How To Wear: Casual Cocktail Attire
How To Dress in Casual Cocktail Attire
Written by Kim Tregonig
Imagine this: you're walking through the charming streets of small-town Saskatchewan, Canada, surrounded by the vast expanse of the prairies. It's a place that feels straight out of a postcard, with a name so quirky it's impossible to forget. (this is where I am originally from) And let me tell you, the folks here are as passionate about their football as they come, proudly sporting green for their beloved Roughriders. Plus, if you ever need a helping hand, you can count on them, no questions asked.
Now, let's chat about something we can all relate to: fashion. Growing up in a remote area like this, our style options were about as limited as the channels on an old TV. We're talking Sears catalog or bust unless you feel like embarking on a two-hour journey in search of something different. Standing out wasn't exactly encouraged; blending in was the name of the game, even if it meant sacrificing our unique flair. And trust me, every town had its fashion vibe, a silent language that spoke volumes without saying a word.
But here's the kicker: this whole fitting-in thing isn't just a small-town struggle. Nope, it's a worldwide phenomenon. Whether you're strutting the streets of a big city or chilling in a quaint village, we all wanna fit in, right? Sure, there are those brave souls who rock whatever they please, but even they have their moments of doubt, hitting up their crew for outfit advice or sliding into those group chats for a bit of fashion INSP.
So, my friend, if you've ever felt lost in the fashion maze, fear not! This article is your go-to guide, your cheat sheet to cracking the code of social style when it comes to what to wear when casual cocktail attire is needed. With this newfound wisdom, you'll stroll into any event like you own the place, rocking your outfit with confidence and swagger.
Cocktail attire was created in the 1900s
After people started to get tailor-made outfits for very fancy occasions.
It is not that way anymore, as it has morphed into another version called Casual Cocktail attire. This title has eased up on the formality and is requested on invitations ranging from Reunions, Charity Events, Holiday Parties, Anniversaries, Engagement Parties, Weddings, After Work Events, Work Conferences, and School Fundraisers.
Think of it as dressing between Cocktail and Business Casual. This attire is now a closet staple because every year we are invited to something where we need to dress this way.
Where to start?
BEGIN GETTING READY FOR YOUR EVENT BY TAKING A MOMENT TO UNDERSTAND...
the venue, your audience and wear something that YOU feel confident and comfortable in.
The basics you need to know is you do not have to wear a formal cocktail gown. A general rule of thumb for casual cocktail attire is that it cannot be skimpy, transparent, too short, or too long.
As you scroll you will learn how to wear ALL the options: dresses, pants, skirts, jumpsuits- that fit under this category. You can even wear jeans ONLY if they are white or, black and not distressed or faded. (more on this later!!)
TIME OF DAY:
Dressing for an event during the day is always a bit more casual compared to an evening out. Bold, bright colors suit any daytime event. Pants and sparkle are preferred for nighttime. Although these are guidelines to follow, if you're in the mood and the chosen venue allows it, switch things up and blend color and sparkle day or night—go for it! What matters most is how you feel about your look.
THE SEASON:
Dressing to suit the venue matters but so does comfort. Depending on the season your event is in layering is the best way you can cover all bases so you are not cold, uncomfortable, or, distracted. Light cardigans or linen are great layers for spring and summer. Leather or Tailored jackets are perfect for the colder months & look polished adding to your look rather than taking away because it will cover up your outfit.
Pants for casual cocktail attire.
Trousers, culottes, jumpsuits, two-piece sets, and more!
Trousers
You can wear them with an elevated tank top (as shown above leather) or a bodysuit, bold jewelry, and a shoe that is comfortable and that pops (ex. A fun color).
LOOKS FEATURED:
1. Floral Square Neckline Blouse + High-waist Black Trouser + Yellow SJP Pumps
2. Mid-rise White Trousers + Drape bodysuit + Leopard heels
3. Yellow trousers + Black body suit + Leopard Sandals
4. Black Trousers + Maroon Leather Tank Shirt + Colorful Heels
Culottes
Culottes are wide-leg short pants that look like a skirt! This clothing item 100% falls under the category of casual cocktail attire. Pairs incredibly well with sweaters & OTK boots for Fall/Winter weather or a floral blouse + heels for spring/summer.
Jumpsuits
Your jumpsuit does not have to be black and can be worn for a daytime or evening event.
There are many colorful jumpsuits that compliment your skin tone and look polished for a casual cocktail event.
Add a belt to level up your look or add fun unexpected accessories if the venue allows.
Paglamas
HUH?!? I know it is a ridiculous name, lol… Or, you can just call them a two-piece set. These two-piece glamorous sets can be purchased as a pant set or short sets.
Pair these sets with a pretty sandal, heel, wedges, sock boots, OTK Boots, or cute ankle boots.
Faux Leather Leggings/Pants
Leather Pants create an upscale, edgy chic look for any casual cocktail attire.
LOOKS FEATURED:
1. Leggings + Puffy Balloon Sleeve Blouse + Grey Velvet Sandal Heels
2. Paper Bag Leather Pants + Lace top + Rachel Zoe heels
PANTS STYLE TIP:
If you are considering a pantsuit, fancy trousers, or jumpsuit, make sure you iron it out/ steam it so you do not end up with a crumpled outfit.
If you are not comfortable with that you can send your outfit to the dry cleaners to press it for you.
Dark/Black Denim
The best choice if you are wanting to wear jeans!
You can wear white jeans or, dark jeans (do not have denim distressed, it's too casual) with a blouse that reflects the season you are in & a fun heel/sandal, bootie, or OTK (Over-The-Knee) Boot.
LOOKS FEATURED:
1. Dark Denim with an Open-back Bodysuit + Dark Jeans
2. Black Jeans + Black & White Stripe Shirt + Nude Heels + Purple Clutch.
3. Wide-leg Black Jeans + Sparkle shirt + Black Blazer + Black Heels
Casual Cocktail + Shorts
What you need to know:
The textiles of shorts you can wear are linen, polyester, wool, acrylic, silk, satin, or cotton.
Types of Shorts that look great with heels are High-waist Bermuda shorts and Mom shorts.
The main rule when dressing up your shorts for Casual Cocktail Attire is to have the length fall past the roundest part of your hip or the hem meet the middle of your hand. DO NOT WEAR SHORT shorts for Casual Cocktail Attire.
shop leather shorts here:
Casual Cocktail + Skirts
The list of skirt options is very long! You can wear Pleated skirts, Midi-skirts, Printed skirts, Pencil skirts….. Tulle, Silk, and A-line.
Examples of casual cocktail skirt attire
Notice the colors I’ve chosen for your examples are for all of the seasons.
These looks can be worn to a Bridal Shower- Wedding Reception pending on the venue
Tulle can be worn from 20-60 yrs. old. If you love it, wear it with a graphic tee. Just make sure your tee is not worn to level up your look.
I chose my pink houndstooth pencil skirt I bought 15 years ago. It is a knit skirt that can be worn on cold spring days because it is bright and warm for the cold winter weather.
If I wear it in the winter I wear tights and my OTK (Over-The-Knee) Boots for warmth.
Casual Cocktail + Dresses
The best dresses for casual cocktail attire are mid-length dresses that are A-line, straight-cut, or princess cut with a flowing hemline that falls below or at your wrist.
You can choose a fitted dress with ruching also, please note your fitted dress should NOT be skimpy— leave that for the bar or other invitations.
You can never go wrong with a black cocktail dress--that will never go out of style. You will see my leather dress that falls into this category nicely. It is great for your invitation to a swanky speakeasy bar or a winter evening sipping cocktails at a Ski Chalet.
You can also choose strapless dresses, dresses with a sweetheart or square neckline, and dresses with spaghetti straps to long sleeves, there are so many options for dresses!
STYLE TIP: Do not let your undergarments show! Wear the proper shape wear, strapless bra, and so on. Nothing is more distracting than seeing what is supposed to be hidden.
Spring/Summer Dresses
Fall/Winter Dresses
Outerwear
Outerwear is extremely important for you casual cocktail attire outfit.
Here is what to do:
Wear the correct size. Oversized is on trend right now and is not going anywhere soon. For Casual Cocktail Attire purchase your oversized outerwear at least 1 or 2 sizes smaller so it looks structured. Leave the bulky outerwear for your casual everyday looks.
KNIT SWEATER: If you are cold and want to wear a knit sweater choose a long cardigan for your layer. Make sure the knit material is not frayed or piled—keep those cozy sweaters cozy at home.
JACKETS: Choose a blazer, Moto Jacket, Kimono, or long structured jacket. The better the fit on your outerwear completes your look and does not overwhelm you.
SHOP Outerwear here:
Dex Plus Faux Suede Moto Jacket in Petal Pink
Dex Longline Textured Cardigan in Ivory
Dex Soft Moto Jacket In Stone-Melange
Minkpink Camilla Blazer In Black/White
1 Dress - 3 Outwear Options & Knit Example
1. Structured Jacket.
Your jackets can be any color. Colors can be opposite one another on the color wheel or complimenting.
2. Moto Jacket: These jackets are a closet staple. They are available in suede, leather, faux leather, and multiple colors. They are like a jean jacket— you need them all to expand your options!
3. Blazer: A STYLE TIP for Blazers is to make sure they fit your shoulders. If the material restricts your arms and shoulders and that bothers you, continue to hunt for another blazer that has more flexibility in its fabric.
Crop Blazers are so chic and alongside the cropped option buy a blazer that’s hem lands at the round of your hip (example featured). These styles are both Closet Essentials.
4. Knits as a Layer: This sweater is an example of a chic knit. This sweater is wool and does not pill. It’s worth the investment when you find them to buy it.
How to switch from workwear to a night out…
Plan ahead and choose an outfit for work that can easily transition from daytime to nighttime look.
Tweak your outfit suitable for your casual attire invitation by switching to bold jewelry, a different jacket/blazer, and heeled shoes to refresh your look.
Examples of Workwear Switched Into Evening Looks
1. The Pink Houndstooth Skirt stayed and I switched the Jean Jacket to a Moto Jacket. Changed my crisp white tee to a black mock-neck top & my sneakers to mid-shaft Sock boots
2. Pleated Skirt— for the evening I switched to heels & a black deep V open-back sweater
3. This Silk Skirt for Workwear I styled with an embroidered navy sweater & white heeled mules — for the evening look I switched into knee-high snakeskin boots and a fit turtleneck.
What about weddings?
Weddings are dressy. To what level of dress you take your outfit depends on the venue:
Swanky Barn Wedding:
Wear a sequin skirt + a fun top, Black midi-Gown (the hem of the dress lands at your calf). Lace- anything lace is suited
Conference Center/Hotel Wedding:
Suits or Two-piece sets are great for this venue. Any skirt, dress, and trousers.
Backyard Wedding:
Wear a fun sundress & sandals with block heels so you do not sink into the ground.
A Jumpsuit & Wedges so you have height but still walk around comfortably outdoors.
Vineyard Wedding:
Semi-formal cocktail dress. Coral and green shoes (heels matter so you are not sinking into the ground)
Destination Wedding:
Flowing Dress, Body con dress, Linen pants set. (Beach Black Strappy backless dress)
Casual Cocktail Wedding:
Wear a pencil skirt and sweater with heels or a comfortable dress that is not a gown.
Accessories
Accessories elevate and complete a look. Done incorrectly, they can just distract and take away from your look.
My husband used to own a painting business. He said when he completed a job the goal was to enhance the room. The paint on the walls made a statement in the room by showcasing the "whole" room. If only the walls stood out, then it was the wrong paint choice.
The same goes for our jewelry. We stand out when people see a complete look. The jewelry features us, not the other way around!!!
LET'S TALK ABOUT IT ALL: EARRINGS, BRACELETS, NECKLACES TO PURSES...
Wear your rose gold, gold, silver, and bronze jewelry altogether. With this fad be sure to stick to the metals that work best with your skin tone to compliment you!
A bold cuff on your wrist is so chic and perfect for casual cocktail attire paired with a t-shirt, dark jeans, heels, and blazer!!
A bold earring and a clutch are the perfect accessories making any casual look stand out.
Note: A clutch is a smaller purse that you hold in your hand.
STYLE TIP: Do NOT overdo your accessories. If you layer your bracelets then add small earrings and maybe one ring.
If you choose to layer your necklaces then do not choose a bold earring.
Pick 1 part of your body to adorn and leave the rest for subtle icing. Too much accessorizing takes away from the entire look!
PURSES: Keep your large bags at home. Instead, choose to wear a clutch or a cross-body purse with a chain strap or one that is not casual so you are hands-free while mingling.
Footwear
Perfect footwear options are...
… platform heels, wedges, heel ankle boots. OTK boots, block heels, strappy heeled sandals with a thin/block heel, or pumps, plus they enhance your silhouette.
SHOE STYLE TIPS:
When wearing pants have the hem of your pants fall on your toe cleavage and just touch or, barely touch the ground. Have your look altered to achieve this look. It looks expensive no matter the actual cost of your outfit.
When choosing shoes with your dresses & skirts the options are pretty endless. I always suggest a pointed-toe shoe or slightly rounded point as it looks more dressed up.
If you want to wear an ankle boot with your dresses make sure the boot shaft does not land at the roundest part of your calf as it will make your legs look larger and therefore take away from your look. If you have larger calves please choose a sexy heel or OTK boot.
Keep your flip-flops at home—there is no version of a flip-flop that falls under this Casual Cocktail Attire.