I’m trying to keep the outfits and styling tips coming for y’all since I know you find them helpful, so today I thought I’d give some tips on how to style a winter date night look! I’m not gonna lie, it can be HARD for me to feel motivated to get out of leggings and oversized sweaters (they’re just so dang cozy) this time of year. Anyone else? That being said, I like to keep things simple and comfortable – even when going out with the boy.

A lot of your outfit depends on where you’re going for your date, obvi. If you’re keeping things pretty casual and just headed out to dinner or maybe to a movie, this formula for styling your date night look will work like a charm! It’s quick and easy, which I’ve found to also be important because when I start to overthink things, well, y’all know how that usually goes. So, next time you’re getting dressed for a date night this winter, remember these three tips!

Distressed denim

Will there ever be a time when distressed denim isn’t cool? It just seems to work for almost every casual event (as long as the jeans aren’t TOO distressed). For my date night look, I went with this black pair (fit TTS) because I think black dresses things up a bit more. It makes me feel a little more polished and pulled together.

Personally, I’ve had a hard time finding the *right* wash of black distressed denim that’s dark but still looks like denim if that makes sense? And then I have a few other requirements for my jeans as well: I prefer high-waisted, stretchy so I can move, and I like to buy cropped jeans since I’m a bit shorter (because who wants the extra step of going to the seamstress?!). Oh and also, they must have a relatively skinny (9 inches or less) ankle opening! Because I don’t know about you but pairing jeans with booties these days (WITHOUT cuffing my ankles) is no easy formula to get right! Can I get an amen?! ALL THAT BEING SAID, I found a pair that I LOVE and so I bought them in three colors. And this is the black pair! They’re pretty pricey but WELL worth it in my opinion!

Dress in layers

Dressing in layers for date night in the winter is critical, we know this. First, you never know if the restaurant, theater or wherever you go, will be cold. And being constantly cold (or hot) is the WORST. Start your layers with something light – not a tank because it is winter after all, but something you can put a sweater over.

I went with this lightweight turtleneck that I’m absolutely loving and added this very cozy, shorter cardigan ($55) on top. Why the shorter length? It makes the outfit feel a little more worthy or a “date night” look, plus these bomber/cropped style are better on petite frames (aka short ppl like me!).

Heeled booties

Y’all have probably picked up on the fact that I love a good bootie! I wear them almost constantly during the winter (and Fall!), so it’s no surprise they’re a key factor in my winter date night formula. I like to go for one with a heel because it makes me feel dressy without being dressy. Does that make sense? And if you live in a place where it snows and closed toes are a must, I highly recommend a good pair whether it’s date night or not. These are the booties I talked about (and wore!) in this blog post round up of heeled booties a few weeks ago.

I hope y’all found this helpful! And if you put together a date night look using these tips, make sure to DM me a pic! You might just see it on stories :)

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