TBMD

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 BRSAVE)
top: J.Crew lace panel tank (this season's sold here - 35% off; similar - 40% off)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
skirt: J.Crew daisy lace mini (this season's sold here - on sale; similar - extra 60% off)
bag: J.Crew Downing tote (great dupe; similar - 33% off; similar)
nail polish on toes: OPI South Beach Paint My Moji-toes Red (sold here)
shoes: LOFT Vaughn t-strap sandals (great dupe)

sunglasses: Ann Taylor Metropolis (similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: H&M (similar)
jacket: Chicwish textured belted trench coat (sold here - on sale; similar; similar)
top: Ann Taylor marled short sleeve sweater (similar; similar)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
pants: MICHAEL Michael Kors stretch ankle pants in new navy (sold here - 20% off)
bag: Balenciaga city (this season's sold at NM / Barneys; similar - on sale)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar - on sale)

sunglasses: Ann Taylor Metropolis (similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Ann Taylor estate shimmer (similar - on sale; similar)
sweater: Tory Burch Deanna (similar; similar)
bracelet: Ann Taylor modern classic skinny bangle (sold here - buy 1 get 1 50% off; similar)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
skirt: Ann Taylor floral lace pencil skirt (may still be in stores; similar)
bag: Valentino small glam lock shoulder bag in blush (sold at Net-A-Porter / Farfetch)
shoes: J.Crew Dulci mermaid glitter kitten heels (great dupe; similar)

sunglasses: Ann Taylor Lakeside sunglasses (sold here - 40% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Banana Republic woven chain necklace (similar - on sale)
jacket: UniQUEEN Malang tweed (similar; similar)
top: J.Crew drapey long-sleeve t-shirt (sold here - extra 30% off w/code SCORE)
rings: Ann Taylor pave ring set (sold here - 40% off)
jeans: Express mid rise jean legging in dark 20 (sold here - buy 1 get 1 $29.90)
bag: Balenciaga city (this season's sold at NM / Barneys; similar - on sale)
shoes: Kate Spade Jess pumps (similar)

sunglasses: Ann Taylor Metropolis (similar - 40% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Banana Republic woven chain necklace (similar - on sale)
top: Iris & Ink Thea silk boyfriend shirt (sold here; similar)
rings: Ann Taylor pave ring set (sold here - 40% off)
pants: Zara chino trousers (sold here; similar - 30% off w/code TIMETOSHOP)
bag: Nina Ricci small Marche in gris (sold here; rent; similar - 30% off)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar - on sale)

sunglasses: Ann Taylor Metropolis (similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Ann Taylor pearlized stone statement necklace (similar; similar - on sale)
jacket: Burberry Marystow trench coat (similar)
dress: Ann Taylor boiled wool pocket dress (similar - extra 50% off; similar - extra 60% off)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
clutch: Tory Burch Kerrington carryall (similar)
shoes: Valentino Rockstud leather cage flats in watercolor (other colors sold here, here; similar - 20% off)

sunglasses: Ann Taylor Metropolis (similar - 50% off + free shipping w/code CYBER50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Banana Republic woven chain necklace (similar - on sale)
jacket: Chicwish textured belted trench coat (sold here - on sale; similar; similar)
top: J.Crew drapey long-sleeve t-shirt (sold here - on sale)
rings: Ann Taylor pave ring set (sold here - 50% off + free shipping w/code CYBER50)
skirt: Ann Taylor floral lace pencil skirt (may still be in stores; 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 - on sale)

hat: MLB Washington Nationals cap (this season's sold here)
sunglasses: Ann Taylor Metropolis (similar - 50% off + free shipping w/code CYBER50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Everlane swing trench (sold here; similar - on sale; similar)
shirt: J.Crew Factory classic button-down shirt in flannel in buffalo red (similar - on sale; similar - on sale)
top: Everlane the women's V tee (sold here; similar - on sale)
jeans: LOFT knit denim leggings (similar - extra 30% off w/code WOOF)
bag: Longchamp large Le Pliage (sold at Bloomingdale's / Nordstrom / NM)
shoes: Nike Free 5.0 running shoes (sold at Finish Line - 20% off / Zappos / Net-A-Porter)

sunglasses: Ann Taylor Metropolis (similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Ann Taylor faux fur scarf (similar; similar)
jacket: Cartonnier cropped swing trench (similar - extra 40% off; similar)
sweater: LOFT relaxed turtleneck tunic (similar - extra 30% off w/code WOOF; similar)
tee (layered under): Ann Taylor jewel neck long sleeve tee (similar)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
jeans: LOFT knit denim leggings (similar - extra 30% off w/code WOOF)
bag: Longchamp large Le Pliage (sold at Bloomingdale's / Nordstrom / NM)
shoes: H&M suede ankle boots (similar; similar)

sunglasses: Ann Taylor Metropolis (similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: Ann Taylor striped mock neck (similar - extra 40% off w/code 24HOURS)
tee (layered under): J.Crew Factory (this season's sold here - extra 40% off w/code 24HOURS)
bracelet: Madewell knot cuff (similar; similar - on sale)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
pants: Zara chino trousers (sold here; similar)
bag: Coach mini Borough bag in retro colorblock (similar; similar - on sale)
keychain (on bag): Shinhwa faux fur pom keychain (sold here)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's / BG / NM; similar)

sunglasses: Ann Taylor Metropolis (similar - 50% off w/code SPRING50)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here - 10% off w/code BINOTE)
jacket: Burberry Marystow trench coat (similar)
top: Ann Taylor lacy sweater shell (sold here - extra 50% off w/code SPRING50; similar - extra 50% off w/code SPRING50)
ring: Elizabeth and James Windrose (sold at Bloomingdale's / Shopbop; similar)
bracelet: Madewell knot cuff (similar; similar - on sale)
pants: Chelsea28 pleated wide leg pants (similar; similar)
bag: Valentino small glam lock shoulder bag in blush (sold at Net-A-Porter / Farfetch)
shoes: Zara mid-heel patent court pumps (similar - on sale; similar)

sunglasses: Ann Taylor Metropolis (similar - 40% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Ann Taylor faux fur scarf (similar; similar)
jacket: Zara short quilted jacket (similar - on sale; similar - on sale)
sweater: Tory Burch Deanna (similar; similar)
jeans: LOFT knit denim leggings (similar - extra 50% off)
bag: J.Crew Downing tote (great dupe; similar)
shoes: H&M suede ankle boots (similar; similar)

sunglasses: Ann Taylor Metropolis (similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Forever 21 chain (similar; similar)
blazer: J.Crew Collection Rylan blazer in Italian wool-cotton (similar - extra 40% off; similar)
top: Ann Taylor lacy sweater shell (sold here - extra 40% off; similar - extra 40% off)
pants: Zara chino trousers (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 - 25% off w/code FRIENDS)

sunglasses: Ann Taylor Metropolis (similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
scarf: Ann Taylor faux fur scarf (similar; similar)
sweater: LOFT relaxed turtleneck tunic (similar - extra 40% off; similar)
top (layered under): Ann Taylor jewel neck long sleeve tee (similar - extra 25% off w/code SHOPSALE)
ring: Elizabeth and James Windrose (sold at Bloomingdale's - 25% off w/code FRIENDS / Shopbop - 25% off w/code INTHEFAM; similar)
pants: MICHAEL Michael Kors stretch ankle pants in new navy (sold at Nordstrom / Bloomingale's - 25% off w/code FRIENDS)
keychain (on bag): Shinhwa faux fur pom keychain (sold here)
bag: Tory Burch Robinson pebbled square tote (small size sold here; similar)
shoes: Kate Spade Jess pumps (similar)

hat: MLB Washington Nationals cap (this season's sold here)
sunglasses: Ann Taylor Metropolis (similar - 40% off)
sweater: H&M pile-lined cardigan (similar - 33% off)
top: J.Crew drapey long-sleeve t-shirt (sold here - extra 30% off w/code SPRINGSTYLE)
pants: Blank NYC faux leather skinny (sold here)
bag: Longchamp large Le Pliage (sold at Bloomingdale's / Nordstrom / NM)
shoes: Nike Free 5.0 running shoes (sold at Finish Line - 20% off / Zappos / Net-A-Porter)

sunglasses: Ann Taylor Metropolis (similar - 40% off)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
coat: Burberry Brit Daylesmoore (sold at Nordstrom / Saks / NM)
turtleneck: J.Crew oversize stripe turtleneck (similar - extra 30% off w/code SHOPNOW; similar - on sale)
vest: Express sleeveless one-button jacket (similar; similar)
pants: Zara chino trousers (sold here; similar)
keychain (on bag): Shinhwa faux fur pom keychain (sold here)
bag: Nina Ricci small Marche in gris (sold here; rent; similar)
shoes: Sole Society Desirae almond toe pump (similar; similar - extra 20% off w/code SHOPNOW; similar - on sale)