This blog post was put together in partnership with Beachwood Place. All opinions are my own.

Getting ready for date night in winter can be a straight up struggle. First, you have to mentally prepare to thrust yourself into the cold/wind/rain/snow. Then you have to figure out how to look cute in the midst of all of it. [I.E. you have to figure out how to make thicker fabrics and multiple layers look sexy instead of frumpy.]

Trust me, I know it’s not easy. But it can be done! Which is exactly why my husband, Dane, and I decided to partner up with our favorite mall, Beachwood Place, to help you get your creative juices flowing. Scroll down to see a couple of casual winter date night outfits you can easily recreate [or straight up copy].

Casual Winter Date Night Outfits: Look #1:

The more casual look of the two, these winter outfits are perfect for a day date that slides into the evening hours. Obviously, there’s nothing fancy about long sleeve waffle tees, lol. But as you can see they can still look put together!

Dane kept his look simple, yet clean with a pair of light wash jeans and a crisp pair of white Nike’s. And I dressed up my basic tee a bit with a fun pair of platform sneakers and a matching faux leather jacket. While there’s nothing crazy going on here, I do want to point out two things:

1. My thinnest layer is closest to my body, while my thickest layer [the faux leather jacket] is sitting on top of everything else. That was a strategic move on my end. Layering from thin to thick will prevent you from looking frumpy. And keeping all layers on the thinner side will help you out, too.
2. Our outfits are fully pressed and our shoes are scrubbed clean. Both of these things can totally make or break a casual look, so be sure to put in the extra effort if you want to go on a date looking this casual.

SHOP THE LOOKS

[Pro tip for my Cleveland friends! Remember that you can order online and pick up in store at Beachwood Place! And where that’s not offered, just take a screenshot of the product page into the store with you so you can easily find what you’re looking for! I linked the exact stores I bought everything from, but comment here or DM me on Instagram if you have questions.]

Meach’s Look:

*Long sleeve top is a similar top from the same store, The Buckle, as mine wasn’t available online.

Dane’s Look:

Casual Winter Date Night Outfits: Look #2:

While I’m not against busting out a dress in the middle of winter, dressing up jeans can be just as cute. And a whole lot warmer. So that’s what Dane and I did for date night outfit #2.

These looks are perfect for a nicer dinner date, a trip to a wine bar, a comedy show, the list goes on! While you can’t tell in the pictures, Dane’s button up is a thicker fleece material vs. a thin, cold cotton. And my long sleeve black top is layered with a thin suede overcoat. Finding dressier pieces in warmer fabrics is key to achieving both comfort and a more elevated style. To keep your jeans looking dressy, I also recommend:

1. Opting for dark denim vs. light as it’s generally dressier, and even more forgiving. 😉
2. Swapping out sneakers for dress shoes. It won’t kill you, and you’ll be able to bop around to more places. You never know where the night might take you, but if you’re wearing sneakers you’ll likely be limited [a lot of higher end establishments prohibit them].

SHOP THE LOOKS

Again, if you’re in Cleveland, go snag these winter outfits [or something similar] from Beachwood Place! Otherwise, here are the links.

Meach’s Look:

Dane’s Look:

*I linked Dane’s shirt and jeans in two colors each since they were available. 🙂 Options are never a bad thing!

While motivating yourself to actually leave the house might present another challenge, I hope that when you do these cute winter outfits serve to inspire you. And help you to get dressed a whole heck of a lot faster! Because you and I both know, the longer it takes to get ready for a winter outing, the more tempting it becomes to just stay home, lol. 😉

Oh, and PS. If you’re short like me and want to look a little bit taller, this post includes 10 tips to do just that! And this post features some great women’s transitional shoes if you’re in the market.

Thank you from the bottom of my heart for reading. I hope to see you back here again soon.

XX,