A Dress A Day: Date Night (Day 1)

What to wear for date night in summer

Red Midi Dress (also found one in navy!) | Rockstud Heels (designer dupes here) | Black Tassel Bag (also found here) | Black Sunglasses | Pinata EarringsLipstick in ‘Bawse’

I am so excited to kick off a new series today! This series is all about my favorite thing: dresses. I originally wanted to post a dress a day for the entire month of May. However, Chicago’s weather had other plans. So, I’m starting today which is exactly halfway through the month!

Initially, I was really torn about not being able to start it on May 1. I had set a goal, did everything in my power to plan and prepare for it, and then Chicago suddenly became Seattle. Rain galore. But then I realized that this is my blog and for lack of a more original phrase, I’m the boss. Unlike in my day job, I get to make the decisions (except Mother Nature and I seem to be dueling for the CEO position right now). All that to say, I’m starting today because I feel like it. I’m going to try to do the full 30 days so make sure to check back daily. You can access all of these posts here or just look for anything titled “A Dress a Day”.

It’s my goal to deliver 30 amazing dresses to you. From what to wear for casual errands, to what to wear as a bride this summer, it’s coming! And who knows, maybe I’ll keep this going even longer. If you have a certain type of event that you need a dress for, let me know and I’ll add it to the list!

But let’s start with this red midi dress AKA the perfect date night dress. There is nothing that makes a man turn his head more than a lady in red. This dress is just proof that you don’t need a low cut top or a short skirt to get stopped in the streets. Matt and I were headed to dinner after this shoot and I had people of all ages and genders asking where this dress was from! The twirl worthy skirt is unbeatable. The fabric just flows. I even caught myself flinging my skirt around as we were walking back home later.

This dress is great for a wedding, date night, and could even be paired with a blazer for work. It’s just that versatile. I love pieces like that because I don’t have to let something sit in my closet, feeling guilty not wearing it. Anyone else do that? If you’re not feeling this one, I’ve linked to some of my favorite alternatives below! For the most part, they are really forgiving in terms of flattering all body types (especially the fit and flares).

I’m also excited to host a link up today with Walking in Memphis in High Heels and The Fashion Canvas! Make sure to check out both of their blogs for more great style inspiration. See below for the link up – share your look with us!

Today’s theme is accessories and today I’m wearing one of my favorites: these Valentino heels. They are my favorite investment piece (the kind of piece that will last you 10x as long as the $100 alternative). These heels are so incredibly comfortable (the block heel version isn’t as comfy IMO which is surprising). I’ve literally worn them everywhere. You’ve probably seen these on the blog maybe 20 times in the last year? I wear them to almost every wedding, tons of date nights, and even my sister’s bachelorette party. They pair perfect with your favorite jeans too for a more casual vibe.

If you’re not ready to splurge, I found these Valentino dupes last week! Amazon has really been stepping up their fashion game lately and I showed how many of my outfits have come from there here! Often times, the prices are a little lower too.

Do you have a dress that you always wear on date night? What is your night out style?

trend spin linkup with accessories

Rebecca Minkoff tassel crossbody bag

Betsey Johnson red crepe midi dress

A red midi dress with tie shoulder straps

windblow red skirt with valentino rockstud heels

A flattering red dress for work with a long, flowy skirt.

Black Karen Walker sunglasses Number One

A stunning dress to kick off the a dress a day series!

twirling in a sexy black and red combination for a night out on the town


36 thoughts on “A Dress A Day: Date Night (Day 1)

  1. I’m loving this blog series idea! I can’t wait to see all your gorgeous dresses! I’ve got to say, this color might be my absolute favorite on you. It’s so cheery! The darker accessories really make it pop, and you’re right – it’s perfect for date night!

    Stephanie // SheSawStyle.com

  2. You look so stunning in this color! I love the classic silhouette of the dress too – so chic!

  3. Red is gorgeous on you Jenna. Such a pretty dress. It would be perfect for the upcoming wedding season. Love the bag, too. Nice to see you co-hosting with Laura, today. =)

    Hope you enjoyed Mother’s day weekend! I welcome you to stop by my blog and join my Thursday Moda linkup on Thursdays. It goes live every Wednesday night (tomorrow) at 6.00 PM EST. Thank you. =)

    Ada. =)

  4. This dress is so beautiful! I was actually thinking, as soon as I saw it, that you’re never too old to want a dress you can twirl in! This one is gorgeous!

    Virginia
    More to Mrs. E

Let me know what you think!