My Go-To Winter Date Outfits | 5 Date Night OOTD Ideas!

Hey, everyone! 💗 I hope that you’re having a great day! This weekend, I visited my grandma and hung out with family. Also, on Friday night Alejandro and I went out on a lovely winter date night — dinner and a movie! It got me thinking about how it can be a bit of a struggle to pick out outfits for date night, especially during winter. That’s when a blog post idea came to mind!

These are some of my favorite winter date outfits that are perfect for the season. They’re cute AND cozy, which is definitely necessary for the cold winter air. Keep in mind that since these are my “go-to” outfits, most of them will be from last season. I’ve done my best to find outfits that are comparable and provided links for you if you’re interested in any of the outfit ideas! ❄️

Winter Date Outfit Ideas

1. Romantic Candlelit Dinner.

Velvet skater dress & heels. Pair it with a trench coat & you’re  effortlessly elegant.

Ah, my personal favorite. I love the look of a skater dress. It’s definitely a classic silhouette and very comfortable, which is important for me on a dinner date.

I also adore the velvet texture–it’s perfect for the wintertime. I bought my dress at a boutique in Bloomington, IL and instantly fell in love. The fabric of a velvet dress is warm and thicker in terms of material but it won’t make you feel like you’re breaking a sweat by the end of the night.

This outfit will capture your special someone’s attention, right in time for Valentine’s Day! 💞

2. A Day Out on the Town

Turtleneck midi sweater dress. Pair it with an oversized peacoat and boots. An absolutely stunning look!

I feel sexy while I’m wearing this dress, and this is coming from someone who is a self-proclaimed “awkward turtle.” This is actually Alejandro’s favorite look because he likes the simplicity and feel of the dress.

Originally, I bought my dress at Marshalls and tried to find the same dress for you but had no luck. I ended up finding a very similar dress at Rue 21 on their website.

For this look, I throw on a peacoat, boots, (and nylons, depending on how cold it is outside). I LOVE earthy tones and find that adding a camel or brown coat brings a little bit of warmth to the outfit.

If you want to stay true to wintery cool tones, I recommend choosing a black dress (great for any season) as the centerpiece of your outfit. You’ll be ready for a day in the city! 🌆

3. Netflix & Chill or Movie Night!

Sweatshirt, yoga pants or leggings, and your favorite comfy shoes.

When I go to the movies or am about to binge watch a whole season of Stranger Things, comfort is my number one priority. I still want to look cute for my beau though, so I dress my sweater up with tighter fitting yoga pants or leggings.

PINK isn’t necessarily a store I shop at often because it can be pricey, but I bought this sweater a few years back and still wear it to this day for movie dates. I love cuddling up to Alejandro while wearing the sweater!

On their website, PINK has a very similar ruby sweater. It looks SO cozy! I also found some leggings that look really adorable and comfortable!

4. Coffee Date

Oversized sweater, bralette, and leggings. Pair your outfit with some knee high boots and a puffer jacket!

Alejandro and I go out for coffee a LOT so this outfit is close to what I typically wear on a daily basis. Comfort is always kept in mind but the outfit is pretty versatile and works for many daytime dates.

As I sip my coffee and chat with bae, I feel pretty darn chic! My sweater is from Forever 21, my bralette is from Kohl’s and my leggings are from Aeropostale (I found similar items on their websites). Everything is reasonably priced, which is vital as a recent college grad. You’ll look super fashionable on a realistic and affordable budget!

5. Bonus Outfit: Party it Up!

Glittery sweater dress. Pair it with some heels or pumps.

Are you and your s/o going to a party soon? Since it’s wintertime, I’m going to recommend a sweater dress for a night out. (Yes, I can’t get enough of the sweater dress look!)

I don’t know what it is about this look, maybe it’s the cute and cozy combo that I adore so much. During college, I hated wearing uncomfortable dresses at parties. A sweater dress always kept me warm (which is most important on a winter night) and looked stylish.

The glitter “dresses” up the dress, no pun intended! I actually found a gorgeous glittery sweater dress on Charlotte Russe’s site that would look lovely at any party. Even better, it’s on sale! Add some pumps or heels and you’ll be turning heads all night!

Did you like these winter date outfit ideas? Which outfit was your favorite? Also, what is your go-to outfit for a day or night out with your s/o? Please feel free to comment down below! I love chatting about this topic — it’s so much fun! 💛