Eight Outfits That You and He Will Both Love

Sometimes the hardest outfit to put together is one that’s interesting but not too interesting— something that’s on-trend enough to impress judgy friends but not so fashion-forward it flies right over boys’ heads (harem pants, shoulder pads and denim tuxedos come to mind).

High Hemline

He'll like the high hemline, while you'll like the graphic print-mixing and perfectly oversize clutch.

SEAMED MINI DRESS, $485, OPENING CEREMONY, SHOPBOP.COM; "BEADS" PRINT CLUTCH BAG, $310, MARNI.COM; PERSONALIZED BRACELET, $50, MIRIAM MERENFELD, MAXANDCHLOE.COM

©Lucky

1 of 9 Courtesy of shopbop.com, marni.com, and maxandchloe.com

Muscle Tank

With a muscle tank, selvedge denim and sturdy yet pretty platforms, this version of the dude-approved jeans, t-shirt and heels combination feels much fresher.

ECRU T-SHIRT, $120, MAJE.COM; "JOYOUS RED" LIPSTICK, $24, NARS, BEAUTY.COM; MATCHSTICK JEAN, $148, JCREW.COM; "BAMBOLA" PUMPS, $300, B BY BRIAN ATWOOD, SHOPBOP.COM

2 of 9 Courtesy of maje.com, beauty.com, jcrew.com, and shopbop.com

High-Low Hemline

tie collar blouse trench coat pleated skirt

The skirt's high-low hemline is like the outfit: simple and a little conservative...but also a teeny bit flirty.

"JESSSICA" LACE TIE-COLLAR BLOUSE, $225, RACHEL ZOE, BERGDORFGOODMAN.COM; "NEW" TRENCH, $500, A.P.C., LAGARCONNE.COM; SHIMMER PLEAT DIP HEM SKIRT, $130, TOPSHOP.COM

3 of 9 Courtesy of bergdorfgoodman.com, lagarconne.com, and topshop.com

Down-to-Earth

How to be the low key, down-to-earth girl and still look put-together.

"MERCI" STRIPE TEE, $49.50, MADEWELL.COM; BRUSHED COTTON TRACK PANTS, $125, JAMES PERSE, NETAPORTER.COM; DENIM CHUCK TAYLOR ALL STARS, $109, CONVERSE, MYTHERESA.COM

4 of 9 Courtesy of madewell.com, netaporter.com, and mytheresa.com

Marilyn

Toughen up the obvious nod to Marilyn Monroe with cagey heels and a bit of punk arrowhead jewelry.

GRECIAN DRESS, $350, L'AGENCE, BARNEYS.COM; "ARRAY" CAGE SANDAL, $299, STUART WEITZMAN, LASTCALL.COM; ARROWHEAD RING, $625, PAMELA LOVE, BARNEYS.COM

5 of 9 Courtesy of barneys.com, lastcall.com, and barneys.com

Low-Heeled Sandals

Simple low-heeled sandals don't feel high-maintenence, while the one-piece swimsuit is sexy and a little more covered-up, too.

DIP-DYE "ACAPULCO" MAILLOT, $220, MILLY, CUSP.COM; COLOR MIRROR AVIATOR SUNGLASSES, $7.50, WETSEAL.COM; 68, STEVENALAN.COM; "NICO" SNAKE LOW HEEL SANDALS, $90, TOPSHOP.COM

6 of 9 Courtesy of cusp.com, wetseal.com, stevenalan.com, and topshop.com

Old Hollywood-Style

sun dress red cat eye sunglasses sandals

Pairing an Old Hollywood-style red dress with a slightly unpredictable, eye-catching shoe makes it way more modern.

50S SUN DRESS, $286.48, BOUTIQUE BY JAEGER, ASOS.COM; CAT EYE SUNGLASSES, $360, TOM FORD, NORDSTROM.COM; "YELENA" SANDAL, $140, SAM EDELMAN, PIPERLIME.COM

7 of 9 Courtesy of asos.com, nordstrom.com, and piperlime.com

Date Night

croc clutch black dress leather biker jacket

An updated spin on the lazy date night staple: asymmetrical black dress, tough accessories and a buttery leather moto jacket.

"RENDEZVOUS" BLACK DRESS, $340, SANDRO-PARIS.COM; SUEDE CROC STUD CLUTCH, $42.97, ASOS.COM; TRIANGLE ARMOR NECKLACE, $150, HOUSE OF HARLOW, NEIMANMARCUS.COM; LEATHER BIKER JACKET, $310, TOPSHOP.COM

8 of 9 Courtesy of sandro-paris.com, asos.com, neimanmarcus.com, and topshop.com