What to Wear on a First Date - Plus Size Clothing Tips

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I'm going to be short and sweet: (Probably) do as I say, not as I do. I met my love at a backyard barbeque wearing worn jeans, a black hoodie,  old converse shoes and a scowl on my face. He was still interested for some reason, but I sure stepped it up once we went out on first official date. And, even though I was thinner, I was still a size 12, still self-conscious about what would look good on me and still plus sized. I've also made a ton of date night fashion mistakes and like to think I have learned from them and can share this information to help other woman dazzle on dates.

So, here is my two cents about plus-size clothes for date night.

1. A Smile. Save the eye roll. You know how annoying too-cool teenagers are? Don't follow the same pattern; smile and the world smiles with you. (Unless you're in France, but that's a different story!) Be pleasant, be genuine and if it's a great date, you'll feel the vibe between you two. Even if it's not a great date, and you know you're not interested, smile and keep your grace-- you don't have to play the attitude card just because sparks don't fly. It'll help move you forward to the next date, which will hopefully be with Prince Charming.



2. Minimal Hair & Make Up. I like to describe this as the "Christina" complex-- many woman opt more towards the overdone nature of Christina Aguilera on a date instead of the usually preferred, more natural Christina Hendricks look. More makeup does not mean better.

I'm going to say this knowing I might run the risk of sounding ignorant because I KNOW I have done this in the past: Do not spend hours doing your hair and makeup because you want to create an infallible armor to mask insecurities you have about being "plus sized." Or, insecure because you just had a bad breakup, or because you're on your period... The point is, don't hide behind overdone hair and pancake makeup! Turns out, this kinda scares a lot of great guys off.

Don't do it!

I know trying to look "natural" can actually involve a lot of hair mousse and a roller brush and an arsenal of earth-toned makeup, but that should really be your aim for this first date. Leave the vibrant green eyeliner and coral lipstick at home. Be you. You are pretty, not your makeup. Make it look natural and flowing--not that you're fighting a war against rogue drag queens and the band Kiss.

If it's your style, wear bold colors in your outfit and not on your face for this one--let the guy see you and make a connection based on your personality, not the fact that you love wearing feathered fake eyelashes. It can be distracting.


Beautiful and minimal


3. Keep the Girls In. Hey, they are my best asset, too. That doesn't mean they need to come out to play one Date 1.  Many woman think if they are wearing pants or a longer skirt that gives them wiggle room to wear a lower-cut shirt-- don't do it on the first date. Think of it as you're making him work for it. Push forth your personality and beauty before using the old "boobage" standby to hold his attention. Sure, show off some skin, but not enough so you can see  major cleavage. If anything, wear a higher neckline in a fitted shirt or dress--your breasts will be outlined, but concealed. He can imagine what they look like for the rest of the night...


I'm sorry... can you repeat that? I'm having a hard time paying attention.

Surprisingly appropriate. Girls are locked in and secure.


4. Dress a Little Nicer Than a Casual Outing with Friends. Of course, if you KNOW your date is going somewhere super fancy or very casual, then dress for that occasion. But, if this is a dinner/drinks/outing thing, don't break out the 4 inch heels and frilly dress.

I know some of you are reading this thinking, "Hey, I've got my own style, we're not going to all wear the same thing." Yes, this is true, but I think the rules are universal. Most men, unless you're going after P Diddy or Mr. "Make It Rain" want to get to know you, not promote you off in hopes that paparazzi will show up.


It's date night, not the runway


If you like dresses, wear a cute dress, but in moderation:

  • If it's one color, feel more free to have ruffles, drapery, embellishments, etc.
  • Don't wear baby pink, blue, etc. Look nice and like you accept that you're no longer a teenager
  • If it's a pattern, don't go overboard--no sequins, ruffles, flowers, loud prints
  • Stay away from floor length or super mini skirts -- this is not the red carpet
  • Keep your dress in the mid-thigh to cocktail length -- it works for many different occasions
  • Don't wear fabrics such as silk/satin unless it's a darker fabric -- it can look very formal
  • Keep the shoe simple. I'm not a sexist, but most guys don't give a DAMN about our shoes. And some of our prettier shoes hurt like hell after a few hours (minutes?) of wear. And the pain will read in that scowl on your face. Pair this with a simpler black heel or your favorite pair of flats.

Denim, the universal blood type of couture:



  • Denim is fabulous, and can carry you through a casual day or a sleek night out
  • Plus-sizers are not created equal. Although I'm not one of them, so of us have AMAZING, fit, great legs. Show them off! If you can rock a skinny jean, buy a dark denim pair and make that your date-night staple. Fit with a number of dressy tops and a pair of black heels or a nice pair of flats. 
  • If your legs are not one of your most-loved body parts, try a boot cut or straight leg. It will hug your curves and give your leg a nice elongated shape. Same rules apply, find a dress top--maybe with some shiny embellishments-- and a black heel or nice pair of flats.

Tops, Blouses, Tanks:

Technically a tank, with great design & neckline Available at Macy's here.
  • I'm not a school marm, but I don't like the idea of wearing a simple ribbed tank top on a date. HOWEVER, if that "tank" is a little altered by shiny embellishment, thicker straps, interesting design or cut on a bias that is a different story. Wearing a tank, will show off some skin (your arms) without revealing too much cleavage. Yes, pick a tank that doesn't cut too low
  • If you don't feel comfortable showing your arms, why not wear a dressier top with a cap, 3/4 length sleeve OR a one-shoulder top

My last issue is jewelry--since so many women feel different about jewelry, I will lay off this subject for the most part. However, don't overdo it. Wear one bracelet, one necklace, non-obnoxious earrings.

The point of a date is to let him get to know you, not the barrage of accessories and layers and masks we all wear. Be you. That way, if he ever has the audacious to call you crazy at some point in your relationship you can honestly say you were always genuine and he knew what he was getting into. :) Happy dating!


LadyJ can be found at: http://ladyjwanderlust.blogspot.com or on Twitter at @LadyJWanderlust


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