30 of Fall's Best Dresses

There's something about a beautiful fall dress that makes even the simplest occasion feel special. From cozy sweater dresses and polished corduroy for everyday to romantic florals, rich velvets, and beautiful silks for autumn weddings and evenings out, this month's edit is full of pieces I truly love. I'm especially drawn to the rich colors and textures of the season: chocolate brown, burgundy, olive, suede, and jacquard. I've also included a few longtime favorites from my own closet, because I firmly believe that when you find a dress you absolutely adore, it's worth investing in and wearing for years to come. Here are my favorite dresses for October, whether you're headed to school drop-off, a cozy weekend lunch, or something a little more special.

I don't usually feature old pieces in my blog posts. However, the Oscar de la Renta dress above is one of my favorite dresses that I reach for all the time, and I think it's worth sharing simply because I want to encourage you: when you buy something that's marvelous and you truly love, you can wear it year after year. I've worn it to September weddings, my grandmother's 90th birthday, and special dinners throughout the years. A few other dresses that have a similar feel include this, this, and this (on sale). I love pairing fall florals with an equestrian-inspired bag (the hardware is so right for autumn) and these brown suede stiletto boots, a splurge I wear constantly, but these are almost identical and really quite good.
Rich burgundy florals make this tiered dress perfect for the season's best events. (Gorgeous with a T-strap heel like this!)
The scarf-print border on this navy shirt dress looks so pretty with boots or pointed-toe flats.
For holiday parties and fall weddings, I love this romantic brown jacquard midi dress with the most dramatic sleeves.
If you want one sweater dress for the whole season, this wrap midi in dark brown is a wonderful merino-cashmere blend, with a tie waist that looks like a knotted sweater. (I have last year's color, seen here.) It would look fab with these leopard slingbacks! It also comes in a gorgeous red, and Sezane's ribbed red knit dress gives a similar cozy look for $220. Knee-high boots for work, heels for dinner.
A smart denim shirtdress works for almost any fall occasion, and the styling possibilities are endless.
Velvet season is here, and this jade V-neck dress with draped shoulders is absolutely stunning. (I wore it here!) It's my pick for an autumn wedding or holiday dinner, styled with strappy gold heels and a beaded bag.
Corduroy dresses are my favorite fall shortcut, and this merlot corduroy dress and best-selling olive mini dress both look fab with a paisley scarf around your neck and loafers for coffee runs now, then tights and boots once it gets chilly.
Two sweater dresses for two moods: this speckled oatmeal merino midi reminds me of The Row and is so polished with tall brown boots. This charcoal wool rollneck mini dress is easy with opaque tights and loafers for school drop-off.
Emporio Sirenuse has the most incredible embroidery, and this dress is a year-round stunner.
This leopard silk-blend dress has a pretty tie neck that works at the office and at dinner. I love how they styled it with this belt (20% off with StacieF20).
Suede and leather dresses feel so luxe this season. Ann Mashburn's khaki suede dress has a tie waist and easy shirtdress shape, and Sezane's leather mini is so chic layered over a blouse. I'd finish both with my leopard ballet flats, which are incredibly comfortable and work so well for grounding suede pieces.
My cream ribbed knit midi dress is such a versatile fall piece (I've worn it a few times already, seen here). Style it now with suede boots and a statement necklace for school drop-off or lunch, then later with sandals for spring.
A shimmery black maxi dress with a twist front and deep V is made for evenings out and is at the top of my wishlist!
Hill House Home's metallic floral top and matching skirt are made to go together, and the tie shoulders are such a pretty detail. Style them as a set for holiday parties with strappy heels, or split them up: the top with black trousers, the skirt with a cashmere sweater.
Dupioni silk gives this paisley shirt dress (15% off with STACIE15) a gorgeous sheen, and the belted waist and full midi skirt are so flattering. It's an easy pick for a fall brunch or shower now, then later with sandals in spring.
The waterfall seams on this metallic brocade gown cascade into a kick-pleat hem, and the rust and cream floral is so striking. The square neck and sleeveless cut feel modern with black pumps for an evening wedding or gala.
This black wool off-the-shoulder midi dress (also in brown) is the kind of piece you'll keep for years. The fitted bodice and swingy skirt look polished with heels for dinner now, then with tall boots and a long coat as the weather turns colder.
I love the vibrant orchid shade of this silk dress with its dramatic ruffle cascading down the front. It's a splurge, but it can go from a fall wedding with heels to a special dinner with brown leather boots.
This merlot ikat silk dress has a sweet bow at the waist and flowing sleeves. It would look stunning with strappy heels now and boots as temperatures start to drop.
Tory Burch always has at least one standout silk dress each season, and this black-and-white stunner has an unexpected print and beautiful movement.
Collared and cozy, this gray sweater dress (only $100!) is made for school drop-off with sneakers or ballet flats.