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Fashion Reviews Style

The Great Cocktail Dress Search


So I am not by nature a fancy person ~ give me a Dollar Tree wine glass, an Aldi wine varietal and a pair of sweatpants and I’d call that a successful Saturday night ~ but through my full-time job, I have some occasions that require bumping up the fancy quotient.  

Now can I just say for the record, that any fancy dress occasion is way harder for women.  Most guys can go to 90% of occasions with their normal shoes and hair, top it off with a shirt, tie and slacks and DONE.  There’s not a lot of room for misinterpretation with what is a tie.  But “cocktail dress” on the other hand?  We’ve got a seasonality factor, age and style of the wearer, what exact level of cocktail dress — are you joining James Bond on your yacht off the Amalfi Coast or is it a charity fundraiser in the Midwest?  You could wear a cocktail dress to both of these occasions and you could be very off on both.  It’s a real tightrope walk is all I’m going to say.  

So here are my criteria for my search (and maybe stumbling blocks you’ve run into when searching for cocktail attire too):

  1. Work appropriate but still “me” and something I would wear again
  2. Not make me look 16 or 116
  3. $100 absolute hard stop pricepoint
  4. Place with free returns (because I only order from my couch)

Here’s what I found for possibilities: 

Look #1: The Classic Little Black Dress

Cocktail dresses for women

The Try-on:  I know the little black dress is the gold standard in cocktail attire, but black has just never been my color.  It’s passable when I have a tan, but when I’m sporting my actual “pale as a ghost” skin tone roundsabout October, I channel kind of a witch vibe.  That being said, I love the cut and fit of this one and feel like even if I didn’t wear it now, an occasion would come up that would be absolutely perfect for this one.

Dress Details: Lauren, Ralph Lauren Mesh Jersey Dress, Size 14, $65 Macy’s.  Find it here.

Look #2: A Colorblock Sheath

Cocktail dresses for women

The Try-on:  Love the colorblock on this one and the length is good.  I was worried about the neckline since it’s so plunging and I didn’t want it to be a free show scenario, but somehow it’s not.  I really like the fit, but this one is just a little too much of a business vibe.  Like more of a day dress than a night dress.

Dress Details:  Vince Camuto Colorblock Sheath Dress, $88.90, Size 14, Nordstrom.  Find it here.

Look #3 A Gorgeous Fall Midi Dress

Cocktail dresses for women

The Try-on: I was excited about this one — I love a bright pink and like how it’s understated here with the plum.  I was a little nervous about the midi length as that can be a tricky length to pull off and has made me look really stump-legged in the past.  Nope!  This is the swishy skirt of my 1950’s dreams.  The fit is great and I love, love, love this one! Bonus: it’s a really heavy stretchy knit and just feels amazing on.

Dress Details: Eliza J Contrast Hem Sleeveless Midi Dress $88.90, Size 14, Nordstrom.  Find it here.

Look #4 A Calvin Klein Off the Shoulder Number

Cocktail dresses for women

The Try-on:  Love the just below the knee hemline here and also love that it’s an off the shoulder dress that really doesn’t require a strapless bra.  I feel like it’s right on the work appropriateness line, but not pushing it too much.  But it does show allllll the things on me.  The material is kind of a scuba, but not super thick, so I’m just not sure.  On the fence on this one!

Dress Details:  Calvin Klein Off the Shoulder Dress, $48.99, Size 14, Macy’s.  Find it here.

Look #5 A Classic Lace Sheath

Cocktail dresses for women

The Try-on: This one has definite possibilities.  It’s a great stretchy lace, has some shimmer too it without looking like I’m trying to attend the prom 20 years too late.  It’s a little shorter hemline, but not overly so and it’s a great fit.  Love lace, but not when it’s stiff as a board — this was a perfectly stretchy stretch.

Dress Details: Nightway Metallic Lace Sheath Dress, $45.78, Size 14, Macy’s.  Find it here.

Look #6 A Wildcard Jumpsuit

Cocktail dresses for women

The Try-on:  So I almost did not push “add to cart” on this one.  I love how jumpsuits look … on other people.  Maybe it’s because I’m taller, but a lot of jumpsuits fit me in a real leotard type fashion.  Umm, not a good look.  I’m so, so glad I tried this one though.  It’s a great fit, not too tight on the torso length and it just felt swishy and cool.  

Dress Details:  Tahari Tie Waist Crepe Jumpsuit, $95, Size 14, Nordstrom.  Find it here.

So luckily, Nordstrom and Macy’s are great on returns so I think I’m going to let these all just marinate in my closet as the occasions come up and see what’s the final final winner at the time.  The short list is definitely the jumpsuit, the midi plum dress and the lace dress!  Any great places to shop for formal looks that I missed?  Tell me in the comments!

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3 Comment

  1. Wow!! I loved every single one!! Seriously, each pick was amazing 🤩 I don’t even know that I could pick a favorite! Not fancy over here either, but this line up makes me want to be!!

  2. I’m really grateful you did this! You’re the size that many women could relate to and you did an amazing job modeling! Thank you!!

    1. Thank you so much! I think it’s important to see a variety of sizes out there and I truly appreciate your comment so much 🙂

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