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4 Winter Date Night Outfit Ideas to Copy

4 Winter Date Night Outfit Ideas
4 Winter Date Night Outfit Ideas to Copy

Sooo…what do we wear “out” these days?

One thing I feel like we (“we” as in, thirty-something year-old women) were not warned about our thirties: It’s like, really hard to find outfits that are “sexy” while feeling age appropriate?! We no longer pull on tiny spandex dresses (with no coats–why did we never wear coats?) to go out like we did in our twenties–but we certainly still want to look and feel great (but comfortable, and seasonably appropriate) when we go out on the town (prior to being home and in bed by 11pm. Being in your thirties is the best!)

This is one of my most requested blog post topics, and I think I should probably turn it into a series, because it seems like we are ALWAYS needing some idea inspiration in this department, right!?

So let’s talk about date night outfits today! In particular, four examples of outfits you can wear out right now, in winter. (Yes, even if you live in Chicago!) Whether you’re planning a night with the girls or have a hot date–I hope today’s post gives you a few helpful tips!

4 Winter Date Night Outfit Ideas to Copy

4 Winter Date Night Outfit Ideas

Top: Reformation (TTS, also comes in black! Wearing small) // Jeans: Levi’s Wedgie Straights (I cut the hem off of mine to make a raw hem–they’re also available on Revolve and very similar style of Levi’s on Amazon)// Boots: c/o ABLE (TTS–use code JESSKEYS15 for 15% off! Many sizes are out of stock, but if you sign up you can get notified when they come restock!) Dolce Vita also makes a similar style with a lower heel, and they’re on sale!  Belt: Sezane Jones Belt (TTS, but be sure to measure!) Earrings: sold out but identical on Amazon (the 30mm are closest to the size I’m wearing!)

Winter Date Night Look #1:

First up, one of my favorite tops to wear “out”—I actually bought it years ago and just realized they still made it and I’m so happy! I love it because it’s long sleeved, the material is super soft and comfy but it’s still “sexy” while still being casual (so you can wear it to a dive bar with sneakers or dress it up with heeled booties and it’s appropriate both ways!) It also comes in black! (Here’s the bra I wear with it—I unhook the center hook so you can’t see it!) 

Here I styled it with high rise straight leg black jeans and heeled booties to dress it up a bit (I think black jeans are a bit dressier than blue jeans!) If I’m wearing something tight or that shows some skin up top, I like to balance it out with something not so tight on the bottom. This way it looks sexy yet tasteful as opposed to sexy and hoochie/trying too hard. Does this mean you can’ wear skinny jeans? You absolutely still can! If you love skinny jeans, rock them! (I still do!) If it’s feeling too “tight on tight” for you, add a jacket (or blazer, or chunky cardigan) over the top to balance things out! 

Optional: this look also looks great with a leather jacket! (This one is ABLE’s Maha jacket, which I highly recommend–currently is out of stock but they’ll be doing a restock soon!) Totally could’ve gone with either black, brown, or tan here if you have any of those currently in your wardrobe.

What about cold ankles? 

Anytime I post an outfit with bare ankles in the winter, I get this question! I’m not often walking anywhere for a night out in the winter. It’s just too cold and I don’t want to deal. I’m either driving, or taking an Uber–so I’m more than happy to have bare ankles for the 4 seconds I’m outside to and from the car.

However, if you DO want to avoid exposed ankles, here are my suggestions.

First, these pants are too cropped to wear with socks in my personal opinion. If I wanted to wear socks, I would wear black socks and put on longer black jeans so there’s just a TINY sliver of ankle showing! OR I would wear skinny jeans that are very tight at the ankle (and therefore no bare skin is showing!) You can apply the same methodology to the bottom outfit, too!

4 Winter Date Night Outfit Ideas

date night outfits in your 30s

Top: Abercrombie (took my regular size, small, but bustier gals may want to size up!) // Jeans: Levi’s Wedgie Straights (also available on Revolve and very similar style of Levi’s on AmazonBelt: Sezane  (TTS, but be sure to measure!) Earrings: sold out but identical on Amazon (the 30mm are closest to the size I’m wearing!) Boots: old but Blondo makes a super similar pair (that are waterproof!)

Winter date night look #2:

You saw this Abercrombie top in last week’s try-on and it’s the perfect going out top in my book (you know, for my 33 year old self). Like the above top, it’s a little sexy–shows just the right amount of skin and hugs the right places–without being over the top (and it doesn’t feel like a “sexy 22 year old top”) Again, because it’s tight on the top, I like pairing it with straight leg jeans on the bottom to balance things out. 

I think the accessories here really take this outfit from good to great–the belt adds a little extra something, and the pattern/edginess of the boots makes it a lot more interesting! While this would’ve looked cute with black booties, I went with snakeskin to give the outfit a little more edge!

30s date night outfits Lace camisole outfit ideas

Boyfriend blazer: Old Everlane (love their blazers) this one is a similar look // Faux leather pants: Commando (size up, I went with a medium!)  Lace camisole: Sezane (TTS) Earrings: sold out but identical on Amazon (the 30mm are closest to the size I’m wearing!) Cap-toe midi heels: old but Tuckernuck has some identical ones! This pair is also very similar!

Winter Date Night Look #3:

I’m always asked for more ways to style a blazer, and this is one of my favorite ways: dressed up for a night out with a slinky lace camisole underneath!

What makes this combo work so well? The juxtaposition rule! Something masculine + something feminine is always a winning combo. Additionally, the oversized blazer balances out the sexy elements of the camisole. Here I styled it with new-to-my commando  faux leather cropped flares! I love that they’re a fun mix-up from leather leggings or jeans (they fit the same as their leggings do!) I think paired with something looser on top, they’d totally work for a more casual/fashion-forward office, too!

Why do they work well here? Because they also bring a contrasting element to the lace camisole (the edgy faux leather balances out the sweetness of the lace–and the tightness of the pants balances out the loose fit of the blazer!)

And for the shoes:

Some chic cap-toes add some polish to bring the whole look together! I bought these shoes many years ago and I can’t tell you how much wear I’ve gotten out of them. While this exact pair is sold out, there are plenty of similar versions out there–this pair is identical with great reviews. I think it’s a combo of the style (the cap-toes are so elegant and chic) and the heel height (makes you feel dressier than flats but easy to wear all day/walk in unlike taller heels!) I wear them year-round and they’re a fantastic staple to add to your wardrobe. 

4 Winter Date Night Outfit Ideas to Copy all-black Winter Date Night Outfit

winter date outfit inspiration

Bodysuit: old but very similar here from Madewell and Amazon (also love this square neck version) If you don’t love bodysuits, you can get the same look with a tight-fitting turtleneck! // Jeans: Old Navy Fleece-lined “warm” jeansmore colors/washes here! (run a little roomy, order your regular size if you like a bit of room, you can size down if you want them tight!) // Boots: Blondo (also on sale on Amazon in some sizes) run TTS!  // Belt: Sezane  (TTS, but be sure to measure!) // Earrings: sold out but identical on Amazon (the 30mm are closest to the size I’m wearing!) Leather jacket: c/o ABLE–coming back in stock soon! (You can use code JESSKEYS15 for 15% off other ABLE items in the meantime, though!) ) Camel coat: very old from Everlane (they still have a couple in stock!) but I always recommend J.Crew’s cocoon coat (reviewed here)!

Winter Date Night Look #4:

Last but not least, you can never go wrong with all black. I think it’s a foolproof way to look chic, casual, and in this instance–WARM–at the same rime. Plus, with an outfit like this, you’ll never be too underdressed or overdressed. It’s casual enough for a bar but nice enough for a nice restaurant! 

This is what I will pull on anytime I’m going out and it’s freezing outside. A turtleneck bodysuit (or a tighter thin turtleneck that gives the illusion of a bodysuit!) is a fantastic winter staple as you can wear it anywhere all by itself or as a base layer. I often pair my bodysuit with my favorite fleece-lined skinny jeans (SO WARM), which are perfect for tucking into tall boots! You’ve got yourself an air-tight outfit right here.

Because black on black (especially with a turtleneck) can sometimes feel a bit mime-like on its own, the accessories are what make the outfit! I love a statement belt, (I LOVE Sezane’s belts!) statement earrings, or if I’m going more casual, a neck scarf to break things up and make it chic and intentional rather than costume-like.

Layering tip: If I’m not walking very far or if I’m taking an Uber or driving somewhere, I like to wear a coat that’s cuter/nicer than my puffer—often I will layer a leather jacket underneath if I want extra warmth. (I like doing this for all coats if I want just a bit more heat!) It looks cute AND its practical! 

Hope this was helpful in curating your next winter date night outfit! ♥️