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 [1] 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 favourite picks that you can shop, too. I found everything from cute minis you can pair with jackets and over-the-knee boots [2] 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.
Chelsea28 Floral Satin Midi Dress
The high neckline on this Chelsea28 Floral Satin Midi Dress [4] ($149) is so pretty.
cupcakes and cashmere Frankie Dress
You can wear this cupcakes and cashmere Frankie Dress [5] ($118) with over-the-knee boots when it gets cold.
Faithful the Brand Farah Midi Dress
Whether you style this Faithful the Brand Farah Midi Dress [6] ($189) with sandals or sneakers, it will always look good.
H&M Pleated Wrap Dress
Pair this H&M Pleated Wrap Dress [7] ($70) with a moto jacket and boots in the Fall.
Keepsake Lovesick Mini Dress
We adore the print on this Keepsake Lovesick Mini Dress [8] ($185).
Reformation Vollare Dress
Add a denim jacket and fun ankle boots to this Reformation Vollare Dress [9] ($198).
CeCe Botanical Charm Cascading Ruffle Sleeveless Dress
Wear this CeCe Botanical Charm Cascading Ruffle Sleeveless Dress [10] ($139) to your next event.
H&M Pleated Long Dress
The shade of this H&M Pleated Long Dress [11] ($70) is so pretty.
Rachel Parcell Button Down Midi Dress
Dress up this Rachel Parcell Button Down Midi Dress [12] ($99) with PVC heels.
Reformation Carina Dress
You can wear this versatile Reformation Carina Dress [13] ($218) year round.
Reformation Dalie Dress
There's no better time to rock a little snake print than in Fall, so snag this Reformation Dalie Dress [14] ($248).
ENGLISH FACTORY Swiss Dot Smocked Maxi Dress
No doubt you'll turn heads in this stunning ENGLISH FACTORY Swiss Dot Smocked Maxi Dress [15] ($115).
Reformation Hayden Dress
Wear this Reformation Hayden Dress [16] ($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 [17] ($95) is from.
GANNI Printed Georgette Dress
This GANNI Printed Georgette Dress [18] ($160) belongs with a pair of cute Western-style boots.
The Fifth Label Current Long Sleeve Midi Dress
You can wear this The Fifth Label Current Long Sleeve Midi Dress [19] ($120) to the office and beyond.
Rahi Garden Cassie Dress
Add some colour to your wardrobe, no matter the season, with this Rahi Garden Cassie Dress [20] ($172).
H&M Dress with Smocking
You'll wear this H&M Dress with Smocking [21] ($25) again and again.
H&M V-Neck Dress
You can style this H&M V-Neck Dress [22] ($35) for every season.
Loft Dotted Pleated Wrap Midi Dress
Wear this Loft Dotted Pleated Wrap Midi Dress [23] ($129) with comfy heels and a leather jacket.
Rare Feelings Maxi Dress
Throw on a sweater with this stunning Rare Feelings Maxi Dress [24] ($148).
Reformation Lacey Dress
You can wear this printed Reformation Lacey Dress [25] ($248) with flats and a cardigan.
Row A Shirred Bustier Bodice Sundress
This Row A Shirred Bustier Bodice Sundress [26] ($49) also comes in a red printed choice.
Gal Meets Glam Collection Alma Two-Colour Gingham Halter Neck Dress
The mix of prints on this Gal Meets Glam Collection Alma Two-Colour Gingham Halter Neck Dress [27] ($148) is so pretty.
POPSUGAR at Kohl's Printed Midi Dress
Take this POPSUGAR at Kohl's Printed Midi Dress [28] ($48, originally $60) from the office to date night.
Endless Summer Frances Midi Dress
This Endless Summer Frances Midi Dress [29] ($98) is so versatile, you'll own it forever.
Leith Midi Wrap Dress
This Leith Midi Wrap Dress [30] ($59) comes in so many cute patterns and colours.
Loft Garden Split Neck Pocket Dress
The colours on this Loft Garden Split Neck Pocket Dress [31] ($90) are so eye-catching.
Feeling Groovy Maxi Dress
Turn heads in this Feeling Groovy Maxi Dress [32] ($168).
Gal Meets Glam Collection Peyton Belted Linen Blend Sundress
The print on this Gal Meets Glam Collection Peyton Belted Linen Blend Sundress [33] ($198) is so cute.