Fall & Winter Wedding Style

I love weddings, but when you’re invited to attend 6-10 each yeah, the task of picking out the best outfits can be a bit daunting. If you live in an area that experiences 4 distinct seasons, this can be a bit more challenging. Finding a great dress for a wedding can be tricky, but there’s a lot of beautiful options out there that will work for casual or more formal nuptials. Once you have a dress or two that works perfectly in Spring/Summer or Fall/Winter that can make things a lot easier (and cheaper), and you can change up the look with different shoes or accessories. By choosing a classic style that’s evergreen and can last for a few years, you can have a little fun re-styling your dress with jewelry or new heels.

With a wedding last weekend and our last wedding of this season happening this coming weekend, I have been thinking a lot about picking the perfect dress for a Fall wedding. I’ve also been thinking about what I would choose if we had a wedding later in the season. With the ever-changing weather in Wisconsin, it can be particularly difficult to piece together the perfect wedding guest ensemble for this time of year. Even on the warmer days, now that it’s “officially” Fall, I do find it hard to choose a sleeveless, summery dress for this time of year.

If you’ve got a wedding coming up, here’s a few tips for choosing the perfect outfit, including a few of my favorite picks.

Colors: Focus on Fall Hues & Prints.

For me, Fall is all about deep jewel tones, fall florals, and animal prints. I am loving berry, jade, burgundy, and ochre hues this season, and I found a few gorgeous options that would be perfect. I also find that depending on the wedding and requested attire, late season weddings are the best time to get away with wearing black or darker tones to a wedding. If you’re attending a NYE wedding, don’t be scared to bring out the gold and silver sequins or glitter.

Shop Dresses: Express Chiffon Long-Sleeve Sash Dress  / J.Crew Button Front A-Line Midi Dress / J.Crew Long Sleeve DressExpress Pleated Surplice Front Midi Dress / BR Print Midi DressJ.Crew Ruffle Hem Sheath Dress / J.Crew Ruffle Sleeve High Neck Mini DressBR Velvet Twisted Dress / Express Open Back Sequin Bodycon Dress


Silhouette: Not a Dress Gal, Try A Jumpsuit.

I also love that the jumpsuit trend is going strong, because we all know how comfortable and chic a jumpsuit can be for a night out or special event. I love how this piece has transitioned into the Fall/Winter with with short or long-sleeved options, lovely lace details, and in velvet, which is one of my favorite fabrics for the season. I also love the wide leg jumpsuits that are available, just pair with cute heels and you’re ready to go.

Shop Jumpsuits: Express Lace Bodice Open Back Jumpsuit / BR Cowl Neck Velvet Jumpsuit / Express Wrap Front Tie Wide Leg Jumpsuit


Length: Maxi or Midi over Mini

Though I typically opt for a knee-length or midi dress regardless of the time of year for weddings, if you don’t it’s a great time to try out a longer dress. With gorgeous A-line choices, ruffle hems, or wrap front maxis, there’s plenty of elegant options for your next event.

Shop Dresses: BR Ponte Midi Dress With Slit / BR Flutter-Sleeve Midi Dress / Express Snakeskin Print Side Tie Midi Wrap Dress / BR Floral Ruffle Maxi Dress / J.Crew Ruffle Hem Sheath Dress


Layers: Jacket Bliss

Besides just for the wedding, it’s a great time to grab a dressy jacket to pair well with dresses, skirts, or jeans. I love adding some edge with a chic moto jacket, or layering in some texture with a soft wool or faux fur. Teddy coats are here to stay (yay!) for this season, and I love the idea of adding a cute one in a gorgeous Fall color to complete your outfit. Though you won’t be wearing it all night, I find that having a great jacket to wear over my wedding guest look makes me feel more coordinated and stylish.

Shop Jackets: Express Long Moto Jacket / Express Long Belted Wool-Blend Wrap Coat / Express Belted Soft Trench Coat / Express Vegan Leather Double Peplum Moto Jacket / Express Asymmetrical Zip Faux Fur Moto Jacket / Express Cozy Teddy Jacket


Shoes: Open vs. Closed Toes

Choosing shoes for a day that you’ll spend moving about, mingling, and likely dancing the night away can be tricky. Depending on the weather, your go-to open-toed sandals might work for you, but when the temps drop, switching over to closed toes might be your best option. I love the idea of pairing a dress with a cute pair of ankle booties or knee-high boots. The mule trend is a favorite of mine and is going strong into Fall, so a pair of heeled mules in a seasonal color or animal print are always a stylish choice. If the wedding calls for a little more glamour, don’t hesitate to choose a glittery, velvety, or textured tweed option.

Shop Shoes: Express Fiona Kitten-Heel Ankle Boots in Ivory Leather / J.Crew Gwen Flats in Sequin Glitter /  J.Crew Glitter Pumps / Express Textured Asymmetrical Heeled Mules / Express Black Side Slit Crocodile Texture Boots / Express Embossed Block Heel Boots / Express Crocodile Texture Heeled Mules / Express Thick Heel Astor Pumps / Express Closed Toe Wedge Sandals / J.Crew Pointed-Toe Pumps in Colorblock Velvet / J.Crew Sophia Kitten Heels in Leopard / J.Crew Tweed Pumps With Gold Bow


There’s a lot to consider when picking out your wedding guest outfit, and when you need to choose between sleeves or sleeve less, adding a jacket, open vs. closed toes, and styling to match the decadence of the event, it’s easy to get overwhelmed. Regardless of the trends or fashion myths when it comes to wedding guest style, you should always find something that you’re comfortable in and feel amazing wearing. Have fun and happy shopping!

Disclaimer: This post contains affiliate links, meaning that any clicks on these links may result in a small commission to me, at no cost to you. All sponsored posts and affiliate link commissions go towards keeping Lifestyled by Leena up and running! Thanks for supporting my blog!

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