Affordable Winter Date Night Outfits

I can’t believe that Valentine’s Day is only a little over a week away! Normally my boyfriend and I like to grab a nice dinner on or around Valentine’s Day and I like to dress up a little when we do that. The issue tends to be that February 14th falls right smack dab in the middle of winter in Wisconsin. The weather is usually bitterly cold which doesn’t lend well to having a hot date night. If you have ever experienced a Midwest winter, you know that dressing cute in the frigid temps is something that is easier said than done. That is why I wanted to share some affordable winter date night outfits. All of these complete looks are under $300 and most all of the pieces can be easily re-styled for everyday wear because how wasteful would it be to spend a couple of hundred bucks on an outfit that you’re only going to wear once?! So without further ado, here are 5 affordable winter date night outfits. 

Black Dress and Teddy Coat – $199

I have shared this outfit before, but I thought that the color of this coat plays perfectly into Valentine’s Day! So, I wanted to include it here as well. The black dress that I am wearing here is super comfortable. It can also be easily dressed down for a casual look. I have also worn it belted with camel-colored over the knee boots. You could do that as well with the jacket layered on top.

Pom-Pom Sweater and Plaid Skirt – $192

I shared how to take this sweater from day to night in my previous blog post. I wanted to share this look again here because it was one of my favorite night-time looks from the last post. The pom-pom details on this sweater add a cute and fun element to this outfit. We have had a fairly mild winter this year, but if it is super frigid outside, add a pair of tights for extra warmth!

Red Sweater Dress and Booties – $105

This is the most affordable and probably the most comfortable winter date night look that I am sharing here. The dress has been going in and out of stock, so I will link some similars as well. I love a good sweater dress because they are warm, cozy, and comfortable while maintaining a fun and flirtatious element. 

Wrap Crop Sweater and Croc Skirt – $191, $280 w/ Coat

What happens when you pair three edgy and flirtatious pieces and throw a cute jacket over them? You get this look! This might be the most expensive look that I am sharing here, but all of these pieces are truly so versatile. There is a croc texture on the skirt which gives it an edgy vibe. The sweater is cropped and exposes your midriff unless you pair a super high waisted piece, such as this skirt, with it. Paired together with the over-the-knee boots, I think you get a sweet yet flirtatious look, making it the perfect date-night outfit!

Floral Skirt and Pom-Pom Sweater – $155

Not gonna lie, this is probably the exact outfit that I am going to wear this year for Valentine’s day. For me, it is one of those looks that make me feel great – like I can take on the world. That feeling is ultimately what I am chasing every time I put together a new outfit. Helping others achieve that feeling is why I even started this blog in the first place. If I can help one person get there by sharing a look that inspired them, I consider this blog a raging success. Unfortunately, this exact skirt was a $7 Ross find. There are a lot of affordable similar options out there though and I have linked to some.

I hope you have enjoyed these affordable winter date night outfits! Following along with other bloggers and influencers is so much fun for me, but many of them share pieces that are WAY out of my price range. I personally think that everyone should be able to dress and feel great regardless of their budget. My main intention with starting this blog was to share great outfits at everyday prices. I hope that I have been able to do that here! If there is an event or occasion that you are in need of some inspo for, let me know! Feel free to drop me a comment here or on Instagram and I will see what I can do to help you out! 

Thank you so much for reading!

♥