina Ricci small Marche in gris (sold here; rent; similar - 30% off)
shoes: Sole Society Desirae almond toe pump (similar; similar - 50% off)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Burberry Marystow trench coat (similar)
top: Ann Taylor lacy sweater shell (sold here - extra 40% off; similar - extra 40% off)
bracelet: Tory Burch sculpted metal cuff (similar; similar)
pants: Ann Taylor high waist flare trousers (sold here - extra 40% off)
bag: Tory Burch Robinson pebbled square tote (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)
jacket: Talbots classic hooded raincoat (similar; similar)
top: J.Crew striped t-shirt with with pom-poms (may still be in stores)
jeans: LOFT super skinny jeans in deconstructed garden blue (similar - buy 1 get 1 $29.90)
bag: Longchamp large Le Pliage (sold at Bloomingdale's / Nordstrom / NM)
shoes: Sperry Top-Sider Bluefish (kids' sold here / women's sold here)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
blazer: J.Crew Collection Rylan blazer in Italian wool-cotton (similar - extra 50% off; similar)
sweater: Tory Burch Deanna (similar; similar)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
bracelet: Madewell knot cuff (similar; similar - on sale)
jeans: J.Crew Factory Davidson wash skinny jean with 30" inseam (sold here - on sale)
clutch: J.Crew Claremont perforated clutch (similar - on sale; similar)
shoes: Nine West Shindig (similar - 25% off w/code GETSHOPPING; similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Ann Taylor pearlized stone statement necklace (similar - on sale; similar - extra 25% off + free shipping w/code FRIEND)
shirt: Banana Republic Dillon-fit vertical stripe shirt (sold here - 25% off; similar - 25% off w/code GETSHOPPING)
dress: Ann Taylor boiled wool pocket dress (similar; similar - extra 40% off)
bracelet: Tory Burch sculpted metal cuff (similar; similar)
bag: Valentino small glam lock shoulder bag in blush (sold at Net-A-Porter / Farfetch)
shoes: Gap driving moccasins (great dupe; similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Chicwish textured belted trench coat (sold here - on sale; similar; similar)
top: J.Crew striped boatneck tee (similar - extra 25% off w/code GETSHOPPING; similar - 50% off)
watch: The Horse Original watch in rose gold/blush (sold here; similar)
jeans: LOFT super skinny jeans in deconstructed garden blue (similar - buy 1 get 1 $29.90)
bag: Coach mini Borough bag in retro colorblock (similar; similar - on sale)
socks: LOFT elephant and stripe no show sock set (sold here - 40% off)
shoes: Sperry x J.Crew authentic original bow boat shoes (similar)