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Valentine’s Day is the perfect time to draw a little inspiration from the leading ladies of our favorite romantic comedies. From whimsical and nostalgic to classic and chic, these looks capture the essence of each film while giving you modern style moments that feel effortlessly wearable. Whether you’re celebrating love, friendship, or yourself, these outfits will have you looking like the star of your own rom-com.
1. Retro & Fun: Inspired by The Wedding Singer
Add some '80s flair to your Valentine’s Day look with a playful multicolor stripe sweater paired with mid-rise straight jeans that are comfy enough to dance the night away. A washed denim frill detail jacket adds a touch of vintage cool, while classic contrast lace-up sneakers keep it casual. Finish with a polka dot padded knit beanie and a floral jute crossbody bag for quirky charm. Accessorize with a triple pendant necklace and simple silver hoops to bring a little romance to your retro-inspired outfit. Perfect for a night of karaoke or a retro-themed date!
Multicolor Stripe Sweater + Washed Denim Frill Detail Jacket + Risen Elastic Band Mid Rise Straight Jeans + Polka Dot Padded Knit Beanie + Multi Painted Floral Jute Crossbody Bag + Classic Low Top Lace Up Contrast Sneakers + Triple Pendant Necklace + Metal Texture 20mm Hoops
2. Whimsical & Regal: Inspired by The Princess Bride
Step into your fairytale moment with a patchwork washed denim overall maxi dress that feels straight out of a dreamy meadow. Layer it with a soft round-neck gold button cardigan to keep cozy. Oceanline braided double-strap flat sandals add a modern touch, while a stitching embossed large-capacity backpack bag brings practicality with a hint of charm. Finish with a cross multi-charm pendant necklace and filigree flower & pearl drop earrings to channel Buttercup’s elegance in a contemporary way. This look is perfect for a romantic picnic or a stroll through nature.
Patchwork Washed Denim Overall Maxi Dress + Round Neck Gold Button Cardigan + Oceanline Braided Double Strap Flat Sandals + Stitching Embossed Large Capacity Backpack Bag + Cross Multi Charm Pendant Necklace + Filigree Flower & Pearl Drop Earrings
3. Relatable & Charming: Inspired by Bridget Jones’s Diary
Cozy and relatable, this outfit has Bridget’s charm written all over it. Start with a geometric colorblock stripe mock neck sweater for a pop of personality, and tuck it into dark wash straight-leg jeans for a flattering fit. A slim black bow buckle belt adds polish, while a brown leather bow accent backpack bag is practical yet stylish. Accessorize with pave crystal pearl stud earrings and a crystal heart fit-together necklace for subtle romance. Whether you’re heading out with friends or cozying up at home, this look is as warm and lovable as Bridget herself.
Geometric Colorblock Stripe Mock Neck Knit Sweater + Bow Buckle Women’s Slim Black Belt + Risen Straight Leg Mid-Rise Dark Wash Jeans + Be Bold Jotter Gel Pen Set + Brown Leather Bow Accent Backpack Bag + Crystal Heart Fit-Together Necklace + Pave Crystal Pearl Stud Earrings + Wavy Large Hair Claw Clip
4. Playful & Nostalgic: Inspired by 13 Going on 30
Channel Jenna Rink’s fun and flirty vibe with a pink stripes bow-embellished dress that screams youthful charm. Pair it with pink lace sneakers for a casual twist, and accessorize with metal bow stud earrings and a dainty wired bow gold-dipped necklace. To complete the look, carry a quilted floral print midi makeup bag filled with goodies: a watermelon rosewater grapefruit sheet mask, strawberry matcha latte depuffing eye patches, roll-on perfume in No. 9 Cassis, Poppy & Pout birthday cake lip balm, and a folding heart air cushion pocket comb. Perfect for a Galentine’s Day brunch or a fun night out!
Pink Stripes Bow Embellished Long Sleeve Dress + Metal Bow Stud Earrings + Dainty Wired Bow Gold Dipped Necklace + Quilted Floral Print Midi Makeup Bag + Watermelon Rosewater Grapefruit Sheet Mask + Strawberry Matcha Latte Depuffing & Hydrating Eye Patches + Roll-On Perfume No. 9 Cassis + Poppy & Pout Birthday Cake Lip Balm + Folding Heart Air Cushion Pocket Comb
5. Cozy & Classic: Inspired by You’ve Got Mail
Kathleen Kelly’s timeless NYC style translates beautifully to Valentine’s Day with a soft mock neck knit top layered under a cozy denim pocket knit cardigan. Pair it with hi-rise wide-leg jeans for a relaxed but polished silhouette, and add western buckle raffia mule clogs for a little vintage-inspired flair. Finish the look with embossed leather and vintage metal hoops, a large capacity brushed suede bag, and the I Freaking Love You soy candle for a touch of charm and humor. Perfect for coffee dates, bookstore browsing, or just curling up with your favorite rom-com.
Soft Mock Neck Long Sleeve Knit Top + Denim Pocket Knit Cardigan + Kut from the Kloth Hi-Rise Fab-Ab Wide Leg Jeans + Western Buckle Raffia Mule Clogs + Embossed Leather & Vintage Metal Hoops + Large Capacity Brushed Suede Bag + I Freaking Love You Soy Candle
Your Rom-Com Wardrobe Awaits
These Valentine’s Day outfits take inspiration from some of the most beloved romantic comedies, blending nostalgia with modern flair. From whimsical overalls to playful pink dresses, these looks let you channel the charm of your favorite leading ladies. No matter where your Valentine’s Day takes you—coffee dates, karaoke nights, or a cozy evening in—there’s a rom-com-inspired outfit ready for your love story.