20 Summer-to-Fall Transition Dresses

The Now & Later Dresses

The Now & Later Dresses

Now: Wear with bare shoulders.
Later: Pair with a sleek, fitted blazer.
Printed Drape Back Midi Pencil Dress, $96.74 at ASOS.
The Now & Later Dresses

Now: Show off bare legs and bare arms.
Later: Add in tights and a mid-weight cocoon coat.
Scuba Shift Dress with High Neck in Animals of the Forest Print, $67.71 at ASOS.
The Now & Later Dresses

Now: Rock solo.
Later: Finish off with tights and a slouchy knit.
Baroque Print Skater Dress, $45 at Koshka.
The Now & Later Dresses

Now: Sport with bare legs.
Later: Combine with tights and Chelsea boots.
Blue Belted Shirt Dress, $102 at Pixie Market.
The Now & Later Dresses

Now: As styled, with cool, cut-out booties.
Later: Throw on a set of statement tights.
Cheap Monday Mortal Dress, $80 at Need Supply Co.
The Now & Later Dresses

Now: All alone.
Later: Work in black tights and sleek boots.
A-Line Dress with PVC Detail, $55 at Front Row Shop.
The Now & Later Dresses

Now: Partner with cool boots.
Later: Polish off with black tights and a beige knit.
Black and White Checkered Shift Dress, $51 at Front Row Shop.
The Now & Later Dresses

Now: All alone, with sleeves artfully rolled.
Later: Punctuated by black leggings.
Motel Kye Dress, $72 at Nasty Gal.
The Now & Later Dresses

Now: Anchor with black socks and black boots.
Later: Just swap the socks for tights.
Motel Powelle Dress, $69 at Koshka.
The Now & Later Dresses

Now: As styled, with heeled sandals.
Later: Dress it up even more with black tights and close-toed heels.
In A Flash Dress, $118 at Nasty Gal.
The Now & Later Dresses

Now: Wear all alone.
Later: As styled, with a leather jacket for maximum mod appeal.
Set Stripe Dress, $68 at Nasty Gal.
The Now & Later Dresses

Now: Capped off by normcore sandals like Birkenstocks.
Later: Layered over a white oxford.
Newport Dress, $98 at Need Supply Co.
The Now & Later Dresses

Now: Fashioned with white sneaks like Converse.
Later: Styled with slouchy gray knits.
Only Checked Smock Dress, $50.30 at ASOS.
The Now & Later Dresses

Now: As pictured — worn down and casual.
Later: Dressed up with a long slip and tights.
See The Light Long Lace Shirt, $66 at Pixie Market.
The Now & Later Dresses

Now: As is!
Later: Amplified by black leggings and a bright-colored knit.
Short Sleeve Classic Shirtdress, $245 at Steven Alan.
The Now & Later Dresses

Now: Paired with the sandals of your choice.
Later: Accented by tights and a blazer.
Chambray Shirt Dress, $96 at Topshop.
The Now & Later Dresses

Now: Play up with your favorite sandals or casual sneakers.
Later: Top with a cropped white sweater.
High Neck Jersey Dress, $70 at Topshop.
The Now & Later Dresses

Now: Sport over a short-sleeved tee.
Later: Layer over a killer patterned, button-up shirt.
Pleated Pinny Tunic, $76 at Topshop.
The Now & Later Dresses

Now: Cap off with thick-strap sandals.
Later: Add in your favorite cardigan for the ultimate put-together, lazy look.
Viola Midi Dress, $88 at Need Supply Co.
The Now & Later Dresses

Now: As is!
Later: Combined with tights and your favorite coat.
White and Black Varsity Crochet Dress, $79 at Pixie Market.