Heading to a fall wedding in Woodstock, New York calls for a mix of cozy elegance and outdoor practicality. This collection balances dressy looks with the reality of an autumn outdoor setting. Think rich seasonal tones, flattering silhouettes, and fa...
OK I bought this! I love this one. It has the right amount of elegance, and the price is so good. The only hesitation I had is if the leopard print is too much for a wedding, and it’s final sale. I love it and even if I don’t wear it to the wedding, ...
Sari Maxi Dress in Leopard Print
I love that this is a staple piece you could wear again and again. It’s not too expensive, it’s long sleeve, and it’s a classic black dress that will never go out of style.
Reyna Maxi Dress in Black
I really like this one because it’s plain and simple, but in a good way. It’s long sleeve and a maxi dress, which makes it perfect for a fall wedding. The added waist detail gives it just enough elegance without feeling overdone.
Camryn Maxi Dress in Black
I like how this dress blends a structured, asymmetrical neckline with a back lace-up detail — it gives it a twist (literally) on the typical black maxi. The silhouette feels elevated without being over the top, which is great for a fall outdoor weddi...
ASOS DESIGN high neck plunge maxi dress with blouson sleeves in raspberry | ASOS
I like this one because of the color and the fit. It has that effortless fall vibe, but I’m just not sure if it feels a little too casual for a wedding. If you love it, you can definitely elevate it with the right shoes and accessories.
Malina Maxi Dress in Dark Scales
I love this one — the muted, blurred print gives it softness while the long sleeves keep it seasonally appropriate. The draped detail adds just enough elegance to make it wedding-worthy without feeling over the top.
ASOS DESIGN plisse drape long sleeve maxi dress in pastel blurred print | ASOS
I love this one — that warm brown is perfect for fall. It feels rich and seasonal but still elevated enough for a wedding outside.
Kiara Dress in Dark Espresso
I’m drawn to this one — I love when the fabric has texture or subtle structure that elevates the look. The silhouette looks flattering, and if it has any interesting detail at the waist or neckline, that could make it feel more formal while still bei...
Topshop long sleeve ruffle maxi dress with scarf wrap detail in abstract stripe | ASOS
Love the rich brown for a fall wedding.
ASOS DESIGN soft touch long sleeve drape maxi dress in chocolate | ASOS
I like this one for its clean, sleek lines. The high neckline and sleeveless cut make it modern but the print makes it stand out.
Daska satin maxi dress in dark based floral print | ASOS
I love that this dress comes in both black and brown — that flexibility is gold. It feels classic and streamlined, and the belt detail at the waist adds just enough elegance to elevate the look without going over the top.
Chocolate Slinky Maxi Dress
I’m loving a classic brown maxi — and the asymmetric neckline gives this one just the right bit of character. The warm, rich tone feels perfect for fall, and the unique neckline detail elevates it just enough for a wedding without being over the top.
Deep Chocolate Double Slinky Asymmetric Neckline Maxi Dress
I know this one isn’t for everyone, but hear me out — if the body shape, hair color, and complexion play nicely with these deep fall tones, this dress could look incredible. The rich florals feel very seasonal, and the long sleeves + fitted silhouett...
Dark Chocolate Floral Printed Slinky Long Sleeve Maxi Dress
Oh wow — what a statement dress! The floral burnout adds romantic texture, and the backless detail brings in just the right touch of drama. It feels perfect for a fall wedding in Woodstock or any outdoor, barn-style wedding.
Graceful Arrival Black Floral Burnout Backless Maxi Dress
I really love this one — the blurred mocha mesh gives it a soft, romantic vibe that’s perfect for fall. It has beautiful touches like the plunge neckline, bell sleeves, and tie details that bring subtle elegance without being over the top. It feels l...
Odette Mocha Mesh Maxi Dress
I love this one — the cinnamon / rust tone feels beautifully autumnal and it has a refined, understated elegance. The bolero-style overlay brings interest without going overboard, so it reads polished but not fussy
Myriad Bolero Dress in Cinnamon
This one is a statement pick — the metallic threading, waist cutouts, and open back bring elevated drama. 
If I were using it, I’d lean into that boldness but balance with grounded accessories so it still feels fitting for an outdoor fall wedding.
x REVOLVE Jerri Maxi Dress in Metallic Multi
I love this one — the lace detail paired with a high neck and long sleeves brings a refined, romantic energy. It feels elevated, timeless, and perfectly suited for a fall outdoor wedding. For reference, I’m 5’7”, 130 lbs, and I usually wear a small i...
AFRM Amala Lace High-Neck Long-Sleeve Maxi Dress
I gravitate toward this one — the flowing fabric and ruffle neck detail give it a subtle shine and softness that feel wedding-appropriate. The slip silhouette keeps it sleek and elegant, while the ruffles lend a touch of romantic texture — great for ...
Anora Dress in Black & Gold Foil
This dress has gorgeous drama. The black velvet burnout adds texture and depth, the long sleeves give it fall-friendly coverage, and the silhouette feels sleek yet bold.
Angela Black Velvet Burnout Long Sleeve Maxi Dress
This one is more casual, but depending on the wedding you’re attending, it could really work for a fall formal — especially with the right accessories and styling.
Floral Crinkle Chiffon Milkmaid Maxi Dress
This dress strikes a strong balance — the balloon sleeves and backless detail give it drama and elegance, while the black color and maxi length keep it timeless. It feels wedding-worthy without going over the top.
Prestigious Poise Black Backless Balloon Sleeve Maxi Dress
ZW Collection Midi Dress with Ties (Zara)
I love that this dress also comes in white — though of course you wouldn’t wear that to a wedding. Still, the design itself is such a classic and elegant look, with long sleeves and a tie waist that make it f...
VESTIDO MIDI LAZADAS ZW COLLECTION
Also comes in brown and dark red. This is a comfortable yet still dressy look that’s perfect for a chilly outdoor wedding.
Turtleneck Long Sleeve Drape Ruched Mesh Dress
This dress is an absolute standout. I guarantee if you wear it to a fall wedding or any formal event, no one else will have anything like it. It’s beautifully unique and effortlessly striking.
Mallory Gown in Red Ombre
If you’re looking for a dressier slip option, this is the one. It comes in multiple colors, with and without sequins, but this version truly levels up the look. It’s the perfect elevated slip dress for a fall wedding—just add a chic layer on top.
Anderson Maxi Dress ~ Champagne Shimmery Sequins
This is a nice short dress option… it’s also a full open back!