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Writer's pictureWhitney Wisdom

The Best Fall/Winter Wedding Guest Dresses

Updated: Apr 10


Siblings or dating?

When I was little, “Wedding Season" meant summer. We’re talkin’ matching pink bridesmaid dresses dragging on sandy shores accompanied by pastel bouquets. Nowadays, Wedding Szn is officially the fall season, AKA September-November. According to all sources (The Knot, Wedding Wire, Brides etc.) October is by far the most popular month to get married! Whether you’re into the spookiness, harvest vibes, or just mild climates, couples are finding October to be the most romantic month for a wedding! So much so, that as of 2022, 20% of USA weddings took place in October alone and 36% of weddings took place in total fall, September-November. If you know someone who is engaged and looking to start wedding planning odds are, you should be prepared for an October, September, or November wedding; with just a 13% chance that it could still be a June celebration on that Save the Date. What does this mean for us, the friends and families? Start hunting for outfits in darker colors, longer dresses, and maybe even sleeves. Tips below, as always on what I’d wear to a fall or winter wedding based on the dress code.


My favorite wedding cocktail? Shrimp.

Black Tie: Getting invited to a black tie wedding can always be daunting especially if it's black tie optional. Which in that case, it's always like do I opt in??? But, the perk of getting invited to a black tie wedding is it usually means you have to go shopping for a new floor-length gown! And what could be more fun than that? With the guys in tuxedos (or dark well-tailored suits if black tie optional) take the opportunity to rev up that old Hollywood glam. This is your moment to shine in a heavily embellished sequin number. Notice the key word in that sentence, embellished. As much as I am a glitter girl, respect the gala-like fanciness of a black tie wedding and skip the all over sequin dress that looks like it was bought for prom.

If you're wearing a dress with a slit, you must pose like this.

Elegance and sophistication are your style muses for a black tie affair. Whatever that means to you! My interpretation: a sleeveless, slitted, black gown with a deep v-neck that’s not quite plunging. With the bronze and gold shooting star beading, I felt like a necklace would be overkill. I pulled my hair back into a bun to keep the glam simple. Long gold stick earrings and my most formal diamond bracelet were added for shine.


A black tie affair.

Cocktail: Is the most common wedding dress code but, what does “cocktail attire” really mean? Like I was saying in the black tie section, the level of formal-ness for womens wedding guest dresses is typically judged on the length of the dress. Knee-length, midi, tea-length gowns, and jumpsuits are all appropriate. So basically dresses cut right above the knee to ankle length and anything in between! Brown has proved to have more than a fleeting moment in fashion and beauty (Hello, brownie glazed lips.) so I took advantage and rocked one of my favorite colors in a shoulders to ankle in liquid bronze sheen dress. Crumb catcher necklines flatter your bust and for those who don’t have one it creates the illusion of a bust. I loved the ribbon sewed onto where high waisted jeans would hit. I tied it into a bow on the side for a femme touch but it could also be knotted with the ribbons cascading down the back.

Fall at its finest!

In a solid color dress, you have more of an opportunity to go all out with hair and accessories. As someone who is not skilled at doing hair, my go-to wedding guest hair is curled with the sides pulled back into a small ponytail that I twist into what looks like a little rose bud. I secure with 2 bobby pins in an X format and loads of hairspray. For shoes, I wear my most comfy heels that are heavily padded so I never have to go barefoot. My favorite strappy black pair (pictured) are Life Stride by Boscov’s. Everyone is shocked to hear that! I kept the makeup simple but I am always a fan of a cranberry lip, especially for fall!


All the shiny details make a solid color, dark dress so fun!

Semi-Formal: When the invite comes in saying “semi-formal” that kind of means anything goes. Really the bride and groom want everyone to be comfy and not to spend a ton on a new fancy outfit. For this type of event, shorter, knee-length dresses are the move! Think Homecoming for grown ups, if that is something that even makes sense. I always find long sleeve dresses to be super unexpected and unique! Perfect for the brisk fall air and less likely to require sticky boobs, double sided tape, and all the other ways us women get our dresses to cling to our bodies just so. I wore a black mesh long sleeve with patches of swirled black sequins. The body of the dress had a red and white floral underlay that would be so fun for a winter or Christmas time wedding as well!

A fall beach wedding has become a major trend! And with good reason.

I filled in the lower neckline with a long necklace plus, I added geometric hoops! I pulled my hair back into a tight and sophisticated ponytail. I know a lot of people associate ponytails more with workout and less with formalwear but as long as you take the time to smooth your flyaways I think a ponytail look is a classic way to highlight your collarbone region - including statement necklaces and earrings. If you feel self-conscious about wearing a ponytail to a wedding, leave some hair out of the hair tie and wrap it around to cover the hair tie. Hold in place with bobby pins, hairspray, and be prepared to dance the night away!


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