In the fall of 1972, Halston introduced a dress he called model number 704: an Ultrasuede shirtwaist cut like a man's shirt. The Museum at FIT notes that it follows a man's shirt, with a set-in collar, a back yoke and two-button cuffs. The one big change was the buttons, which start at the breastbone instead of the neckline. The idea is still the same: borrow the shirt, then make it a dress.

 

Halston first saw Ultrasuede on Issey Miyake in Paris in 1971, and his first design in it was a trench coat that absorbed water instead of repelling it. The dress came soon after, with a separate matching wide belt that could be wrapped any way the wearer chose. That is my answer to the belt or no belt question: shirt dresses should work both ways, and the best ones do.

 

Poplin is where I would begin, because crisp cotton is the closest thing to the original shirt. The Emporio Armani in navy has a point collar, three-quarter sleeves and a pleated skirt, and it is the one I would wear to a long lunch with loafers. The Polo Ralph Lauren in white is a mini with a drawstring waist, so in October I would put it over opaque tights and knee boots. The two COS versions are the quiet ones, pale blue with roll-up tab sleeves and a sleeveless white. The 3.1 Phillip Lim in burnt olive has a trapeze shape and pockets, which suits the season better than another white one.

 

Before you commit, button it all the way, sit down and look at the placket across the bust. The Universal Standard Rubicon in black is stretch poplin with a curved hem, and the Lafayette 148 in ink has back pleats for room.

A 1957 issue of Life magazine ran a photo of a typical cotton shirtdress in New York, which shows how far the dress had traveled from Dior's New Look. The informal cotton versions kept the full skirt and collar, and designers like Anne Fogarty became known for them. A stripe is the oldest way to make that cotton interesting, and it is still the easiest.

 

The SUGARLIPS Jordy is bold blue and white in a linen and cotton blend, with a rounded shirttail hem. I would wear it with white sneakers now and with a black blazer over the shoulders in a month. The SHIRTY Sybil is the one I keep coming back to: chocolate brown stripes, long sleeves, French cuffs and a removable sash, a very October color. Alex Mill's Florence is a blue multi stripe with button cuffs, and the Chinti & Parker is an oxford stripe with a self-tie belt. The Zoe and Claire pinstripe adds cap sleeves, a belt and a pleated skirt.

 

Fitting-room test: look at the placket. Stripes should meet cleanly down the front. The Lauren Ralph Lauren midi in orange and white is cut from poplin with a belt. The Polo Ralph Lauren striped tie-waist dress is about 52.5 inches long, which is a real midi, so I would hold it against my knee boots before deciding.

 

What I would skip: the cap-sleeve and short-sleeve stripes as a one-layer outfit after the first cold week. They need a knit or a coat, and then the stripe gets lost. The Julia Jordan in ivory multi stripe I would wear under a cardigan.

Shirt dresses are usually cut without a seam at the waist, which is why they tend to rely on a belt to define it. On the long versions, the belt, or its absence, changes the whole shape, so I would decide that before the color.

 

The Frank & Eileen Rory is full-length linen with a relaxed, airy fit, here in a glitter animal print, and it is the cut I would pick to wear open over jeans and a slim tee, because a straight, soft dress hangs from the shoulder and keeps hanging when it is unbuttoned. The Favorite Daughter Sunday Best in navy has inverted pleats that flare the skirt, so it needs a belt or nothing at all. The Alice + Olivia Lucy is a toile print in stretch poplin with a blade collar and belt, and the Ted Baker in honey ginger has box pleats, pockets and a removable tie belt.

 

The natural linen Manière De Voir Fern has a tie waist and is the plain one I would wear with a long cardigan and ankle boots. The Elan in white has a beaded tie belt. Julia Jordan's navy floral has puff shoulders and button cuffs, and the Reiss Sienna has a neutral print and a self belt.

 

Hem test: stand in the shoes you will actually wear. A maxi should skim the top of a boot or just clear it, and a midi should end at mid calf, never at the widest part. What I would skip: the pleated and belted ones as open layers. A dress built to close will not hang right once it is open.

Fall changes the question from belt or no belt to what goes on your feet. A belted shirt dress with ankle boots, knee boots or loafers looks decided, and it is the quickest way to move a summer dress into October. Leather reads as the season faster than color does.

 

The Celtic & Co. safari midi in chocolate brown has chest pockets and a full button front, and it is the most obvious partner for flat boots. The Polo Ralph Lauren cotton canvas is hunter navy with a tie waist and a flared A-line skirt, and it feels like a barn jacket that became a dress. The Anne Klein is the one that makes me think of Halston: a deep mahogany midi in a soft, suedelike fabric with a spread collar and trench-style belt. Barbour's Sloane in dark navy has a removable self-tie belt, so you can wear it long and straight with a coat.

 

Bella Dahl's navy has chest flap pockets and a drapey tie, and Chelsea28 makes a green-blue floral in modal that I would pick for days with no meetings. Hobbs London's Brigitta has a cinched waist and an A-line skirt, and AllSaints' Yurra has a button front and a tie waist for a slightly harder edge.

 

Test the belt: tie it, sit, then lift your arms. If the dress rides up over the belt, the waist sits too high for you. What I would skip: a thick belt over a bulky coat, because the knot ends up wrapped under the lapels and you lose the shape. Keep what goes under the dress slim, such as a fine turtleneck, so it still reads as a dress.

In December 1972, Vogue photographed Halston among his Halstonettes under the line "A Great Year for Halston", and the Warhol Museum notes that women wanted a dress that could be packed in a suitcase and worn to lunch or dinner. Satin and silk do the same job now, and the shirt shape keeps them from looking fussy.

 

The Halston satin in Garnet Glow has three-quarter sleeves and a tie waist, and it is the fall dress I would pick to wear with black boots and gold hoops. The rag & bone Sonny is fluid army-green silk with a notched collar, flap pockets and a drawstring waist, the most casual here. Donna Karan's berry satin midi has three-quarter sleeves and pockets, and the Rachel Roy Gilian in light silver gray comes with a belt, which softens the gray.

 

For evening, the Max Mara Pelota in ultramarine is matte satin with raglan sleeves and a drawcord waist, and the turquoise piping is on the back skirt panel, so it is a surprise when you walk away. The L'AGENCE Uriah is a black maxi in glossy satin with a belt and shiny hardware. Ted Baker's forest green hammered satin has a twist front.

 

Pairing: boots with a pointed toe, and a wool coat that is longer than the hem. What I would skip: a shiny satin with a shiny belt in the same color, which reads as one flat block.

If I were buying one this week, I would choose the poplin and check the buttons sitting down. Then I would decide on a belt: tied for dinner, off when I want the dress to hang open over jeans.

 

After that I would pick the shoe, a leather boot or a loafer, and add tights if the weather asks. Satin or stripes can come second.

 

Halston started his shirtwaist with buttons at the breastbone in 1972 and a belt you could tie any way you liked. Fifty-four years later I still think that is the whole instruction. I went deeper on a related idea in Prom Dresses: How to Choose One You'll Still Like in Ten Years.