When I’m in the winter blahs – or any time my routine feels too ‘routine’ – I have something that totally picks me up. I schedule things to do. Like lunch with friends. Or an afternoon of window shopping. Or a family movie night. Or a nice date night.
Date nights are an occasion that I often work on with clients. And I think it’s because it’s something out of the norm. They want to get dressed up – but they don’t want to get dressed up too much. They want to feel comfortable – but also a little special. And they don’t want to buy a whole bunch of new things – they want to work with what’s already in their closet.
It often feels like warm weather date nights are easy to dress for. You grab a cute dress and sandals and you’re kind of good to go. But cold weather date nights, that’s another issue. How can you look cute? And special? And elevated from your everyday? When it’s still freezing outside?
Well, I’ve got you covered. Here are 6 date night outfits that are perfect for cold weather. Along with a few tips to enjoy your date night style all through the winter.
MIDI DRESS & HEELED BOOTS
The same dress you wore to an afternoon wedding in the spring becomes winter-worthy with heeled boots and a wool coat. Just add tights and you’re good to go. And if it’s really cold, trade your tights for leggings and add a thin turtleneck underneath. Read this for other layering tips to take you from now and right into spring.
COLD WEATHER STYLE TIP: Dark based prints feel more cold-weather appropriate (but they’re totally okay in warm weather, too). So, remember this when you’re picking out a dress that you want to wear year-round. And a bold color coat is the best way to stand out from the crowd of black outwear.
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DRESSY TOP & FAUX LEATHER PANTS
You know those fun and festive tops you wore all December? You can still wear them throughout the rest of winter. Velvet, sequins, lace and satin are great ways to feel special now and for the next couple of months. Pair them with faux leather pants (an ideal way to stay warm) and you have an outfit that’s perfect for date night. Here are 5 more ways to wear your faux leather pants.
COLD WEATHER STYLE TIP: When you’re bundled up all day long, you can transition to evening by showing a little skin. An open neckline is probably the easiest way (since you don’t want bare arms or legs). But you can also try sheer-ish tops like this one – just layer a tank underneath for coverage.
SWEATER SET & CHUNKY BOOTS
Nothing is cozier than a sweater, right? So, how about a matching sweater and skirt to set the mood? When you’re always in pants or leggings, a skirt just feels different enough to shift your mindset from days focused on work to an evening focused on you and your partner.
COLD WEATHER STYLE TIP: When it’s really cold, it’s not just about the layers you see – it’s also about the layers you don’t. So, go ahead and add tights or leggings under skirts and dresses (or even jeans). And wear a long sleeve t-shirt under your sweaters. Layers trap warmth between them, so two thinner layers are often warmer than one chunky one.
STATEMENT JACKET & JEANS
Don’t save your dressy jacket for parties – date night is a good enough reason to pull it out. And this goes for your velvet jacket or sequined bomber or satin blazer (like this one). Pair it with jeans to take it down a notch. And layer a thin sweater underneath when a blouse just won’t cut it.
COLD WEATHER STYLE TIP: Don’t underestimate the power of accessories to shift the tone of your look. An outfit can be totally transformed with a change of accessories. Fun jewelry and metallic shoes are one of the easiest ways to do it (especially when it’s cold). Click here to see why I love metallic accessories year round.
SWEATER & DRESSY SKIRT
As with the other outfits, it’s not about wearing dressy pieces head to toe. It’s about using one dressy item to make the occasion feel special. So, grab your favorite dressy skirt, add a chunky sweater or cardigan and get ready to enjoy a little time without the kids (heels optional).
COLD WEATHER STYLE TIP: While I’m on the topic of heels, shifting from flats to heels is another simple way to signal date night. And the best part – you can always wear tights and socks with your boots and booties to stay warm.
COZY SWEATER & CORDS
When most of your days are spent in fleece leggings or jeans, getting out of them is the quickest way to prepare for casual date night. Because not all date nights are dressy occasions – sometimes a pizza date is exactly what’s needed. So, grab a pair of cords and a fun sweater and you’re basically good to go (just add outerwear). And if you’re tired of wearing snow boots every day, how about chunky loafers with socks?
COLD WEATHER STYLE TIP: It’s easy to get into a funk when the holidays are over. But color is a great mood elevator. So, wear shades that flatter your face for never-ending Zoom calls and pick pop color accessories just for fun. If you’ve never played with pop colors, here’s how to do it.
Are you ready for your cold weather date nights? If you have any questions about what to wear (or how to wear it), drop a comment below. And if it’s not cold where you are, check this out for a bunch of warm weather date night looks.
If we’re not already friends on social media, let’s fix that! You can find me here on Instagram and here on Facebook. And if you use Pinterest, I’m pretty active on there, too.
Outfit details (from top to bottom):
Farm Rio dress, Ted Baker wool coat, Marc Fisher suede boots, All Saints earrings
Alice + Olivia top, Paige faux leather pants, Herno faux fur jacket, Marc Fisher booties, Saint Moran necklace
Naked Cashmere sweater & skirt, Zara vest, Ecco boots, All Saints scarf
Frame satin blazer & jeans, Halogen sweater, March Fisher booties, Stella + Ruby necklace
Favorite Daughter cardigan, Karen Kane slip skirt, Barbour coat, Ted Baker booties, Saint Moran earrings
Me + Em sweater, Wit & Wisdom corduroy pants, Blondo loafers, Rebecca Minkoff beanie, And Other Stories socks
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Paul Julch helps busy people to streamline, organize, and update their wardrobes so they can get dressed with ease and always look stylish and feel confident. Any budget, any lifestyle, any body. His business is Urbanite|Suburbanite, and he works with clients to develop a modern, current, versatile wardrobe that expresses personal style rather than trends. Paul is based in the SF Bay Area, and remote wardrobe & style coaching is available for out-of-towners. Visit Paul’s website for more style advice styling tips and tricks.
