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Heading out on a First date? Here’s a Few Plus Size Outfit Ideas

Jeans and a T-shirt for a first date look. You have both of these items ready to go and you can add a few accessories to dress up this look.

It’s 4 p.m on a Thursday.  You are entering your last hour of work for the day and are looking forward to racing home to your TV screen, to finish that final episode of Netflix’ current most binge-worthy. When, low and behold, your crush slides into your DM and has finally worked up the nerve to ask you out on a date. You recognize that your fingers are about 5 steps ahead of your brain because you just agreed to a dinner date at 6. TONIGHT. 1 hour to get home and get ready and no time to run to the store to buy that semi-casual outfit that you could try and pass off as something you just pulled out of your closet. What do you do? Well, first you breathe, because you have all the pieces that you need sitting right in your closet.     

First Date Night Outfit on the Fly 

wine bar

Photo courtesy of Ponce City Market

First things first, you want to be completely comfortable on a first date. The last thing you want is to be adjusting yourself throughout the entire date and lose points for confidence.  What screams comfort more than jeans and a T-shirt? Yes, I said jeans and a T-shirt for a first date look. You have both of these items ready to go and you can add a few accessories to dress up this look.  

The Jeans

First Date Night Outfit jeans

Photo courtesy of NYDJ

You want to show sexy and confident, so a dark blue fitted jean is always a cool clean look.  Make sure it is hugging you in the right places but not so tight that you manifest your 1st date nightmare story when your pants rip. For now avoid ripped jeans, you are never certain where you and your date will end up. That super casual place, may turn into somewhere a little more chic if your date switches up on you or the wait for a table is too long.  You want to make sure you are always ready. The jeans can be worn cuffed or not cuffed but that is depending on what shoes you decide to pair with your outfit. We will talk about this later.

The T-shirt

First Date Night Outfit tee

Photo courtesy of Simply Be

A white T-shirt with a dark blue jean is always a clean look, but I never manage to keep it clean for long. Unless it is a new acquisition, I probably don’t have a white T-shirt sitting in my closet. So find another color, something solid with no writing so that the focus is on your beautiful face.  Black is always a great way to go, it is simple and sharp and it looks good on any skin tone. I mean when Ms. Coco Chanel say’s “Black has it all, It’s beauty is absolute, It’s the perfect harmony” you know that it’s a definite fashion must. Stay away from a tight tee, a V-neck or scoop would work best. Nothing too low cut, we want the focus on that face, remember?  

The Cover

First Date Night Outfit cover

Photo courtesy of Lane Bryant

I am most comfortable with some cover-up. Whether it be a light jacket, a sweater or a duster. It serves as a great piece to dress up a simple T-shirt and jeans.  A Solid Color works best here, too. You can wear black on black but be sure to break it up with a necklace or scarf.

The Accessories

First Date Night Outfit acccessories

Photo Courtesy of Stitch Fix

Simple is the way to go. A modest size pair of hoops, a long necklace or scarf, and you are good to go.  

The Shoes

First Date Night Outfit booties

Photo courtesy of Aerosoles

Flats or booties with this look.  Do not use this time to test out those new pumps that just came in. You want comfort and stability. Put on those shoes that you know you can stay in all day and feel content by the end of the night.  A bootie with a heel is always a cute look and it will also elongate your legs, allowing you to appear more poised and confident.

First Date Night Outfit

Photo courtesy of Stitch Fix

5 minutes to spare. Minimal makeup, enough so you don’t look completely different from your selfies on social media. Not so much that you look like you just came out of a Youtube makeup tutorial.  Grab a clutch and you have just proved to everyone in the world that a woman can achieve a first date look on the fly. Now, if the date goes well and we can move on to how to prepare for the second date. Which we will likely have more time to do.  

What’s your go-to date night outfit? Do you have these items in your closet? We’d love to hear from you in the comments!


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Written By

Hey TCF readers! My name is Shirley I am a curvy girl from Manchester, NH who loves short walks on the beach, good reality TV, and shopping the latest fashion trends that play to my oh so voluptous shape. OK that sounds a little like the start of a dating profile, but i guess that's me in a nutshell. In the day time I am working hard to help shape our future generation, and at night I write. I started blogging because it seemed like I always had something to say about something and I thought what better outlet then a blog to get those crazy thoughts out of my head. I also love the idea of being able to connect with people who look like me and are able to share some of the same things we are facing. “I believe in knowing who you are but without limiting yourself to your own expectation of who you are.” A quote by Charlotte Eliza is a quote that has been instrumental in helping me recognize that this me, is a pretty ok me. Follow me on social media and catch some of my crazy adventures with my family and friends, you will get to see some of the fun outfits I've put together, and just get to see a Curvy girl from lil old NH living life to the fullest.



  1. Jeran

    March 30, 2019 at 7:03 am

    I’ve seen her pull it off! She’s definitely a fashion guru!

  2. Rima Ayoub

    March 30, 2019 at 7:20 am

    Great article Shirley. Thank you for posting this article and giving us curvy woman ideas and examples of what to do on that last minute date. You’re amazing keep writing can’t wait to read your next post.

  3. Fatima

    March 30, 2019 at 8:24 am

    Omg! You get it girl!!!

  4. Shayna

    March 30, 2019 at 9:08 am

    Love it Shirley !! I always love your outfits <3

  5. Rochelle

    March 30, 2019 at 9:33 am

    Hey lady,never case to amaze….fabulous,like you of course😉

  6. Rochelle

    March 30, 2019 at 9:34 am

    Hey lady,never cease to amaze….fabulous,like you of course😉

  7. Bill Fabrey

    March 30, 2019 at 12:40 pm

    Interesting read…so that’s what you ladies do to successfully pull off a first date (or any date) with us gents! Well, there’s a lot at stake for both of us. All great partnerships have to start with that first date.

  8. Julz

    March 30, 2019 at 2:41 pm

    Love this shirley and love you !

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