What to Wear for Date Night

Jess Ann Kirby shares what to wear for date night featuring a Shoshanna blouse

Longer days and warmer nights can only mean one thing, more opportunities for date night. The days (or nights) of couch surfing and Netflix marathons are dwindling replaced with dining al fresco and sunset drinks. I know for me, I want my date night outfit to be comfortable and chic. I like to think of it as dressy-casual. Is that a thing? Newport in general is fairly casual so I’m not going to show up to date night in a bodycon dress and stiletto heels, I guess I wouldn’t wear that anyway but I think you get my point. I thought I’d try something new and break it down to give you an idea of how I come up with an outfit. Let me know if you like this format and I can do it for other outfits too (work style, weekend style etc.).

Jess Kirby wears the Shoshanna Bee Blouse for date night in Newport, RI

A Feminine Blouse

Comfort is really important to me, and you don’t have to sacrifice style for wearability. I love this cold shoulder blouse because it’s feminine with ruffles and a floral print but still comfortable and wearable. While I really like some of the new trendier blouses with the big bell sleeves it’s not very practical for scenarios where you’re trying to eat (picturing myself dragging it through a bowl of salsa). When you’re pulling together a date night outfit make sure you feel good in it and you’re not pulling or fidgeting at your clothes. Something you can just wear and not think about it is important.

Cropped Jeans

Probably no secret that denim is my favorite for pretty much anything and everything. There’s just so many ways to wear jeans and I feel most comfortable in them. A few things to think about when picking out a pair of jeans for date night; make sure they aren’t too tight. There’s nothing worse than having to unbutton your pants because you can’t breathe after dinner (been there done that). A little stretch goes a long way. I really love slightly cropped or cropped flare jeans right now because they elongate the legs and show off your shoes. It’s all about proportion too. If you’re wearing skinny jeans balance it with a slightly looser, flowy top. On the other hand if you’re wearing a wide leg or flare, keep your top half tailored.

Raw hem jeans, lace up sandals and a floral blouse is a great date night outfit
Jess Kirby styles a date night outfit in raw hem jeans, floral blouse and lace up sandals


The shoes you pick for date night are crucial. There’s nothing worse than wearing heels you can barely walk in and I see it all them. Someone teetering down the street looking as if the slightest breeze might topple them over at any second. There’s a time and a place for high heels but if you can’t walk in them, don’t wear them. My favorite is something with a 1-3″ block heel. I love lace-up heels right now and this pair is a soft suede with a heel that’s just high enough to give me a few extra inches without feeling like I’m going to break my ankle walking around in them.


Full disclosure, I know I have said many times that I just don’t understand spending thousands of dollars on handbags and shoes. I still feel that way but I did recently splurge on a Chloe Faye Leather Bag. I’ve wanted it for years and it felt like a timeless style I’d wear again and again. I’m here to tell you that I wear it ALL the time. Which leads me to my point that it’s ok to splurge on accessories that you’ll get a lot of use from. Your accessories can make or break your look. With this date night outfit, because I’m wearing a top that has a lot going on, I kept my accessories simple with some delicate rings and my Chloe bag.

Date night style on Jess Kirby wearing raw hem cropped flare jeans and a floral cold shoulder blouse
Date night outfit inspiration by Jess Kirby wearing the Shoshanna Bee blouse

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  1. I loved this post!! Such a cute outfit, and I’m with you comfortable is the key to make a great night last! 🙂


    6.15.17 | Reply
    • Jessica wrote:

      Thanks Jenna, couldn’t agree more!

      6.15.17 | Reply
  2. Natali wrote:

    Fantastic blouse, you’re looking beautiful in this effortless and girly casual combo!


    6.15.17 | Reply
    • Jessica wrote:

      Thank you so much Natali xx

      6.15.17 | Reply
  3. Rach wrote:

    These are great date night ideas! That top is so cute, feminine, and flirty!


    6.15.17 | Reply
  4. Jill wrote:

    Simply beautiful look!


    6.17.17 | Reply

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