A party invitation brings promised merriment along with a tricky question: What to wear? If the note specifies “cocktail attire,” sartorial stress could be right around the corner. This term rarely has a clear definition, and you’ll find it used in situations from weddings to business events.
We asked a group of well-dressed men and women—designers, stylists and fashionable founders—to provide guidance on what cocktail attitude means now. They also shared the labels, embellishments and silhouettes they reached for when the invites started piling up. Here, insider-tested ideas to consider when getting ready for your next evening out.
1. Opt for bright, bold prints when you’re not sure how dressy to go
Silk Long-Sleeve Maxi Dress
Marina Larroudé, a New York City-based former fashion editor and co-founder of Larroudesays her “go-to brand for cocktail wear” is the “festive, unpredictable” La DoubleJ because the pieces “always make a statement.” this dress above turns a simple silhouette into something appropriate party via heavier silk-twill and graphic oversized flowers.
Printed Silk Swing Maxi Dress
The multicolored spots of this La DoubleJ “flattering” maxi are “whimsical and sophisticated,” says Larroudé. The maxi could “go both ways” and be dressed up or down for an event. “I’m planning on wearing it with gold platform sandals” for “extra inches,” she adds.
Flower Oval Cabochon and Crystal Earrings
Dramatic earrings can quickly elevate a simple dress—or easily be removed if you arrive at a party and feel your look is too formal.
Mini Feather Pouch
One key to cocktail attire, according to Palm Beach, Fla. -based Sarah Bray-West, a style writer and founder of an eponymous line of sun hats, is to add “something unique with a dash of character and flair.” Accessories like this chain-strap bag that show just “a touch of feathers” are a way to inject a bit of stylish whimsy.
2. Choose fabrics and cuts that aren’t traditionally formal
Casual cotton is most definitely acceptable as cocktail attire, per Bray-West, especially in warmer climates. She skips heavy or formal fabrics when at her home in Bermuda because “everything is significantly more laid-back—heels are not a thing!” The simple shape and lightweight fabric of this dress is “intentionally effortless.” She would wear it with her hair tied back and minimal makeup to complement the relaxed vibe.
Bray-West, whose signature style is retro-glam, often wears caftans for cocktail hour, which she picks up at vintage stores in Palm Beach and Houston. Her favorite silhouette—a column shape and wide sleeves that stop at the wrist—can be found in current-season styles like this embroidered Tory Burch piece.
3. Swap in tailored separates for a dress
Double-Breasted Sateen Blazer
Sateen Straight-Leg Pants
Cocktail attire doesn’t have to mean a cocktail dress. “I really lean into suits—they work in almost any cocktail moment without feeling overdone,” says Meg Strachan, the Los Angeles-based founder and CEO of jewelry brand Dorsey. She prefers a matched set in black or off-white like this blazers and pants one from insider-loved label Toteme, but “literally any color works.” The lively velvet combo below is a brightly festive option.
Willa Blazer in Tipped Stretch Velvet
Full-Length Kate Straight-Leg Pant in Stretch Velvet
4. Layer a jacket for personality
To add panache to a little black dress, Bray-West “pairs it with a statement jacket” like this brocade option. The dark-ground floral has an after-dark, rock ‘n’ roll vibe—the print was inspired by Jimi Hendrix, the brand notes.
Oversized Double-Breasted Tux Blazer
If bold patterns aren’t your thing, use volume for drama. Strachan “lives for evenings in an oversized blazer” like this double-breasted style. She wears it over “a great tuxedo shirt” from her go-to label Chava Studioswhich features classic design elements like a bib front and wide cuffs.
5. Experiment with feathers for a fun touch
Etta Feather-Trimmed Knitted Mini Dress
What is a cocktail attire if not “an opportunity to dress up, play with clothes and have fun,” says Larroudé. This season she’s shopping for pieces with feathers like this fluff-trimmed mini dress. The subtle feather trim at the hem and bustline are the exact right amount of fluff, says Bray-West.
Ostrich Feather Bustier
A festive top and trousers provide an alternative to the ubiquitous cocktail dress. Larroude would wear this feathery bustier with printed pants or jeans for a dressed-up dinner: “It’s so celebratory—the perfect look.”
6. For men, stick with a suit
Black Havana Jacket
One fail-safe, cocktail-attire combination for men is “a black suit, white shirt and no tie,” says Cash Lawless, a sought-after hairstylist who also advises on investment strategies as The Millionaire Hairstylist. He almost exclusively wears “double-breasted suits with early American features like large peak lapels,” including the above version from Suit Supply.
Double Breasted Suit Jacket
Classic silhouettes in bold colors are a favorite of Robert Denning, the New York City-based co-founder of sunglass brand Westward Leaning. “My go-to look is a cool Zara suit in a striking color—it makes a statement.” He’s recently worn “a bright cobalt, ultra-wide-legged suit” and “a double-breasted, blush pink” version similar to the option above. He also eschews traditional footwear, pairing the suit with white Nike high-topsthough they “need to be super clean to qualify as cocktail attire.”
Undercover Air Force 1 Rubber-Trimmed Leather Sneakers
7. Build on a base of classics
Men’s Slim-Fit Non-Iron Performance Herringbone French Cuff Dress Shirt
For shirting, Lawless prefers a “French cuff and links,” since both “push the look past business attire.” His go-to is the slim-fit dress shirt from Calvin Klein. This version from the label’s Steel range uses a wicking performance fabric that helps avoid sweat marks. As for cuff links, he likes to hunt for art deco treasures on eBay.
ATM Anthony Thomas Melillo
Short-Sleeve Regular Fit Stretch T-Shirt
The fashion-forward look Denning preferences is reflected in his choice of under layer too. He “always wears a high-end T-shirt underneath” like this luxurious stretch-cotton option. His overall cocktail attitude guidance? Don’t worry too much about following fashion rules: “Cocktail attire is about asking someone to make an effort.”
The advice, recommendations or rankings expressed in this article are those of the Buy Side from the WSJ editorial team, and have not been reviewed or endorsed by our commercial partners.