TBMD

sunglasses: Ann Taylor Lakeside sunglasses (similar - 50% off w/code SPRING50; similar - 40% off w/code FRIEND)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: LOFT fringe tweed jacket (similar - extra 40% off w/code FRIEND; similar - on sale)
dress: Ann Taylor boiled wool pocket dress (similar - 50% off)
bracelet: Tory Burch sculpted metal cuff (similar; similar)
phone case: H&M (great dupe; similar)
bag: Tory Burch Robinson pebbled square tote (similar)
luggage tag (on bag): J.Crew anchor embossed bag tag (similar)
shoes: Nine West Shindig (similar; similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (similar; similar)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
sweater: Polo Ralph Lauren cable wool cashmere poncho (similar; similar)
top: J.Crew Factory long-sleeve stripe boatneck tee in oat navy spring - sz XS (sold here - $29.50)
skirt: J.Crew mini skirt in fringy lace - sz 0 (sold here - 30% off w/code LOTSTOSHOP)
bag: Longchamp large Le Pliage (sold at Nordstrom / Bloomingdale's)
shoes: H&M suede ankle boots (similar - 40% off; similar - 50% off)

sunglasses: Ann Taylor Lakeside sunglasses (similar; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
shirt: J.Crew Factory infinity shirt (similar - 40% off w/code WEARNOW; similar - on sale)
dress: Gap double-layer linen-cotton dress - sz XS (this season's sold here - extra 40% off w/code MORE)
watch: The Horse Original watch in rose gold/blush (sold here; similar - on sale; similar)
phone case: H&M (great dupe; similar)
bag: J.Crew Downing tote (great dupe; similar; similar - on sale)
shoes: H&M suede ankle boots (similar - 40% off; similar - 50% off)

sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
jacket: Massimo Dutti nappa biker jacket (similar - 35% off; similar)
shirt: Old Navy classic plaid flannel shirt in black watch (similar - 30% off; similar - on sale)
jeans: Articles of Society Mya skinny jeans in Tahoe (other washes sold here)
phone case: H&M (great dupe; similar)
bag: Nina Ricci small Marche in gris (sold here - 40% off; rent; similar; similar)
shoes: Manolo Blahnik gray suede BB pumps in 70mm (sold at Nordstrom / Barney's; similar - on sale)

sunglasses: Ann Taylor Lakeside sunglasses (may still be in stores; similar - $15)
lips: MAKE UP FOR EVER Rouge Artist Natural in N9 (sold here)
necklace: Ann Taylor pearlized stone statement necklace (similar - on sale; similar)
top: Zara lace top with frilled sleeves - sz XS (sold here)
phone case: H&M (great dupe; similar)
pants: MICHAEL Michael Kors stretch ankle pants in new navy - sz 0P (sold here; similar)
bag: Tory Burch Robinson pebbled square tote (similar)
shoes: J.Crew Colette d'orsay pumps in leopard calf hair - TTS, sz 6 (may still be in stores; similar - 50% off; similar - 40% off w/code SHOP40)