Winter Date Night Ideas

As the weather gets colder, the temptation to live in sweatpants, furry slippers and cozy sweaters is hard to resist. This is especially true at night, when finding something both warm and flattering seems an impossible task. But what happens when your favorite guy asks you out on a date? You go out, and you do it with style. Here at Pearl and Clasp we are fervent believers in comfort AND fashion, and seriously recommend choosing an outfit that will keep you warm, comfortable and relaxed so that you can enjoy your evening and all it brings. After all, sexiness is all about confidence! Need some ideas?

Heeled boots. Our favorites are heeled booties, because they look amazing with literally everything: tunics and leggings, black tights, jeans, jeggings, leather pants and basically any other bottoms you can think of. Stilettos say you mean business, and chunkier heels are chic and comfortable. Both will make your outfit great, so make sure you’ve got a pair or two in your closet for this season!


Sweater dresses. Super diverse and easy to wear, sweater dresses are a seasonal must-have that will make date night a breeze. Perfect for day-to-night outfits, sweater dresses look amazing with other layers like leather jackets, blazers or trench coats, as well as colorful accessories, scarves and jewelry. Throw on some tights for added warmth and you’ll be ready to go!

sweater dress

Own the season with cozy-looking knitwear and interesting, touchable textures. Cable knit sweaters, wraps, wool coats, thick scarves and furry accessories will make you look approachable and create a homey atmosphere. If your date is a bit less formal, don’t hesitate to wear your trusty Uggs or blanket scarf! Enhance your outfit with some jewelry and an oversized bag, and add some deep red lipstick for a bit of romance. Tunics, leggings and heeled booties also work well for this laid-back but super stylish look, so pull out your favorite pieces and combine them for an ensemble that’s all your own!

winter date

What are your favorite winter date night styles? Do you know the best way to balance warmth and fashion?

Until next time,



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