What to Wear (or not wear) for winter date night

Beverly Hills, CA

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Getting dressed for date night can be tough on a good day. Add in cold winter weather, wind, rain, and potentially even snow (who is crazy enough to go out in the snow?) and that struggle gets multiplied. On the one hand, you want to look your best, but on the other, you don’t want to spend your night pretending you’re not shivering. 

I used to be the queen of underdressing when I first moved to L.A. because every temperature seemed warm compared to my New Hampshire home. However, I’ve learned that I run cold and I’m usually chilly despite the lack of frost. And now, I am sure that I dress for comfort. That’s really the biggest thing. You have to feel comfortable! 

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Some of my don’ts:

Don’t go for something that’s too revealing. Of course, this can mean different things for different people but in my experience feeling overexposed is never a good thing. What’s sexier than showing a ton of skin? Being able to enjoy yourself and being dressed for the weather outside. It’s that simple. 

On the other end of the spectrum. Don’t wear clothes that are overly baggy or puffy. You want to be comfy but you don’t want to look like you’re dressed for a day of sledding ;) 

Don’t take a fashion risk that you’ve never tried before! I’ve done this a few times but especially on a first date, it’s not the best idea to try on bold trends that you’re not even convinced you love yourself (cue that neon leotard you’re trying to bring back). Again, if you’re not thrilled with what you’re wearing, it’s likely that it’ll spill over to how you feel on the date.

Some of my do’s:

Add accessories! Great rings and jewelry go a long way. I am a huge fan of gold layering necklaces and rings. They always look good and can elevate your go-to skinnies and tee, making you look and oh so put-together. If you’re braving the elements, throw on an oversized scarf with an edgier leather jacket. 

Go for effortless combos. A cropped sweater with high-waisted jeans/maxi skirt or a mini dress and over-the-knee boots (like I’m wearing here) are always great options. You can throw on tights with the dress (depending on the temps where you live) and add a long trench for a look that’s both flattering and warm!

Layer up! Opt for form-fitting bodysuits (always flattering!) and pair with a blazer or statement coat. That way you can take add and remove layers to suit your environment!  

These are things that have worked for me and my personal style but ultimately, it’s up to you!

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COMFY-CHIC

Santa Monica, CA

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Yes, you can make a statement in comfier clothes. From oversized dresses to baggy sweaters, even the coziest pieces can pass for chic with the right accessories. When I tried on this loose-fitting Topshop dress, I knew it was too good to pass up. Flowy yet flattering with a belted waist, it pairs well with OTK boots for a low-key winter look. So if you're on the hunt for an outfit you'd basically love to live in, this number is a good start. 

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Dress: Nordstrom/Topshop

Boots: c/o Goodnight Macaroon

Multi-Color Ring: c/o Baublebar

Bag: Nordstrom

Hoops: c/o Sugarfix by Baublebar

Necklace: c/o J.Bubs Jewelry (Take 30% off with code: kelly30)

Bracelet: c/o Grand Avenue Jewelry

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