Date Night Winter Outfits

Black OTK Boots for Date Night

This Winter, my black over-the-knee (OTK) boots have been my go-to shoes for date night. They have a comfortable 3″ stacked heel so they’re easy to walk in, and since I can wear socks in them and they cover about 60% of my leg, they help keep me warm. But the style itself has some inherent sexiness, so they still add some oomph to an outfit even if all of the other pieces are more cozy than sexy. I’ve rounded up a six ways I’ve worn my black OTK boots for date night, so let’s take a look!

ONE: Cozy Turtleneck Sweater and Jeans

Sweater (c/o) | Jeans (Similar w/ more sizes) | OTK Boots | Similar Bag 

I’ve worn this outfit for daytime brunch/lunch dates either with my family or friends,  but I’ve also worn it for happy hour dates, which tend to be more casual. When I look at this outfit it doesn’t necessarily scream date night, but people are pretty casual around here 99% of the time: think sports jerseys, sneakers, hoodies, etc. So by comparison, this is “dressed up” – but it’s not over the top. And that’s usually my comfort zone – I want to look nice but not totally out of place!

TWO: Leopard Cami + Moto Jacket

 Similar Jacket | Cami | Similar Jeans | Boots (c/o) | Earrings

This is my standard date night uniform of cami + jacket + jeans. In the Spring I wear this combo with my favorite $30 Target Ankle Strap Sandals, but I hate having cold feet, so those are a no-go in the winter! One other thing I love about wearing OTK boots is that I don’t have to worry about the hem of my jeans working with my shoes. Whether it’s pumps, sandals, or ankle boots, I feel like they always make it a little more challenging to get the hem of my jeans hitting just the right spot. It’s so much easier to just tuck them in to these boots and be done with it!

THREE: Shawl Cardigan + Black Cami

Truth be told this is more of a daytime/day date outfit for me. I’m just not very likely to reach for a cardigan for date night. That said, for one thing I see a lot of people wearing this type of top + cardigan combo out to dinner…just not the boots! Ha! So I still think this can work for date night. But second of all, I’d also wear this to a happy hour date, especially if I was already wearing the outfit earlier in the day. I would probably have worn different shoes for daytime, so it’s easy to just change into OTK boots and give the outfit a little dressier and sassier vibe for the evening.

These next three outfits are top view selfies, but I’ll have the front view at the end of this post as well for a better look at the fit on these pieces.

FOUR: Black Blazer + Burgundy V-Neck Top

If you’re not a moto jacket person and still want to dress up your outfit for date night, a blazer is always a good choice! But the boots keep the whole outfit from being too business-y in my opinion. The top I’m wearing here is actually a tunic top. I  shared two more ways to wear it in this post, but it worked out pretty well with a front-tuck here with jeans, adding bonus points to the versatility of this particular top.

FIVE: Green Wrap Sweater + Grey Jeans

This was my exact outfit for my holiday blogger dinner date with Noelle and I loved wearing it! It was dressy enough for the venue but still warm and comfortable. Noelle and I both wanted to choose a little bit of a nicer place since we both have husbands who prefer casual venues. I don’t mind casual, but it’s also nice to have to go somewhere a little fancier now and then, so our girls date was the perfect excuse for that!

SIX: Plaid Moto Jacket + Red Sweater

And last but not least, something with a little bit of a Valentine Red! I usually struggle with styling red, but this plaid jacket has made it easier! This red sweater is pretty thin, so when I layer it under the jacket I don’t feel like it’s bulky or getting bunched up underneath. I usually layer t-shirts or camis under my jackets since I can’t stand that bunched, restrictive feeling! But this isn’t much thicker than a t-shirt so it hasn’t been an issue. 
And finally, here’s one last look at all six of these outfits:
Of course, if you don’t love OTK boots as much as me or they just don’t work for you, knee high boots or ankle boots would work easily work as a substitution in these outfits. But obviously I’m loving the OTK boots trend and trying to make the most of it while it’s still “in!”