What To Wear To Get A Second Date: 10 Hot Outfit Ideas

You have a date. Step 1: Congratulate yourself on your active romantic life. Step 2: Panic about what to wear. If this process sounds familiar, we sympathize and are here to help. While date night dressing may seem complicated, we believe we’ve got it down to somewhat of a science. It’s all about striking the right balance.

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  • To see what we mean, click through four detailed examples and a handful of outfit ideas that you can stick in your back pocket, so next time your date tells you they’re inconveniently early, you can confidently breeze out the door in snap.

  • Peaches Geldof
    Photo credit: Daniel Deme/WENN.com

    1. Balance Sweet & Tough

    Crafting the perfect date night look boils down to one tenet: balance. Not too sexy, not too sweet; not too revealing, not too covered up. You get the point. At a TK Maxx store opening in London, Peaches Geldof demonstrated her grasp of the concept by pairing ladylike slingbacks and a print dress with an edgy moto jacket.

  • Street Style
    Photo credit: Stockholm Street Style

    2. Show A Little (Unexpected) Skin

    While there’s nothing wrong with highlighting your legs or décolletage, we’re fans of revealing skin in less predictable ways. Try baring your shoulders, wearing a low-back top, or showing a sliver of stomach like this stylish civilian did.

    Image from Stockholm Street Style

  • Rosie Huntington-Whiteley
    Photo credit: Donato Sardella/WireImage

    3. Dress Up Your Jeans

    At the Isabel Marant BBQ in Los Angeles, Rosie Huntington-Whiteley demonstrated a crucial date dressing rule: strike a balance between casual and dressy. Note how the model and actress tempered her sequin Isabel Marant Ecru Glowy Jacket ($4300) and pumps with relaxed denim (all by the designer).

  • Chiara Ferragni
    Photo credit: Joe Schildhorn /BFAnyc.com

    4. Say Yes To Lace

    Is there a more romantic fabric than lace? We think not, and are all for its appearance on date night. To pull it off, take note on how Chiara Ferragni of The Blonde Salad’s Louis Vuitton frock she wore for a screening of Mademoiselle C is high-necked and long-sleeved. The more modest cut is still alluring, but leaves a little to the imagination.

  • Zina Charkoplia
    Photo credit: Fashion Vibe

    5. Tried & True Combo: Sexy + Grungy

    By itself, Fashion Vibe blogger Zina Charkoplia’s Zara slip dress might read lingerie-like, but when toughened up with a plaid button-down (also Zara), the effect is enticing, but not over the top. Tying a flannel around the waist is also strategic for adding shape to a loose-fitting frock.

  • Whitney Port
    Photo credit: Astrid Stawiarz/Getty Images

    6. Make The Most Of All Black

    Black doesn’t have to be boring. Whitney Port gave her noir ensemble a date-appropriate spin with skinny leather pants and lace-up stilettos at the SHOW Beauty launch in New York City.

  • Irina Lakicevic
    Photo credit: A Portable Package

    7. Pair Micro With Oversized

    Forgive us for elaborating on the rule of balance, but the concept also applies to proportion. Want to wear a leather miniskirt like Irina Lakicevic of A Portable Package did? No problem, just pair it with an oversized piece, like the blogger’s vintage Valentino blazer.

  • Street Style
    Photo credit: Stockholm Street Style

    8. Fail-Proof Pair: Moto Jacket & Mini Skirt

    If you’re ever completely stumped on what to wear, fall back on the trusty combination of a motorcycle jacket and flirty mini skirt. The look is one part tough, one part alluring, and wholly perfect.

    ‚ÄčImage from Stockholm Street Style

  • Miroslava Duma
    Photo credit: Billy Farrell/BFAnyc.com

    9. Paneled Dresses Are Your Friend

    We weren’t all blessed with hourglass figures, but thanks to side-paneled dresses we can at least fake it. Notice how Miroslava Duma’s printed frock creates the appearance of curves? A pair of Prada platform heels, like Duma’s, never hurt either.

  • Aimee Song
    Photo credit: Song of Style

    10. Hit The Metallics

    Try this: take one party-ready metallic piece, in this case, Aimee Song of Song of Style selected Zadig et Voltaire gold pants, and add a skin-baring basic, such as Song’s Helmut Lang wrap top. It’s an easy formula for looking subtly dressed up, and pairs well with the neutral staples you likely already own.

  • For Love & Lemons Exclusive Pirouette Dress ($135)

  • Rachel Zoe Angie Silk Blouse ($225)

  • Elizabeth & James Northern Star Lariat Necklace ($250)

  • Reformation Iceland Jacket ($288)

  • Smashbox MegaTint Long Wear Lip Color ($20) in Whirl

  • Alexander Wang Lovisa Ankle Strap Pumps ($645)


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