13 Valuable Tips on Dressing for Festive Occasions

This time of year when calendars are marked by a variety of celebrations – think June graduations, charity benefits & backyard barbecues. Here are 13 Valuable Tips on Dressing for Festive Occasions.

While we welcome almost any occasion to dress up, we may find ourselves yelling, “What the hell am I going to wear?”

A well fitted dress is the best weapon in your closet

The dress reigns this time of year. Think sexy strappy, chic tailored, ultra-feminine florals, pastels & crisp white; there is a perfect dress for every event. When you step into one, you feel the excitement of the party, celebration or rendezvous.

The dress you wear will set the mood, so choose with care:

  • Is it appropriate for the occasion?
  • How does the dress move & drapes on your body?
  • Most important, does it make you feel glorious wearing it?

13 Valuable Tips on Dressing for Festive Occasions

  1. Many hosts will add the expected attire on the invitation. If it’s not included send a quick DM to your host right away! As the event gets closer they will be too busy to respond to questions. No response? Try searching your type of event in Google images or Pinterest for ideas.
  2. Three weeks before
    * Try-on your top 3 outfit choices & make sure they fit.
    * Have major skin, body & teeth treatments done; allow time for things to settle.
    * Schedule your mani-pedi for the day before your event.
  3. Take items in need of cleaning or repair to your favorite vendor(s) right away! Ever receive your garment back from the dry cleaner the day of your event & they didn’t get out the stain? So YES, RIGHT AWAY!
  4. Once your garment(s), etc. have been returned, start thinking about accessories. Make sure they not only compliment the outfit, but are appropriate for the occasion. Save your big hat for a picnic, not a red carpet movie premier.
  5. Make sure you have the proper undergarments for each look. Do you need a NEW shaper, thong or strapless bra due to wear? See BONUS below.
  6. Shoe selection is easier than you think. Will you be standing or siting? Is it an indoor or outdoor event? Pavement, grass, gravel, wood or tile floors? All these things should factor into your shoe selection.
  7. Don’t forget hair & makeup options. The same considerations for your shoe’s should be given to your hair & makeup. For example, Don’t do a full-beat of makeup for an outdoor event knowing how often touch-ups are required. PRO TIP: Draw face/hair charts. HERE is a great site on how to create a pro-level face chart!
  8. Outerwear is usually an after thought in hotter months, but most indoor events are air conditioned. Oversized blazers are still trending & can be found in the men’s section of your local thrift store. Need a light cover-up for your Hampton’s beach party? Try a lace shawl; it can be tied in a multitude of ways.
  9. A week before your event have your hair trimmed & deep conditioned for maximum results.
  10. Three days before
    * Try-on all 3 outfits & take pics. Practice Coco Chanel’s rule, “Before you leave the house,
    take one thing off!”.
    * Attempt to create the conditions of your event & test each outfit. Don’t forget pics; post
    them on social & get opinions.
    ο Invited to an outdoor picnic? Go outside in a grassy area & make sure you can sit on
    the ground comfortably.
    ο Wearing new shoes to a charity gala? Try walking in your bathroom to recreate a
    tiled floor.
    ο Your closest playground can mimic a beach, if it has a sand pit or area.
  11. Two days before
    * Do hair & makeup trials. This helps your “day-of” timeline & figure out how you will get
    into your outfit once your hair & makeup are done.
  12. Day before
    * Check the weather
    * Make your final selection on outfit, accessories, makeup & hair
    * Go to your nail appointment
    * Make a day-of timeline (include items below)
    * Get a good night sleep
  13. Day-of event
    * Do a final weather check
    * Make last minute adjustments
    * Take tons of pics of social media
    * HAVE FUN!

What to Wear by Event

Below is a list of events according to realsimple.com & I included picture suggestions (mostly) from the 2023 S/S collections.

Formal Events

Baptism, Bar Mitzvah, or Other Religious Ceremony

Rely on a pretty daytime dress, or a suit paired with feminine underpinnings & accents. Avoid anything low cut, short, or clingy, and bring a light sweater, blazer, or neat jacket to cover up sleeveless styles. If there’s a reception immediately following the ceremony, and no time to change in between, wear a cocktail dress or dressy pants with a jacket to cover up in the temple or church.

Black-Tie Wedding or Charity Gala

Think tuxedos, shimmery fabrics, and ornate details. While etiquette rules are softening on the question of dress length, your best bet is a tea- or floor-length gown. A column or A-line dress is most sophisticated, but you could wear a well-tailored, formal suit. Now’s the time to elevate your look with elegant jewelry, fabulous shoes, and a great hairstyle.

If the invite says “black tie optional,” you can feel free to loosen up slightly. For example, a formal knee-length cocktail dress is appropriate if you don’t own a long gown.

Cocktail Party, Engagement Party, and Most Weddings

The party dress code for one of these relatively fancy events will likely be “cocktail attire”. So opt for a cocktail dress—you can’t go wrong with a little black dress. You can also mix it up with dressy separates.

These days, a cocktail party can be anything from a swanky society affair (cue that glittery knee-length number) to a low-key group of friends gathered around a platter of appetizers.

For the most part cocktail parties are dressy-casual. Avoid fabrics that are too casual, like chino, jersey, and denim. Also, stay away from super-short styles. Try a detailed top with a knee-length skirt or tailored pants + sexy heels or fancy flats.

One more thing to note is different cities have their own dress codes. No need to overthink it, but it’s good to keep in mind.

“Cocktail attire in Miami is just as dressy and chic as in New York, regardless of the weather differences, while in San Diego, it’s interpreted a bit more casually because the city is relaxed,” says Lauren A. Rothman, founder of Style Auteur, a fashion-consulting firm based in Washington, D.C.

Holiday Party, Dinner Party, or “Festive Attire” Event

These occasions let you push the limits on glitz and color. So, in essence, almost anything goes, as long as it’s nice enough to suit the venue and occasion. SUGGESTIONS: an outrageously colorful dress, a sleek jumpsuit, a festive top paired with a fun midi-skirt or palazzo pants. Have fun with a statement necklace or earrings that wow. BONUS: rock textured embellishments, like feathers, tassels, lace, sequins, beading, or bows.

Casual Events 

Outdoor, Day, or More Casual Wedding

Assuming an outdoor wedding is happening when the weather’s warm, opt for a flowy sundress, a glam maxi dress, or a stylish shift dress. It’s not that black isn’t allowed, but lighter and brighter shades—and splashy patterns—often feel more appropriate. Also, shoot for shades that complement the natural surroundings, like blues, greens, yellows, and coral. Finally, when it comes to shoes, stick with flat soles for any event where you’ll be either on a lawn or beach.

For day weddings, which tend to be more casual, steer clear of anything heavily beaded or sequined. Instead, opt for a knee-length dress in a material like cotton; in warmer weather or regions, strapless styles and open-toed shoes get the nod of approval.

Bridal Shower or Baby Shower

A flattering, feminine dress, printed skirt and sweater, or a fun pair of pants and a flowy top works great for showers. Wear shoes you’re comfortable in (heels or flats), if it’s chilly out opt for cute booties. Bridal showers follow similar rules to a wedding; wearing white should be reserved for the bride unless she or the shower hosts specify otherwise. Black isn’t forbidden, but make sure it leans more on the side of chic than somber.

Family Get-Together, Barbecue, or Birthday Party

Go laid-back with a pair of nice jeans, a fun top, and stylish sneakers, sandals, or flats. Relaxed vibes are great, but before you get too comfortable, leave the yoga pants, graphic tees, and worse-for-wear sneakers at home. Instead, take a cue from the host; if they’re always dressed to impress, put some effort into your look, too.

On a Cruise

Your chosen cruise line will most likely have a website with what to pack for your trip + specific dining & event dress codes.

During the Day

For a warm-weather cruise, pack what you would for a warm beach vacation: shorts, breezy shirts, sundresses, skirts, bathing suits, coverups, sandals, and sneakers.

For a cold-weather cruise, pack a variety of things you might wear during the day on a fall or winter getaway: jeans, leggings, slacks, sweaters, sneakers, winter coat, boots, and flats (bring a bathing suit or two if there’s a hot tub or indoor pool). Be comfortable and relaxed, but aware that you’re not at home by yourself.

Many cruise ships have multiple restaurant options that range in formality, from totally casual (NO bathing suits without cover-ups, bare feet, or ripped jeans) to smart casual and formal. If there’s only one main dining room, the dress code may change throughout the cruise (casual the first night, and formal or even black-tie to celebrate the last night).

In the Evening

Bring a few dinner outfit options. You can’t go wrong with a knee-length sundress or clean white jeans and a nice top paired with sandals or flats for a casual dinner.

Step it up with nice pants (in place of white denim), elegant jewelry, and a pair of wedges or chunky heels for a smart-casual night.

Fancy tea- or floor-length dresses, heels, and a pretty wrap work perfectly for formal nights. Many cruises have a black-tie dinner, in which case, go ahead and dress to the nines.

Career Related Functions

Job Interview

Keep it clean, professional, and appropriate. Pumps and a tailored suit (pants or skirt) or simple black or navy dress always work great as a job interview outfit. These tend to be the standard for most corporate companies, although if you’re job-searching in a more laid-back industry, like at a tech startup, design firm, or hip magazine, feel free to express your personal style.

Veering too trendy or casual can be off-putting. Steer clear of jangly, distracting jewelry, and avoid denim. Even if the prospective company’s dress code is casual; you should always be more dressed up than the people who work there.


Don’t overthink what to wear to a graduation event. Think nice and neat but not super dressy. A knee-length white, colorful, or floral dress is a great option.

If you’re the graduate, don’t put on anything you’ll regret wearing in tons of graduation photos or celebratory lunch with your grandparents. Wear comfortable heels, flats, wedges, or nice sandals to walk across the stage smoothly.

For someone else’s graduation, follow similar guidelines as above, or as you would for a springtime baptism, bar mitzvah, or Easter celebration: neat, fun, and thoughtful, but not overly fancy.

Try chic, cropped pants with a nice top, a pretty patterned skirt, or a cheerful sundress made with nice fabric. Many graduations occur in late spring or early summer and often involve sitting outside for long grad ceremonies, so mind the weather. You might be sweltering hot in long sleeves or pants, so opt for a breezy A-line dress or skirt to keep cool. If it’s raining, you may be moved to an over-air-conditioned auditorium or gymnasium, so bring a wrap or sweater to keep from freezing.

Business Dinner, Work Party, or Networking Event

One adjective to give you direction: polished. When you’re dressing for a work function, the culture of your office should prevail. If it’s a conservative environment, dress conservatively for events, too.

Go a step up from what you’d wear to the office. Wear a pretty necklace or blouse with your suit, or try a skirt and heels instead of pants and flats. You know your company dress code best, but again, err on the conservative side, especially if you’re mingling with clients or work superiors.

For a casual outing, like the company picnic or charity 3K run, it’s OK to dress comfortably for the activities on the itinerary. Just skip anything questionable or provocative: super-revealing tank tops, barely-there ripped denim shorts, or T-shirts with eyebrow-raising messaging or graphics.

Funeral or Wake

A safe route for what to wear to a funeral is usually a pantsuit or knee-length dress with a cardigan or jacket on top. Jewelry should be quiet and refined (simple studs and a minimalist pendant necklace). This is not the time to look flashy or trendy; keep it neat, respectful, and modest (unless you’ve been told otherwise).

As for color, black is a standard choice but not mandatory. What’s most important is to convey the solemnity of the event, which can be accomplished with toned-down clothing in dark neutrals, like navy, brown, and forest green. Dark & discrete patterns are also perfectly acceptable.


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