Four {Expert Approved} Winter Date Outfit Ideas

You may remember, but back in September, my friend Emily Holmes Hahn (match-maker extraordinaire + dating guru – she’s the founder of white glove matchmaking service, LastFirst) shared four expert-approved date night outfits. The post received a really fantastic response from you guys… and I personally found it really helpful as well as I always struggle with what to wear on a date.

I am so excited to tell you that she is back today for round 2 with four more great winter date-night looks (be prepared to want everything she found… I love it all!!! A big thanks to Emily for putting together these outfits… and to Kelly for tracking down some really cute “look for less” options! Happy Friday friends, I hope you have fun plans (and maybe a date or two that you can wear one of these looks to!) From a downtown dinner to ice skating, these are all such cute ideas!

Date Night Outfit Ideas - What to Wear to a Downtown Dinner Date! Emily Holmes Hahn, Last First NYC - for The Stripe Blog

“For a downtown dinner date this time of year, start with a flattering pair of skinny leather or dark denim pants. Add a shoulder-baring velvet top like this one from ASOS to make the look flirtatious but still wintery. Finish the outfit with dainty jewelry and one of Clare V’s patterned flat clutches – the bolder your choice, the more your outfit will ‘pop’!” – Emily

Downtown Dinner Date: Topshop Moto Jacket // ASOS Blue Drape Top // Drop Earrings // Catbird Cat Ring // Catbird Hammered Rings // Rag & Bone Leather Pants // Gianvito Rossi Booties // Clare V Clutch

Look for Less: Jacket // Pants // Heels // Clutch

Date Night Outfit Ideas - What to Wear to an Uptown Dinner Date! Emily Holmes Hahn, Last First NYC - for The Stripe Blog

There’s nothing more sultry than a little red dress on date night, and this one by Are You Am I has the perfect silhouette and texture, with a nod to lingerie. I balanced it with heavier seasonal accents, like this blazer with velvet details, glossy croc effect bag (the varying reds look so cool together!) and suede OTK black boots.” – Emily

Uptown Dinner Date: Elizabeth & James Velvet Blazer // Are You Am I Slipdress // BaubleBar Tassel Earrings // BaubleBar Lariat // Crystal Ring // Elizabeth & James Croc Print Bag // Stuart Weitzman Highland Boots 

Look for Less: Dress // Jacket // Boots // Bag


Date Night Outfit Ideas - What to Wear on an Ice Skating Date! Emily Holmes Hahn, Last First NYC - for The Stripe Blog

“For this look, I chose a simple all-black ‘base’ layer and added sporty outerwear to appeal to the date’s active nature. This look transitions easily from ice rink to après-skate, too. Once you get inside and have a drink in your hand, you can remove the outer layers to reveal a playful date-night look, complete with adorable slush-proof rubber heels by Hunter.” – Emily

Ice Skating Date: Eugenia Kim Headband // Heart & Star Earrings // White Moncler Cardigan Jacket // Black Crop Top // J.Crew Reversible Shearling Vest // Illesteva Sunglasses // M.Z. Wallace Tote Bag // Hunter Socks // J.Crew Leggings // Hunter Heeled Booties // Hunter Boot Socks // Rag & Bone Cashmere Scarf

Look for Less: Headband // Jacket // Vest // Top // Leggings // Boots // Tote

Date Night Outfit Ideas - What to Wear to a Corporate Holiday Party Date! Emily Holmes Hahn, Last First NYC - for The Stripe Blog

Try to stand out from the drab uniform of a corporate holiday party with a fierce metallic look like this one.  I started with a jumpsuit from Topshop, and added jewel-toned accessories for a luxurious, eye-catching look. I especially love the sexy little accents to this outfit: the thick velvet choker, and the exposed-seam black tights.” – Emily

Corporate Holiday Party Date: Are You Am I Velvet Choker // Topshop Gold Romper // Diane Von Furstenberg Sequin Clutch // Green Heels // Back Seam Tights // Marni Ring

Look for Less: Choker // Clutch // Heels

Leave a Comment


  1. C says 12.9.16

    The first three looks are great! But I would never recommend the 4th for a corporate holiday party – way too much skin! A blazer would make it a little more appropriate, but I think at most workplaces, you really do want to err on the conservative side, particularly as someone’s date.

    • graceatwood says 12.9.16

      I would agree with you! I tend to dress a little bit more conservatively and would personally most definitely add a blazer and make sure the tights are really opaque. That being said I think it probably depends on the company.

    • Emily Holmes Hahn says 12.9.16

      Totally agree too, depending on the company! The Elizabeth and James blazer in the second look is so versatile, it would be perfect with this outfit! xEHH

  2. Brittany says 12.9.16

    dang, these are pretty hot looks!
    i love that red dress.

    xo, brittany
    i’ve got pretty wishlists for mama & babe on my blog today

    • graceatwood says 12.9.16

      I know, me too – it’s so pretty!!! Thanks for stopping by, Brittany – have a great weekend! xo