Date Style Decoded: Foolproof Outfit Ideas for Every Occasion

With so many things that could potentially go wrong on a first date (everything from awkward eye contact to having literally nothing in common — yikes!), the last thing you should have to worry about is your look. While you obvs want to put forth a decent amount of effort, you still want to play it cool. We’ve decoded *exactly* what to wear, whether you’re heading to a traditional dinner and a movie, spending an evening salsa dancing, or strolling through your boo’s favorite art gallery so you’re not left texting your BFF during the *final* hour for play-by-play fashion advice. Keep on scrolling for 10 foolproof style essentials (think: bustier tops and daytime metallics galore) that are ready to slay.

1. Mini Golf: Don’t let a little date-night hype stop you from having fun (‘cause remember you’re a FUN date). Proceed to channel your playful side with this It girl-approved patchwork co-ord that delivers just the right amount of sex appeal. Brit + Co Pick: Tommy Hilfiger Gigi Hadid Patchwork Top ($128) + Tommy Hilfiger Gigi Hadid Patchwork Print Bodycon Skirt ($188)

2. Dive Bar: You? Shy? Nah. Let ‘em know you’re interested (no. Playing. Games.) with this come-hither floral bodysuit that — dare we even say it — turns all the heads. *As if* you didn’t already know. Oversized hoops and Chelsea boots are mandatory for a trivia night at your favorite dive bar — give or take an epic karaoke throwdown. Brit + Co Pick: Reformation Chandler Bodysuit ($128)

3. Weekday Hangout: Don’t overthink it! For a casual Taco Tuesday outing with your boo, this denim trucker jacket will more than suffice. Between the palm tree embroideries and frayed hem, you’ll never feel like you’re trying too hard again. Just add Chuck Taylors and a pair of your most flattering high-waisted skinnies for a look that’s hella cool (read: No first date jitters here). Brit + Co Pick: Levi’s Ex-Boyfriend Trucker Jackets ($128)

4. Impromptu Meeting of the Parents: Now would be the time to adopt a fancier uniform. See exhibit A: This poplin swing shirt with a fun peplum is a bajillion times more femme (and playful) than any blasé boardroom button-down. The final touch? Neon statement earrings for no shortage of sass. Brit + Co Pick:Kate Spade Poplin Swing Shirt ($168)

5. Candlelit Dinner: Yet another swishy accordion pleat skirt? For date night? Groundbreaking. But not so fast: Before you completely write off this piece de resistance, think about its after-hours appeal. With the right mock-neck blouse and DDG chandelier earrings on standby, you’ll be equipped for anything from a candlelit dinner to a romantic rendezvous. Brit + Co Pick: Stylekeepers Retro Juliette Pleated Skirt ($99)

6. Art Gallery Tour: Take the “modest is hottest” approach with this bow-topped cashmere sweater (in ballerina pink — no less!) that’s practically designed for admiring a room full of Monets. A twirl-worthy pleat skirt and nude steppers will have you feeling like a modern-day Juliet. Brit + Co Pick: Ted Baker Nehru Knit Top ($191)

7. Trendy Cocktail Lounge: You’ve got the first few dates in the books (phew!), and now you’re moving into “officially official” territory. Bring that ba da boom factor with these slick patent leather leggings that look just as good on-duty as off. You best believe an oversized slouchy sweater and sky-high stilettos are in order for drinks by the bar and whatever else the night brings. Brit + Co Pick: Blank NYC Patent Vegan Leather Leggings ($98)

8. Low-Key Saturday Drinks: Run, don’t walk, to snatch up this versatile crepe tuxedo jacket that’s guaranteed to slay at first sight — if nothing else, it’ll keep any lingering nippy temps at bay. For maximum impact, toss it over your favorite LWD or double down with a neck-tie blouse, vintage mom jeans, and velvet penny loafers for a low-key wild card date night. Brit + Co Pick:Wilfred Chevalier Jacket ($225)

9. Dinner and Dancing: As far as this goddess-inspired gathered pleat maxi is concerned, flamenco dancing will be included in the night’s festivities. For a red haute entrance, round out your final rose ceremony-esque look with some red carpet-worthy Swarovski earrings and rose gold platforms. How could anyone say no to that? Brit + Co Pick: Banana Republic Gathered Pleat Maxi Dress ($148)

10. Cocktails to Clubbin’: Sure, you may be single now, but not for long. Show ‘em who’s boss with this metallic fuchsia wide-knot blouse that means serious business and delivers from sippin’ bubbly to late night clubbing. Want more versatility? Pair with a high-waisted pencil skirt and power pumps for post-work drinks or cropped denim flares and backless mules come the weekend. Brit + Co Pick: Staud The Biagio Top ($165)

What are your go-to date night essentials? Follow us on Pinterest for more style tips!

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