The drop waist dress is one of those shapes that keeps coming back. The waistline sits low on the hip, and the skirt flares or gathers from there, so it skims the body instead of cinching it. I went deeper on a related idea in Drop waist skirt: The Fall Line Is Moving South.

 

It started as a summer trend, but it works even better in fall. Add tights, knee high boots and a cardigan over the shoulders and the shape suddenly looks cozy and a little vintage, in a twenties way.

 

Below are the drop waist dresses I would wear right now, split into sleeves, black, and warm fall colors.

Sleeves make a drop waist dress feel like fall without any extra layers. The brown dress with short sleeves and a curved hip seam is the one I would buy first, because it looks great with tights and loafers.

 

The black version with a ruched bodice and short puff sleeves is a perfect desk to dinner dress. The navy cotton dress with flutter sleeves and the navy poplin shirt dress both have that easy, swingy shape. The ivory long sleeve dress is the lightest option and pairs with a brown belt and boots. The long sleeve sheer maxi in cedar is best over a slip with a leather jacket.

 

My fitting room test: sit down. The seam should land on the top of your hip, not your thigh. What I would skip: very stiff fabric that makes the skirt stand away from your body.

A black drop waist dress is the most useful version. It works with black tights and boots for daytime and with heels and a coat at night.

 

The long sleeveless black dress with a fitted top and full skirt is the evening option. The smocked bodice dress is easier to wear and more forgiving. The ankle length dress with a gathered skirt looks great with a chunky knit. The strapless black dress is for layering over a fine turtleneck. For a change from plain black, the dress with a black top and cream skirt, and the black midi with a cream floral print, both keep the shape but add some contrast.

 

What I check: the bodice should be snug enough that the low seam stays put. What I would skip: thin jersey that clings at the hip.

Brown, plum and deep red make the drop waist dress feel seasonal. The nutshell brown mock neck dress is simple and pairs with black boots. The plum gathered maxi has a twist at the hip that is very flattering.

 

The espresso tiered dress feels romantic, and the brown plaid drop waist dress is the most fall of them all. The coffee off the shoulder maxi is a nice option for dinners, and the deep red dress is a statement for a party.

 

My test: check the length with your boots on. A midi dress that hits just below the knee shows a sliver of tights, which looks intentional. What I would skip: bright summer prints, which fight with fall coats.

Pick one with sleeves or one in black first. Add opaque tights, a knee high boot and a cardigan tied over your shoulders.

 

Keep the top of the outfit simple so the low waist does the work. A small bag and a slim belt are enough.

 

To round out the look, see Basque Waist Wedding Guest Dresses and Tom Ford Bags and Dresses.