What to Wear on a Date When It's Freezing Outside

7 Cute Date Outfit Ideas For When Itis Freezing Cold Outside.

It is never easy to figure out what to wear on a date. How many times have you looked at your closet before one and thought to yourself that you literally have nothing to wear? It makes no difference if you just went shopping. Dressing for a date during the winter is even more of a challenge. You cannot just throw on a dress and heels and go out the door. It is never sexy to look like an icicle. If you’re in need of some inspiration, we’ve got you covered.

Here are date night looks that will work for the cold weather:

1. Brunch Date

Brunch dates are usually more casual affairs. If you like to wear dresses, a sweater dress is casual (and warm!) enough for the occasion. Make it look polished with patterned tights, over-the-knee boots, and a pastel coat.

Get the look:

  • Neiman Marcus Callie Leather Wing Bag ($64, Last Call)
  • Kendra Scott Carly Mother of Pearl Stud Earrings ($34, Last Call)
  • Nestled Up Sweater Dress ($52, Tobi)
  • Embellished Bracelet Trio ($16, American Eagle)
  • Hue Chevron Stripe Tights With Stirrup Straps ($13, Nordstrom)
  • Oversized Wool Coat ($120, Mango)
  • Sam Edelman Elina Suede Over-the-Knee Boots ($125, NET-A-PORTER)

2. Movie Date

You may be sitting in a dark movie theater for the majority of your date but you still want to look nice. A pair of wide-leg pants and a blouse are dressy but comfortable enough that you won’t be fidgeting for the whole two hours.

Get the look:

  • Hinge Handle Large Tote ($90, River Island)
  • Quilted Leather Gloves ($58, Pixi Market)
  • Melissa McCarthy Seven7 Plus Shirred Back Blouse ($67, Lord & Taylor)
  • Hakka Inside Zip Boots ($90, Topshop)
  • Kate Spade The Right Stripe Stud Earrings ($58, Zappos)
  • French Connection Velvet Palazzo Trousers ($88, John Lewis)
  • Jessica Simpson Plaid Belted Wrap Coat ($180, Macy’s)

3. Dinner Date

You never know if the restaurant you are going to is going to be toasty warm or not. A layered look is the way to go. Wear a furry vest with your favorite pair of leather leggings and a blouse.

Get the look:

  • Sam Edelman Kourtney Booties ($90, Nordstrom)
  • Clean Zip Fold-Over Clutch ($34, Missguided)
  • Hand Made Coat ($169, Zara)
  • Open Metal Cuff ($12, Sole Society)
  • Peter Long Faux Fur Gilet ($85, Topshop)
  • Premium Buttoned Silk Blouse ($100, Mango)
  • Francisco Faux Fur Leather Blocked Leggings ($148, BCBG)

4. Formal Date

If you are going out somewhere fancy, you normally would go for a dress, right? You could wear a long-sleeved dress, but a skirt and blouse offer more versatility. Pair them with a furry jacket and dressy booties.

Get the look:

  • Inc International Concepts Avalon Minaudiere ($67, Macy’s)
  • Halston Heritage Betty Ankle Strap Booties ($198, Bluefly)
  • Bar Lii Cropped Faux Fur Coat ($110, Macy’s)
  • Olivia The Wolf Golden Flower Hair Pins ($83, ASOS)
  • Sophie Kah Lace Embellished Peasant Blouse ($249, Barneys)
  • Alice + Olivia Kamryn Print Chiffon Maxi Skirt ($160, NET-A-PORTER)

7 Cute Outfit Ideas For When You’re Going On A Hot Date, And It’s Freezing Outside

Cute Date Outfit Ideas For When It's Freezing Cold Outside

I do not know where you are sitting and reading, but let me tell you, it is freezing here in New York as I write this. We’re all running around, pretending to be capable of productivity, grumbling in our big puffy coats about how we’re so tough when in reality, we all want to simply migrate to Los Angeles for the winter. And yet, the show much goes on, as must your dating life! That’s why this question from a reader regarding what to wear on a date in winter felt like the absolute perfect thing to write about today.

Natalie writes:

I’m a long-time reader and commenter, and I wanted to suggest an article for completely and totally selfish reasons…

I have a date tomorrow night I am very excited about, but it’s going to be a nasty cold. I was wondering if maybe The Gloss could do an article with cute date outfits for the freezing cold? Skirts/dresses are my normal go-to, but I don’t even know if tights will help in this situation (might for it anyway). For you know, dinner walks from the Metro/subway to dinner, drinks…. boring date activities. I need inspiration!

First of all, congrats on actually still going on a date! When it’s winter and literally freezing outside, it can be hard to get yourself motivated enough to do something other than hanging with your cats under three blankets. Picking a first date outfit is stressful enough, but figuring out what to wear when you need to balance the desire to look good without sacrificing a couple toes to Jack Frost can be very, very tough.

(Related: The 16 Most Awkward Things That Happen When You’re Binge Dating)

Whether you are single or booed up, you can look special on your next wintertime date! Here are five outfit ideas that will hopefully help.

1. Coffee Date

When you don’t feel like getting all dressed up and just need a solid outfit for a full day’s wear, this look is perfect. Layer a blue chambray shirt with a mustard yellow sweater and skinny jeans. Add a bold statement with a blue trapper hat and keep the rest of the look simple with thin, geometric jewelry, rosy cheeks, and brown boots.

2. Sexy Party Date

Y’all know how I feel about evening jumpsuits by now, right? Because I am truly obsessed with them (I even wore one for New Year’s Eve and every party of the season). Pick a sexy yet comfortable black jumpsuit and wear long socks underneath a pair of cool funky boots. Add a couple of intriguing accents, such as a large colorful ring and a wide headband.

3. Trendy Restaurant Date

Call it spaghetti Western chic! You get to wear a skirt, a crop top, a stunning long coat, and layer on a ton of accessories while still looking lovely. Pop on a pair of black lace-up boots, a warm scarf, and the perfect hat. By the way, out of all these outfits, this is my fave. If you happen to try it out, pretty please snap a photo!

4. Going Dancing Date

When you’re trying to make a big impact using a deep, wintery color palette, it’s often good to stick to just two shades with a sleek silhouette and minimal accessories. And hey, just because it’s freezing doesn’t mean you have to give up on dresses! You just have to pair them with pants in a cute, non-90s way. Wear a short, thick black dress with black leather pants and a chic black coat. Add color into the look with a pair of burgundy booties, the perfect clutch, and a swipe of deep oxblood lipstick. I recommend you just use BB cream, a touch of blush, and black mascara to avoid getting a streaky look if you plan on dancing (i.e., sweating).

5. Barhopping Date

For those of you who like to jump between several different bars on the weekends, you need an outfit with a few layers and multiple warm accessories. Start with a dark red sweater, perfect for disguising any stains one might accrue in the aforementioned bars, and some nice black leggings. Pop on a deep scarlet coat, a super soft beanie, and long, thick gloves to keep everything warm. Keep it casual and comfy for walking with black lace-up shoes.

6. Wine & Cheese Date

For a classy little wine bar, pick a thick knit dress in a dark shade and, instead of wearing simple gray tights, pick gray leggings that are intended to perform well in the cold. Wear a thick neutral-colored coat over the look plus a pair of navy boots and a brown hat.

7. Simple Bar Date

Keep it simple with this cute, chic outfit featuring a sweater over a blouse and black jeans. Keep your feet warm and dry with the perfect tall black boots. Finish the look with silver jewelry and a black beanie.

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