date outfit winter skirt gifI 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 go 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 its going to be 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 the 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

Yellow and blue
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 (Isabel Marant Etoile Sade Light Blue Chambray Shirt, Harvey Nichols) with a mustard yellow sweater (Damned Delux Cesca Knitted Jumper, The Hut) and skinny jeans (J Brand Mid-Rise Skinny Jeans, Style Bop). Add a bold statement with a blue trapper hat (Imposter Faux Fur Trapper Hat, Barneys) and keep the rest of the look simple with thin, geometric jewelry (Cutout Geo Statement Necklace, Forever21), rosy cheeks (Benetint, Sephora), and brown boots (Lace-Up Combat Boots, Wet Seal).

2. Sexy Party Date

Jumpsuit winter date outfit

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 annnnd every party of the season). Pick a sexy yet comfortable black jumpsuit (Givenchy Crepe De Chin Jumpsuit, Far Fetch) and wear long socks (Sheer Knit Over The Knee Socks, Express) underneath a pair of cool funky boots (Iro Keira Suede And Leather Boots, YouHeShe). Add a couple of intriguing accents, such as a large colorful ring (Silver Blue & White Cubic Zirconia Ring, Ice Online) and a wide headband (Eugenia Kim Chiara Knotted Metallic Headband, Intermix).

(Related: The 20 Sexiest Tried-And-True Perfumes That You Need To Pick Up For Date Night)

3. Trendy Restaurant Date

Black and green

Call it spaghetti Western chic! You get to wear a skirt (La Diva Pleated Maxi Full Skirt in Green, ChicWish), a crop top (Pierre Balmain Printed Silk Crepe De Chine Shirt, The Outnet), a stunning long coat (Jacques Vert Long Faux Fur Collar Coat, John Lewis), and layer on a ton of accessories while still looking lovely. Pop on a pair of black lace up boots (Rawlings Black Suede, Steve Madden), a warm scarf (Light Grey Cashmere Knitted Scarf, Black), and the perfect hat (Gabrielle Hat, Need Supply). 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

Black dress with burgundy

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 (Bead The Grace Wool Blend Dolly Dress, Chicwish) with black leather pants (DKNYC Plus-Size Faux Leather Tuxedo Strip) and a chic black coat (Nolita Crepe Coat, Coast). Add color into the look with a pair of burgundy booties (Pasionn Boots, Steve Madden), the perfect clutch (Franklin Classic Envelope Clutch, Monsoon), and a swipe of deep oxblood lipstick (Tom Ford Beauty Lip Color in Bruised Plum, Neiman Marcus). 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).

Click to the next page to see the perfect look for barhopping, the best style for a wine and cheese night, and a great look for transitioning into a date from work!

5. Barhopping Date

Burgundy date outfit
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 (Therapy Cable Jumper, House Of Fraser), perfect for disguising any stains one might accrue in the aforementioned bars, and some nice black leggings (Nike Leg-A-See Legging, Office). Pop on a deep scarlet coat (Wine Red Lapel Long Sleeve Knit Coat, Choies), a super soft beanie (Loma Georgia Cashmere Beanie, The Outnet), and long, thick gloves (Wool Leather 3/4 Length Gloves, Jaeger) to keep everything warm. Keep it casual and comfy for walking with black lace-up shoes (TOMS Lace Up High Top Sneakers, Bloomingdale’s).

6. Wine & Cheese Date

Navy dress with Brown

Navy dress with Brown by sam-escobar featuring a blue dress

For a classy little wine bar, pick a thick knit dress in a dark shade (Kaliko Blue Ponte Dress, House Of Fraser) and, instead of wearing simple gray tights, pick gray leggings that are intended to be perform well in the cold (Reebox NYLUX Tights, Zalando). Wear a thick neutral-colored coat over the look (Brown Lapel Long sleeve Knit Coat, Choies) plus a pair of navy boots (Bolder & Boulder Boot, ModCloth) and a brown hat (Bailey Curtis Crushable Fedora Hat, Urban Excess).

7. Simple Bar Date

Winter date outfit 1
Keep it simple with this cute, chic outfit featuring a sweater (Gray Bejeweled Collar Sparkle Sweater, US Trendy) over a blouse (Classic Oxford Cotton Mini Dress Shirt, Net-A-Porter) and black jeans (Petite Super High Waist Jeans, John Lewis). Keep your feet warm and dry with the perfect tall black boots (Frye Melissa Tab Tall, Zappos). Finish the look with silver jewelry (BCBGMAXAZRIA Triple Layer Chain Ring, BCBG) and black beanie (Knitted Hat, H&M).

GIF via Tumblr.