Turn Heads This Fall & Winter with These 3 Chic, Comfortable & Warm Date Night Outfit Ideas

Let’s talk date night! Anyone else think date night outfits can be some of the trickiest to put together, especially as we get older? You want to be comfortable and confident, but you also want to look sexy. But not the kind of sexy where you look like you’re trying too hard or letting it all hang out. It’s a whole balancing act! Can you look sexy and sophisticated while also being warm and cozy? You bet you can.

Today I’m sharing 3 date night outfit formulas that give you distinctly different looks for fall/winter. But here’s the really great news…each look includes versatile, comfortable basics you can wear again and again. AND these are simple outfit formulas you can rely on for any date night (or girls’ night out!).

Huge thank you to Saks Fifth Avenue for sponsoring this post. All thoughts and opinions are my own.

On the hunt for chic fall outfit ideas? Make sure you check out our new fall lookbook!

GET THE LOOKBOOK

Graphic Tee & Blazer

On my top half, I’m wearing a Cinq a Sept, Je T’aime graphic t-shirt (means ‘I love you’ in French). I just love this sweet message for date night, but you could always substitute a solid crewneck tee or tank if you prefer. Over the tee, I have on a classic black longline scuba blazer by Veronica Beard. This blazer is a go-to that I reach for all.the.time. The fabric is luxe but not crazy heavy so you can easily layer underneath it and even over it. Sticking with the love theme here, I added 2 layered, 18K gold vermeil necklaces by Jennifer Zeuner…one with a heart pendant and one slim choker. You’ll be seeing more of these necklaces throughout this post.

Jeans & Booties

On my bottom half, I’m wearing a pair of dark-wash cropped jeans by Mother and some fun and funky, Stella McCartney platform sock booties. The jeans are a great length for me at 5’4″ and the sock booties work beautifully underneath them. But let’s take a minute for these booties! They really turn up the volume on this outfit and add some extra edginess to the whole look. They have a 4.5” inch heel, but a 2” platform which is pretty manageable to walk in. These would be great for a date night when you’ll be doing a ton of walking or you’ll be outdoors and stiletto heels are out of the question…but you still want to look modern, cool and sexy. These are a splurge, but worth it in my opinion because I know I’ll wear them a ton with pants, jeans, and dresses. I’ll link a more budget-friendly option below too.

Style Tip: Don’t let hair and makeup be an afterthought! I kept my hair down with some edgy bangs to enhance the outfit and look.

Black Wrap Top

I love the waist-cinching detail on this Rag & Bone Ponte knit wrap top and it also has good coverage. It’s thick enough that you could get away with wearing it without a bra (depending on your bust size and comfort level). I really appreciate the flattering neckline to highlight the layered necklaces and the asymmetrical hem that makes it a bit more special. It can be tough to find a pretty date night top with long sleeves that will keep you warm and comfy but still look chic. This is one of those unicorn tops!

Dark Wash Jeans & Platforms

Where are my tall ladies? These high-rise dark wash jeans by Cinq a Sept are super long and leg-lengthening with a 34.5” inseam. When I tell you they’re long, I’m wearing a pair of 6” Schutz platform heels and they are the perfect length (I’m 5’4″ for reference). If you want to look taller and leaner, a dark wash pair of jeans and platforms is the secret sauce. The platform itself is about 2.5”, with about a 6” heel which is going to be way more manageable to walk in than say a 6” stiletto. (Do they even make those?) Of course, you could also wear your dark-wash jeans with regular heels or heeled booties if you prefer smaller or chunkier heels.

Style Tip: Let’s say you want to turn up the volume on this look and wear it to a holiday party. Just swap out the layered necklaces for something with a little sparkle, add a red lip and/or nails and an elevated clutch.

Velvet Blazer

How gorgeous is this structured velvet Zhivago blazer? The strong shoulders help create the illusion of a smaller waist, and the gold buttons are such a luxe detail. This blazer would also work beautifully for your holiday events or parties. It’s a great “wear-now-wear-later” piece that will keep you warm, but not too hot.

Faux Leather Bustier

Under the blazer, I’m wearing a sexy, cropped, faux leather bustier top by Milly. I love everything about this top from the sweetheart neckline to the one shoulder strap and twisted bodice. It’s so chic…and definitely Wowza for date night, but still very tasteful. You could wear the blazer open to show a bit more of the top and a little more va-va-voom. I’m still wearing the same layered necklaces, but this time I moved the heart pendant to the back. Always remember you can wear your necklaces backwards too.

Slimming Black Trousers

For this outfit formula, I swapped out jeans for a pair of sleek and uber-slimming Veronica Beard black trousers. These are comfortable and lightweight which helps offset the heaviness of the velvet blazer. They have a high-rise, slightly flared leg and a 33” inseam which is elongating and slimming. The pants also have a leg-lengthening center seam down the front. On my feet, I’m wearing Veronica Beard suede booties. The booties have been a heavy hitter for me for multiple seasons now. They are super versatile and comfortable.

Style Tip: Trousers are super on-trend right now and you can wear them for dressy looks or super casually with a pair of sneakers.

Bonus Top

I just had to include one more top that was too good not to share for your date night looks. This elevated satin top by Milly can be styled SO many ways. The crystal embellishment at the neckline gives it more of a dressy or even holiday vibe, but you can wear this with your dark wash jeans, trousers, skirts, leather pants…it’s just that versatile. I paired it here with the same trousers and booties from the previous look but it would look amazing with your dark wash jeans too. And of course, thinking ahead to the holidays, this top would be SO perfect!

What’s your favorite thing to do on date night? Live music, special dinner, a whirlwind trip to Paris? Please share in the comments below!