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So much of the world has gone more casual in the past decade – from Michelle Obama’s famous pantyhose avoidance, to the athleisure “workwear” that became ubiquitous during the pandemic and subsequent work-from-home era – that it’s easy to forget how to dress up. (Or, for that matter, that choosing the perfect dress is even a thing!)

But some occasions – from proms, school formals, and quinceañeras to weddings and fancy parties – still require a level of attire that’s several notches above this mama’s day-to-day standard. So whether you need a refresher course for yourself for that summer formal wedding attire, you’re heading prom dresses shopping, or you’re going formal dress shopping with your daughter for another big occasion, it’s a good time to revisit the dress shopping rules and dress selection tips that will make your lives easier and less stressful while hunting for that special dress.

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Shopping for Special Occasion Dresses, from Prom Dresses Shopping to Wedding Guest Attire

1. Know (and understand!) the dress code

Before you even start shopping for special occasion dresses, it’s important to understand what you’re shopping for. Which can be harder nowadays than, for example, last century when prom gowns were automatically tea length to floor length.

Dressing for high school and college “formals” generally means suits or tuxes for the guys, and can mean longer gowns for the ladies. Similarly, quinceañera and debutante or cotillion dresses tend be “floor length,” hitting no higher than around one’s ankles. However, I’ve also seen a lot of girls wearing short above-the-knee dresses to school “formals” (including prom) at my kids’ schools in recent years.
“Cocktail dresses” and other “semiformal” options also vary in length, though these tend to be anything from mid-calf on up. A more upscale cocktail dress for grownups is often “tea length,” or falling anywhere from mid-calf to mid-knee; for high school and college students, semiformal options can be mid-knee or even higher.
For wedding guests, it’s important to read the invitation carefully, both for any direct indicators from the bride on the dress code for her wedding day and for subtler cues like time of day and wedding location. The more traditional the location (i.e., house of worship vs. city hall) and the later in the day, usually the more formal the attire expectations for the guests. When in doubt, you can always ask!

2. Consider how much lead time you’ll need, and plan accordingly

This will vary from event to event, and also depend on certain other factors like your/your daughter’s role in the event. If you’re shopping as part of a wedding party (or a critical guest like mother of the bride or soloist/reader), finding the right outfit will take longer. (The good news is, the more central a role you’ll play, the more likely the bride will help coordinate your dress choice process.)

On the other hand, you may have your own special factors to consider. For example, bridesmaids who are pregnant will need to account for their ever-changing waistline as part of their dress-shopping process. Either way, you’ll need to factor in time for shipping and alterations, so we’re generally talking months of planning time. Granted, my college roomie had my mama doing final alterations on my and the other roomie’s bridesmaid dresses barely 24 hours before her wedding. But unless you have a seamstress on hand, assume that even “last-minute” alterations will take a minimum of weeks to execute.

For college and high school special occasions, chances are good that your daughter will be buying something off the rack with few alterations needed. In this case, you shouldn’t need more than a month or two of lead time, and hopefully any alteration needs will be minimal. This is a good example of where the “law of natural consequences” comes into effect; the sooner your daughter wants to get started, the more time and choices she’ll have. Waiting until the last minute will limit her options, which is a natural consequence of how things played out. Follow her lead on this one.

3. What to wear when shopping for special occasion dresses

Formal dress shopping works best as a planned outing vs. a spur-of-the-moment activity. Especially if your daughter lives in sports bras (as mine do), then you’ll want to make sure she’s got her best bra on, preferably one without a Y- or T-back (unless that’s the style of dress she’s going for). If your daughter has a different genetic makeup than my, er, well-endowed genetic profile, she may be lucky enough to get away without a bra; I’d recommend doing some jump and jiggle tests in the dressing room to make sure she’s not going to fall out of the dress. (And keep in mind, both for you and for her, that there are always longline, strapless, and convertible-strap bras available in department and specialty lingerie stores.)

If she already knows she wants to wear heels and already has some of her preferred height, it’s worth bringing those along, too. (Side note: it’s never too early to suggest healthy shoe habits, even if your suggestions fall on deaf ears. Five-inch pointed-toe stilettos may look stylish, but they’re neither good for long-term foot health, nor comfortable for dancing. Our high school’s exchange students are always aghast that American girls shed their fancy party shoes five minutes into a formal or semiformal.)

When dress-shopping for yourself, consider what will help you feel and look your best. If you already have some good shapewear to tuck in that post-baby pooch, remember to bring it along; ditto for your best and/or most comfortable underwire. And if you already know you want to wear your hair up, consider putting it in a high ponytail so you can get a sense of what necklines will look like with your hair off your shoulders.

4. What dress color works best on me?

Hopefully you or your daughter already some sense of what colors look good on you and which to avoid. Many stores still have harsh fluorescent lighting, especially in fitting rooms. Because this lighting is unflattering to so many skin tones, you’ll need to factor that in.

Another helpful shopping tip is to wear a neutral-colored (black, white, or beige) tank top when dress-shopping. Wearing a neutral top facilitates testing dress colors against skin tone and hair while still on the sales floor. Have your daughter hold different dress colors under her chin (or do this in a mirror if you’re shopping solo for yourself). Which colors make you/her look washed out or unwell? Which color dresses make you/her “glow”? Even in unflattering lighting, you should be able to get enough sense of the differences to rule out the worst colors and determine what’s most flattering.

5. How to find the right dress for your body type

The right dress cut can make all the difference in a dress that looks as if it belongs to someone else and one that looks custom-made for you. Since choosing the right dress is a great way to boost your confidence and help you relax at big events, here’s a cheat sheet for you and your daughter to consider while shopping for that knockout special occasion dress:

Empire waist dresses

Empire waist dresses have their “waistline” just below the bust, flowing loosely downward from there. This choice creates a feminine silhouette, can help to emphasize a smaller chest or flatter a slender frame in a feminine way, and is also a comfortable choice for formal dressing during pregnancy.

A-line dresses

A-line dresses are timeless and can flatter many body shapes by gently skimming the body while expanding outward at a gentle slope from the waist.

Sheath dresses

Sheath dresses are cut straight, rather than having a wider skirt, and tend to be close-fitted. A sheath dress is perfect for those with slender or hourglass figures, and should fit close to the body. For those who are pregnant or want to camouflage an extra pooch, look for a sheath dress with ruching (horizontal gathers) on one or both sides of the waist.

Hourglass shape dresses

Few choices are more feminine and flattering than a dress that highlights natural curves and emphasizes the waist; hourglass shape dresses are designed for this. While these dresses are perfect for those whose bodies tend to be wider at chest/hips and slimmer at the waist, an hourglass cut can also play up one’s curves for those body types that are less “classically” proportioned in a flattering way.

Apple shape dresses

Apple-shape dresses skim loosely over one’s middle, giving a well-proportioned appearance to one’s legs and body overall; this cut works especially well for those with wide hips and narrow busts.

Pear shape dresses

Pear-shape dresses are designed to highlight your upper body while skimming over your hips, which can help to balance and harmonize proportional appearance overall.

Rectangle shape dresses

Rectangular-cut dresses are great for those who don’t have that “classic” hourglass figure (narrower at waist, wider at hips and bust). Their straight cut can give the illusion of curves and define the waist, flattering almost any body type.

Final thoughts:

Whether you’re shopping for yourself or helping your daughter find THE dress for that special dance or party, shopping for special occasion dresses can be stressful or seamless. Common sense still applies; don’t go shopping hungry or tired if you can help it, and give yourselves plenty of time. Also keep in mind that it may take multiple stores or shopping trips to find a dress that works. Planning ahead with these tips for formal dress shopping will help you to have more fun with less stress.

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