The Ubiquitous and Essential Cocktail Dress

| Jun 26, 2017
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The Cocktail Dress is an integral part of any crossdresser’s  wardrobe given our penchant for looking pretty  while attending conferences, holiday parties and all manner of special events. Just look at any group photo and you’ll see a wide variety of outfits. But if you are new to the party scene or just want to explore some options to give you a more fabulous look or just need a change of pace, then this review may be helpful to you.

cocktail dresses

Photo Credit: Getty Images

What is Cocktail Attire?

Cocktail attire is less dressy than “formal” attire, and much more casual than “black tie.” Most commonly, cocktail attire is requested at weddings, holiday parties, retirement celebrations, school reunions, anniversary and engagement parties. The formal factor can be a pretty fabric (like satin or lace) or a bit of sparkle. And certain silhouettes — like the one-shoulder dress — are definitely ready for cocktail hour.

The key word is of course, party. Cocktail attire for women can encompass a broad range of looks that includes the classic little black dress to a more festive or colorful dress with a print/texture, or a pairing of a top and bottom. These dresses are meant to be worn for fun, dressy events that are celebratory in nature. There is a playfulness and festive attitude implied with cocktail attire such as a cute dress that hits around knee length (or shorter) with dressy details.

Any time an invitation lacks a dress code (which they so often do), you’re better off being overdressed than underdressed, as a rule. . . If you have any doubts, reach out to the host or hostess for advice.

The Cocktail Dress Silhouette

Fit’n’ Flare Dress:  Want to instantly create an hourglass figure? The fit ‘n’ flare silhouette is perfect for this. It cinches in at the waist to create the illusion of a smaller waist, but flares out at the skirt to hide a heavy lower body. Keep fabrics soft — not stiff — and avoid excess pleats for the most flattering look. The beauty of this silhouette is that it looks ladylike, but you can carry off flats or lower-heeled shoes with that full skirt (as well as high heels.)

fitnflare-one shoulder cocktail dress

L-Fit’n’ Flare Dress R-One Shoulder Dress

One Shoulder Dress:  The one-shoulder dress is also a very flattering after five dress because it draws the eye up to create a taller, slimmer figure. The one-shoulder silhouette also works well for women with broad shoulders because it breaks up the line. When the dress includes some softness (satin, ruching) it becomes a very flattering look that works on most women.

Sheath Dress: One of the most flattering — and no-fail — cocktail dresses you can wear is the sheath dress. This deceptively simple dress will make the most of your body’s natural shape and look chic and feminine at the same time. Sheath dresses with a little something extra — a cowl neck in the back, a pretty floral print, a lace fabric — are ideal for cocktail dress because it’s the type of dress that can pull double duty: most sheath dresses also work for the office (if you don’t want to show your arms, just pop on a blazer or belt a cardigan over it.)

sheath-optical illusion

L-Sheath dress R-Optical Illusion Dress

Optical Illusion Dress:  The optical illusion dress is a magical style popularized by Kate Winslet in the Stella McCartney style. The idea is a colorblock dress that creates the illusion of an impossibly curvy hourglass shape. It makes you look curvy — but slimmer — at the same time.

Peplum Dress:  Give your girly shape the boost it needs with a pretty peplum dress. This style does wonders for an athletic figure. It also looks good with curvy girls, creating an exaggerated hourglass silhouette. Whatever your shape, you can benefit from the look of a smaller waist, which the peplum dress does. Peplums with a longer “skirt” area can also cover a tummy, which makes this a miracle silhouette.

peplum and drop waist dress

L-Peplum Dress R-Drop Waist Dress

Drop Waist Dress:  Need to hide a few extra pounds? Want to look tall and slim? Try a drop-waist dress as your next cocktail dress. This type of dress is ideal for figures with a wider waistline (like many women over 40 get.) It’s also perfect for petite figures because it makes you look long and lean. And for women who are top heavy and short waisted, the drop-waist formal dress elongates your torso and balances you out

Shift Dress:  One of the easiest — and most flattering — dress shapes is the shift dress. This easy silhouette skims over the body and suggests (but doesn’t hug) your body. This slightly boxy cut is extremely forgiving since it doesn’t touch your body. Go for sparkly or metallic fabrics — either allover or with trims — to add a dressier touch to the shift. Heels will elongate the look and make you look taller and slimmer.

black shift dress

Different Types of Cocktail Dresses

Cocktail dresses come in many varieties and hemlines now, too. Your only guidelines should be that for a true cocktail party, your hemline should hit below the tips of your fingers when your arms are at rest, and should not go so far as to skim the floor. Knee-length, midi and mini dresses are all acceptable.

The Little Black Cocktail Dress: Ah, the little black dress! We’ve gone on and on before about just how essential and important the LBD is. You can find them at any price, in any silhouette and with virtually limitless design details. Whether you want lace or sequins, sheer panels or embroidery — there is an LB(C)D to suit your style. Above, some of our favorite celebrities show off just how different black cocktail dresses can be, flattering legs, arms, shoulders — whatever your favorite feature might be.

LBD cocktail dress

Emma Stone, Elizabeth Banks and Julianne Moore. Photo Credit: Anthony Harvey, Frazer Harrison, Jon Kopaloff

The Embellished Cocktail Dress: These dresses tend to be more trend-forward, but they are by far the most playful and festive cocktail dresses. An embellished cocktail dress — one with sequins, embroidery, beading or even feathered elements — is the most playful type of cocktail dress. For that reason, an embellished dress may also be the most vulnerable to the changing whims of fashion trends. If you want to embrace more fashion-forward elements, look for a timeless silhouette — like an a-line or a shift  — to extend the wearability of the dress.

Embellished Cocktail Dress

Giovanna Battaglia, Diane Kruger, and Sarah Jessica Parker. Photo Credit: Kristin Sinclair, Andrew H. Walker, Tim P. Whitby

The Lace Cocktail Dress: Lace dresses are the most feminine and potentially proper style of cocktail dresses — perfect for Easter Sunday, daytime weddings and even date night! Lace is a great choice for cocktail dresses because it is ultra-feminine. Lace is a broad term for a fabric that encompasses many different styles and looks from guipiere to crochet-style looks, so be sure that if you intend to wear lace at a cocktail event, make sure the style you’ve selected is polished and dressy.

Lace Cocktail Dress

Sandra Bullock, Emily VanCamp, and Karolina Kurkova. Photo Credit: D Dipasupil, George Pimentel, Jeff Kravitz

The A-Line Cocktail Dress: We love the flirty, glamorous silhouette of an a-line dress, they can be strapless, cap-sleeved, spaghetti strapped — you name it. Flirty, flattering and reminiscent of Dior’s New Look — the a-line cocktail dress is a classic look. With this silhouette you can go both long or short, and you’ll find both sleeved and strapless dresses, as well as halter styles and spaghetti straps. The waistline and full skirt are what sets the a-line dress apart, and it’s a flattering cut for women both with curves and those who want to create them.

A-Line Cocktail Dress

Jessica Chastain, Allison Williams and Amy Adams. Photo Credit: Getty Images: Jon Kopaloff, Michael Buckner, Andrew Walker

The Long Sleeve Cocktail Dress:  This is a trendier, fun style of cocktail dress, but it can also be incredibly elegant in a longer, midi length. The long-sleeve cocktail dress isn’t for everyone — but it’s a look we find very appealing at the moment. By showing off your legs and concealing your arms, you strike an elegant and sophisticated balance. A mini-length dress with long sleeves is perfect for women in their 20s and 30s, while a longer, knee or midi-length is perfect for women 40 and up. However, always keep in mind that suggestions like these are just that, suggestions!

Long-Sleeve Cocktail Dress

Photo Credit: Getty Images: Dominique Charriau, Frederick M. Brown, Darren Gerrish

The Strapless Cocktail Dress:  Perhaps the easiest cocktail dress silhouette to dress up for special occasions is the strapless dress. If you’ve got an hourglass figure or shoulders you love to show off, a strapless dress is a dressy, pretty option. A strapless a-line dress will be especially flattering on an hourglass figure, while a midi-length cut will look cool and modern, especially on taller women. To make the strapless look feel less dated, seek out cocktail dresses with interesting details such as architectural ruffles, embellishments and even pockets!

Strapless Cocktail Dress

Hillary Rhoda, Kirnan Shipka and Allison Williams. Photo Credit: Getty Images: D Dipasupil, George Pimentel, Kevin Mazur

How To Accessorize Your Cocktail Attire

If you think about it, your dress is really only the beginning. We have suggestions for the right bag, accessories and even tights (for the chilly season) to wear with your cocktail dress or LBD.

Getting Value for your Cocktail Dress

Most of us don’t have a ‘cocktail dress lifestyle,’ one where we’re always out in the evening and need to dress up to the nines, so for us, a cocktail dress is a big investment without great cost-per-wear benefits. Notwithstanding that we may fall in love with a particular dress (I have), here are a few hints to get better value from your purchase. Just be aware of them, but don’t let them override your decision to buy the dress of your dreams

  • Make sure it’s well constructed and looks expensive (even if it isn’t)
  • Make it simple in construction, the more detail the harder it is to change the look of the dress
  • Avoid trend based looks such as peplums which will date the dress
  • Keep it in a great dark color as black will limit you from weddings or similar events. Ideally a dark color that suits your complexion and brings out the color of your eyes will take you anywhere
  • Make sure it suits your body shape and proportions
  • Avoid fabrics that are super shiny or sparkly if you want to be able to dress it down

Here are some helpful videos on cocktail dress current trends and be sure to check the Sister House Pinterest board on Cocktail dresses for even more ideas.


Is It Possible?

If you ever ask yourself, is it really possible to look this good as a crossdresser and the answer is yes. A few of us are blessed with small statures and good genes and the ability to make the most of our assets. Check out the Stylish Crossdressers in the Sister House Dressing Room. All of these ladies are fabulous, but one, in particular, Vikki La Fontaine,  is the consummate party girl and knows how to rock a cocktail dress. In all fairness, Vikki is only 4-10 1/2 and 108 lbs and sells vintage clothes. She knows how to put an outfit together. One of my bucket list items is to get Vikki to dress me one day. But at least we can dream 🙂

Vikki La Fontaine in cocktail dresses

Vikki La Fontaine in cocktail dresses

Vikki La Fontaine in cocktail dresses

Resources for this article were  Insideoutstyleblog,

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Category: Style, Transgender Fashion


About the Author ()

Tasi was a transgender, married, lifelong crossdresser. She passed away in late 2018. She’s the founder of the Ladies of the Blue Ridge transgender group in Roanoke VA, a prolific writer, commentator and blogger including fashion articles for Tri-Ess, TG Reporter, Repartee, and Pretty T-Girls magazine. Tasi currently resides in Merida, (Yucatan) Mexico. Her new website, Sister House and her blog, the Fashionable TG Woman are dedicated to fashion and style for the transgendered woman. Tasi’s book, "Top Ten Fashion Mistakes By Crossdressers and How To Fix Them" is available on Amazon or on her site free to subscribers.

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