Winter date nights are the perfect excuse to dress up and feel your best, no matter where the evening takes you! Whether you’re planning an intimate dinner at a cozy local spot, a chic night out, or a laid-back ice cream date, your outfit should match the mood and make you feel fabulous.
From elevated looks that add a touch of glam to cozy-casual vibes, I’ve got you covered with the best winter date night outfits for every type of special occasion. Ready to turn heads (or feel amazing in your outfit)? Let’s dive into 18 outfit ideas that are sure to impress!
18 Winter Date Night Outfit Ideas
1. Edgy Elegance: Winter Look
I am turning the original ‘little black dress’ idea into the ‘little black outfit’! This vegan leather skirt is perfect for those chilly winter nights and instantly elevates any look.
2. Chic in Black & Bold
Easily add a pop of color to your winter date night look with this cozy coatigan. For all of my fellow millennials, these skinny jeans are one of my favorites and they look amazing with several style boots and booties!
3. Effortlessly Chic in Neutrals
You can never go wrong with a few neutral basics! This crew neck long sleeve is great as a standalone piece or can be easily layered. Paired with your favorite pair of straight-leg jeans and trendy booties, you will be ready to take on the town!
4. Day-to-Night Style
Now it may not always be ideal to head out for date night straight from work but this style definitely gives you that flexibility! The flirty accent of the mesh bodysuit complements the wide-leg trousers perfectly. Making this a great day-to-night look for any of my busy office gals!
5. Monochromatic Looks
Do you know what the secret is to wearing sweaters over dresses? CLICK HERE to see! Okay but seriously, I love styling sweaters over dresses, especially during the colder months. It’s a great way to utilize pieces you already have in your closet! See more sweater over dresses ideas, HERE.
6. Cozy Cardigan + Dress Combo
I love this color combo, especially for a more laid-back date night this winter. The textured cardigan and the tiered maxi dress add a bit of texture to the entire look! In my opinion, you can never have too many cardigan and dress combos.
7. Elevated Neutral Style
Whoever told you that you can’t wear black and brown together is wrong… you wear whatever you want! This neutral crew sweater layered over a cozy black midi dress makes for the perfect winter date night outfit. It’s the ideal look for dinner and a movie!
8. Timeless Winter Style
Cozy up in this matching long sleeve and skirt set! I love the neutral tone but it’s available in several other colors. It’s the perfect balance between cozy and elevated!
9. Sleek Winter Chic
A winter date night outfit classic is a turtleneck sweater dress paired with your favorite knee high boots! If you are afraid of getting too chilly, you can always layer up with sheer fleece lined tights.
10. Mesh Meets Elegance
Love this look! Don’t let the mesh long sleeve scare you – you can easily layer your favorite winter coat over this without sacrificing style! You could style this with heels if it isn’t too chilly where you live and are feeling brave.
11. Blazer Meets Denim
Add a pop of color and a bit of sophistication to any winter date night look with these blazer! I am wearing an XS and it still has an oversized fit which I love. Perfect for styling with a sweater or laid back tee with your favorite jeans!
12. Satin + Sweater Vibes
Neutral pieces are essential for any winter wardrobe, especially when you can style them for several different occasions. It’s the perfect blend of cozy and chic!
13. Bold and Flirty
Again.. whoever said you couldn’t wear florals in any season but spring and summer is wrong! I love this top not only because it’s bright and colorful but there’s something a little flirty about it. Style with your favorite pair of black jeans OR relaxed blue jeans for a more casual feel.
14. Chic Floral Style
This outfit is perfect for a winter date night—casual but pulled together. The coatigan adds a cozy touch. Finish it off with heeled boots and a cute shoulder bag, and you’re ready for whatever the evening brings!
15. Comfy Casual Look
Looking for a little more laid back look for your winter date night? I have got you covered! This oversized cardigan pairs well with almost anything. I decided to elevate this look a bit with jeans and heeled booties but you could style it with leggings for an even more relaxed look!
16. Boho Winter Elegance
This look is an easy way to stay cozy without sacrificing style. The hoodie keeps things casual and comfortable, while the flowy, printed maxi skirt adds a touch of elegance. It’s perfect for a laid-back winter date night!
17. Edgy Animal Print Look
Leopard pants are making a comeback and I love it! This is certainly a more casual take on the winter date night. You can never go wrong with a fun pair of pants – it’s always a conversation piece. See more ways to style leopard print pants HERE.
18. Simple but Elevated
See winter coats and accessories to complete your winter date night look HERE.
Shop More Winter Date Night Outfit Ideas
