Best Transitional Dresses 2019
30 Stunning Dresses You Can Buy Now and Wear Well Into November

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August is that awkward month when Fall clothes start hitting the racks and I get excited to start dressing for cooler weather, but it's still scorching hot outside. The best way to satisfy my seasonal cravings without jumping the gun is by investing in transitional pieces I can wear for more than one season. Right now, flattering dresses are at the top of my wish list, and I'm looking to treat myself to a few finds that I can wear now and well into Fall. I went on the hunt for versatile picks that are easy to style more than just one way.
Ahead, I gathered a list of my 30 favorite picks that you can shop, too. I found everything from cute minis you can pair with jackets and over-the-knee boots and midis you can layer with sweaters when the weather starts to change. Plus, prices start at just $25, so maybe you can get two. Keep reading to check them out.
Rare Feelings Maxi Dress
POPSUGAR at Kohl's Printed Midi Dress
Take this POPSUGAR at Kohl's Printed Midi Dress ($48, originally $60) from the office to date night.
Endless Summer Frances Midi Dress
This Endless Summer Frances Midi Dress ($98) is so versatile, you'll own it forever.
H&M Dress with Smocking
Gal Meets Glam Collection Alma Two-Color Gingham Halter Neck Dress
The mix of prints on this Gal Meets Glam Collection Alma Two-Color Gingham Halter Neck Dress ($148) is so pretty.
Leith Midi Wrap Dress
This Leith Midi Wrap Dress ($59) comes in so many cute patterns and colors.
H&M V-Neck Dress
Gal Meets Glam Collection Peyton Belted Linen Blend Sundress
The print on this Gal Meets Glam Collection Peyton Belted Linen Blend Sundress ($198) is so cute.
Feeling Groovy Maxi Dress
Row A Shirred Bustier Bodice Sundress
This Row A Shirred Bustier Bodice Sundress ($49) also comes in a red printed choice.
Chelsea28 Floral Satin Midi Dress
The high neckline on this Chelsea28 Floral Satin Midi Dress ($149) is so pretty.
Loft Garden Split Neck Pocket Dress
The colors on this Loft Garden Split Neck Pocket Dress ($90) are so eye-catching.
Rachel Parcell Button Down Midi Dress
Dress up this Rachel Parcell Button Down Midi Dress ($99) with PVC heels.
CeCe Botanical Charm Cascading Ruffle Sleeveless Dress
Wear this CeCe Botanical Charm Cascading Ruffle Sleeveless Dress ($139) to your next event.
Loft Dotted Pleated Wrap Midi Dress
Wear this Loft Dotted Pleated Wrap Midi Dress ($129) with comfy heels and a leather jacket.
H&M Pleated Wrap Dress
Pair this H&M Pleated Wrap Dress ($70) with a moto jacket and boots in the Fall.
Reformation Hayden Dress
Wear this Reformation Hayden Dress ($218) with sandals in Summer or a coat and sneakers in cold weather.
Topshop Bardot Spot Print Asymmetrical Off the Shoulder Dress
Everyone will want to know where this pretty Topshop Bardot Spot Print Asymmetrical Off the Shoulder Dress ($95) is from.
Faithful the Brand Farah Midi Dress
Whether you style this Faithful the Brand Farah Midi Dress ($189) with sandals or sneakers, it will always look good.
H&M Pleated Long Dress
The Fifth Label Current Long Sleeve Midi Dress
You can wear this The Fifth Label Current Long Sleeve Midi Dress ($120) to the office and beyond.
Reformation Carina Dress
Reformation Dalie Dress
There's no better time to rock a little snake print than in Fall, so snag this Reformation Dalie Dress ($248).
cupcakes and cashmere Frankie Dress
You can wear this cupcakes and cashmere Frankie Dress ($118) with over-the-knee boots when it gets cold.
Reformation Vollare Dress
Add a denim jacket and fun ankle boots to this Reformation Vollare Dress ($198).
ENGLISH FACTORY Swiss Dot Smocked Maxi Dress
No doubt you'll turn heads in this stunning ENGLISH FACTORY Swiss Dot Smocked Maxi Dress ($115).
Keepsake Lovesick Mini Dress
Reformation Lacey Dress
You can wear this printed Reformation Lacey Dress ($248) with flats and a cardigan.
GANNI Printed Georgette Dress
This GANNI Printed Georgette Dress ($160) belongs with a pair of cute Western-style boots.
Rahi Garden Cassie Dress
Add some color to your wardrobe, no matter the season, with this Rahi Garden Cassie Dress ($172).