5 Valentine’s Day Date Ideas + Charms & Outfits to Match
Valentine’s Day in New York is special and full of amazing things to do. This year, we’re dressing for the activity. We LOVE love, and will take any opportunity to dress up and celebrate! Below, 5 of our favorite Valentine’s Day moods (with outfits + charms to match). Whether you’re planning something romantic, chaotic, or platonic, consider this your styling guide.
Dinner & a Show
A classic for a reason. This is the Valentine’s date that feels intentional but still fun — dinner, a little wine, then walking into a dark theater hand-in-hand.
What to do:
Start with an Upper West Side dinner before the show. Think Cafe Luxembourg for French bistro vibes or Sala Thai for something cozy and low-pressure. From there, head to Broadway or Lincoln Center — ballet, opera, or a play all count.
The outfit:
A textured fuschia top paired with a black midi skirt keeps things elevated without trying too hard. Finished with glossy black boots and a gold sequin shoulder bag for just enough drama.
Charms to add:
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Heart key charm
A charm bracelet that says: romantic, cultured, and absolutely booked.
Exploring the City
This one’s for the couples (or situationships) who hate sitting still. Walking, wandering, stopping for snacks, accidentally ending up in a different borough — that’s the date.
What to do:
Start downtown and let the day unfold. Grab coffee, walk across a bridge, pop into a museum, explore underrated neighbourhoods like Queens for dinner. No strict plan, just vibes.
The outfit:
A red button up short sleeved top layered over leopard pants — playful, bold, and very New York. Add red sunglasses, this Gucci snakeskin bag, and a baseball cap for that “I live here” energy.
Charms to add:
This bracelet is basically a love letter to the city.
Brunch With Your Galentine
Because Valentine’s Day isn’t just for couples. Sometimes the best date is pancakes, gossip, and your best friends.
What to do:
Meet late (no one is waking up early). Go somewhere buzzy like Sadelle’s, Bubby’s, or your favorite neighborhood spot. Order something sweet and stay way too long.
The outfit:
A satin polka dot button-up with cuffed jeans, pink Mary Janes, and a pink Dooney & Bourke croc bag — polished but playful.
Charms to add:
A charm stack that celebrates friendship, femininity, and ordering dessert twice.
Jazz Club Date Night
Low lighting, a strong drink, live music, and the feeling that you’ve stepped into another decade. This is a Valentine’s date that’s intimate without being loud — perfect for leaning in close and staying out late.
What to do:
Book a table at a jazz club or piano bar. Order something classic (martini, old fashioned, espresso martini) and let the music set the pace. No phones, just connection.
The outfit:
A knit tank with red rose details paired with a dark midi skirt keeps things sultry but unfussy. Finish with classic knee-high boots, this elevated YSL little black bag with a chain detail.
Charms to add:
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Music note charm
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Horseshoe charm
A charm bracelet that whispers: late nights, jazz records, and very good taste.
Solo Shopping Date
Because sometimes your Valentine is your debit card — and honestly? She’s loyal.
This is the date for wandering vintage stores, popping into bookstores, trying on things you don’t need, and getting a little treat just because.
What to do:
Spend the afternoon hopping between your favorite shops — vintage, indie boutiques, maybe a charm bar stop at The Niche Shop ;) Take breaks for coffee, window shop with no urgency, and let yourself linger. Shopping is so much more fun when no one’s rushing you!
The outfit:
A romantic floral blouse paired with a pleated mini skirt feels flirty but effortless. Add studded Mary Janes for comfort (but make them fashion), a chic red handbag, like this Prada one.
Charms to add:
A charm bracelet that says: main character energy, self-love, and a successful shopping day.
Whether you’re planning dinner plans, city wandering, or a Galentine’s brunch, your outfit — and your charm bracelet — should feel personal. 💘
Shop the looks and charms in-store and online.
