A Sexy, Simple Lifehack: Style Your Pajamas for Date Night


What is it about the right pair of pajamas that can make you feel comfortable and sexy at the same time? I’ve mentioned a few times before that I want to simplify my date night looks. I’m willing to admit that I’ve held up our date night plans a time or two because I’m changing my outfit *one more time.* I’m all about being stylish and comfortable, but come on, ain’t nobody got time to miss out on that pre-dinner happy hour! I’m trying to maximize every last second of our date nights, but without compromising my style. It’s with that in mind that I present to you…

Date Night Pajamas

If you follow me on Instagram, you know I love wearing pajama-inspired looks out. I feel like the lovechild of Blanche Deveraux and Rhianna when I’m sporting my PJs on the town. And, I’m talking legit on the town, not just the grocery store or bus stop. I’ve generally styled them more casually with my fave pair of Levi’s, but one of Gwen’s recent IG posts styling a gorgeous pajama top with a denim skirt got me thinking I could step up my jammies style game. This time, staying in our fave, luxurious staycation hotel got me thinking I could turn up the sexy on this adorable J. Crew shorts pajama set. You’ll have to scroll through our date night routine (which also involves scrolling) to see the magic I created.

Yep, I traded my Levi’s for a leather skirt, and I’m all, “Damn, Gina!” Funny, I was looking at one of my very stylish friend’s IG feed recently (Hey, Jenny, HAAAYY) and she styled a leather skirt so flawlessly, I was moved to confess in her comments that I didn’t have one. She shamed me, and I deserved it. You better believe I’ve got my life together and am strutting off into the sunset in this sassy little number. I’ve been thinking of all the ways to style it, but the play on hard and soft by pairing with these jammies is already a fave. I initially envisioned styling with a satin PJ, which I still think would be very chic. I just couldn’t pass on the pink with black piping combo! The embroidery on the pocket is so cute and screams “sleepwear,” which may be just a little cooler than wearing something that only looks like jammies, ya know? Either way you slice it, don’t sleep on this trend. I think it’s gonna be here a while.

Outfit Details

Short Pajama Set (J. Crew): So cute, right? They’re TTS, I’m wearing size M (size 10, for reference).
Faux Leather Skirt (H&M): I liked that the material is thicker than most leather I have. It’s very comfortable, and I was happy it didn’t ride up when I walked. It’s TTS, I’m wearing size 10.
Barely There Sandals: These were such a great buy, as I’ve lived in them all summer. They’re TTS. I’ll be sad to pack them away for the fall…or maybe it’s time to try socks and heels again…
Crossbody Bag (similar, Madewell): This is my go-to date-night bag. It fits my phone, card holder, and 18 tubes of lipgloss. You know, the essentials.
Watch (Movado): Classic with a two-tone metal twist. This watch was a Christmas gift from my husband years ago and I still adore it.

Kate Spade Cat Eye Sunglasses (similar): These are a few years old, but I’m pretty sure they’re the Jazzlyn style. It looks like Amazon is the only retailer that has black in stock, but the Genice and Nastasi are pretty close, too.

Cuff and Necklace (Etsy): My everyday jewelry edit is 90% from Etsy. I love everything I’ve found there, but it’s nice that one of the stores, Red Giraffe Designs is local and woman-owned.

Trent’s Outfits (similar): Pajama pants/t-shirt; Date-night shirt, jeans, and sneakers. 

Shop the Pajama Look

But alas, whether you slip into these perfect pink PJs or something else, you’ll be thanking me when you roll right out of bed to hit the town like the foxy mama you are. And hey, maybe you can roll right back into bed with said jammies later…your call. You know the deal, I wanna see what you end up working out, so follow/tag ya girl on Instagram and follow along on Liketoknow.it to instantly shop this look!


Photos by Sweet Leaf Photography