In 1954, a New Haven native named Richard Liebeskind opened a shop on Chapel Street and hung a name over the door that belonged to nobody. Ann Taylor was the best-selling dress in his father's womenswear showroom, and he borrowed it. The "Ann" was a popular name around New England, and "Taylor" suggested tailored, well-fitting clothes. A dress gave the brand its name, which is why Ann Taylor dresses feel like the center of the whole house. If you want to keep going, Country Wedding Guest Dresses: The Prairie Dress Goes to the Barn is the one I would read next.

 

The brand grew up dressing women for work, with classic tailored styles, crisp button-downs and sharp suits. That is the point of view I keep coming back to. Nothing here is trying to be a costume. The clothes are made to get a person through a full day of meetings and still look composed at the dinner after.

 

Which brings me to the sheath. The Seamed V-Neck Sheath Dress in Bi-Stretch in black is the one I would start with, cut close and simple with a shell of 66% polyester, 28% rayon and 6% spandex. The Short Sleeve Sheath Dress in Bi-Stretch comes in toasted oat, a softer neutral for someone tired of black. For an October office, I would put the Belted Crew Neck Sheath in Seasonless Stretch, in deep navy, under a camel coat. The Pinstripe Crew Neck Sheath in a dark neutral nods to the boardroom without a blazer on top.

 

In my fashion dreams, she is crossing a lobby at 8:55 in the Square Neck Sheath in core black, short sleeves with slit cuffs, a pair of loafers, a tote that fits a laptop. Practical tip: sit down in a sheath before you decide. Hips, shoulders and a long meeting should all agree with it.

The brand says many of its styles are machine washable, and that is worth checking on the tag of any wrap before you fall for it. Wraps get worn often, so a dress that asks for no fuss gets reached for more. That is a very Ann Taylor way of thinking, built around the working week.

 

The collared wraps are the ones I would look at first. The Collared Wrap Midi Dress in harbor side blue has long sleeves with button and loop closures at the cuff, a neat detail that keeps the sleeve from riding up under a coat. The Geo Print Collared Wrap Dress in night sky is shorter and has a point collar, which reads dressed up even with flat boots. The Collared Wrap Shirtdress in amber noir goes a more autumnal way, with front button closures.

 

For warmer rooms, the linen blend wraps are lighter. The Floral Midi Wrap Dress in rhododendron and the Petite Linen Blend V-Neck Wrap Dress in black share a shell of 55% linen and 45% viscose with a cotton lining. The Polka Dot Linen Blend Sheath in white sits in the same family, and the Weekend Striped Tie Waist Midi in night sky is the casual one, cotton blend with a tied waist.

 

The test is simple. Tie or wrap the dress, sit down, reach for something on a high shelf, and see whether the front stays closed. A wrap should move with you.

 

What I would skip: the shirred floral flare in blue if you want something to wear under a blazer. It is made to be seen on its own.

Midi length is where the workwear mindset and the weekend meet, and most of the Ann Taylor midi dresses are built on a shirtdress. Almost every one has a collar, a belt or a hidden placket, so they look pulled together fast. I would call that the brand's habit.

 

The Belted Midi Shirtdress in tinto red is my favorite for October, a split neck and long sleeves with button cuffs, in a color that looks good against bare trees. The Paisley Belted Midi Shirtdress in purest plum has elasticized cuffs, which makes layering a cardigan easy. The Floral Midi Shirtdress in black is the quiet version, and the Horsebit Print Midi Shirtdress in sand shell is a softer, lighter option that works with a tan trench.

 

Two of these step away from the shirt shape. The Plaid Cowl Neck Midi Dress in French mocha is sleeveless, so I would put a thin knit under it and a pair of knee boots below. The Paisley Puff Sleeve Midi Dress in French mocha has elasticized cuffs on the short sleeve, and for me it is a dinner dress. The Pleated Polo Midi in winter white and the Belted Lace Midi Shirtdress in night sky, with its hidden-button placket, round it out.

 

Practical test: stand with your arms crossed and look at the belt line. If the belt wants to ride up, the dress is the wrong length for your torso.

 

What I would skip: winter white if you are carrying a bag with dark dye. It will pick it up.

Sweater dresses are where Ann Taylor lets its tailoring slip into something soft, and I like that they still carry the brand's habit of collars and belts. Most are a blend of polyester, viscose and nylon, so they hold their shape better than a pure wool one would. Check the fiber list on the page before you choose.

 

The Ribbed Turtleneck Sweater Dress in soft mink melange is the plain one, and I would wear it with flat boots and a long coat. The Belted Sweater Dress in cashew crunch has a split neck and a belt, so it can lean office or weekend. The Tie Waist Midi Sweater Dress in dusted orchid has a ribbed crew neck, cuffs and hem, and the soft color keeps it from feeling heavy.

 

Then the polos. The Weekend Cable Polo Midi in night sky and the Pointelle Polo Midi Sweater Dress in ocean oasis both put a point collar on a knit, which is a nice way to dress up a cold desk. The Collared Sweater Dress in white and the Weekend Striped Sweater Shift in camel multi are shorter, and I would add tights to either one.

 

For fitting, raise your arms and see whether the hem moves. Then sit, and look at the knee. A knit that rides up while sitting will do it all day.

 

What I would skip: the Animal Print Mini Sweater Dress with a heavy coat. A mock neck with a thick collar is too much stacked together.

Occasion dressing has its own history here. In 2010 a cream floral lace sheath, worn by a model in the store windows, sold out in a matter of days. That tells me a sheath with some drama is what people want when they have somewhere to be.

 

The Studio Collection pair is the dressiest here. The Boatneck Midi Dress in Genuine Silk, in dark fuchsia bloom, and the Paisley Midi Dress in Genuine Silk, in night sky, are both 100% silk with a polyester lining. The second runs to maxi length, which I would pick for a winter wedding as a guest. Silk wants a cool, dry hand, so check the care tag before you buy. I went deeper on a related idea in Casual Wedding Guest Dresses: Rose Pecchia's Detroit Lunch-Hour Dress.

 

The slip dresses are easier. The Lace Trim Satin Midi Slip in purest plum is a night-out dress, and the Belted Vest Slip Dress in deep forest pine is a clever one: it looks like a vest with a skirt attached. The Floral Corset Midi in cheerful blue is the one for a garden party, and the Lace Flutter Sleeve Midi in olive sprig has short sleeves that cover the shoulder. The Floral Cowl Neck Maxi in opal blush is a gentler option, and The Flare Dress in Fluid Crepe in pure sapphire is the easiest of all.

 

For a wedding, I would skip anything that reads white. The ones above are all in color, which is the polite choice.

 

What I would skip: lace over a bright slip if the evening is very warm. Pick the crepe instead.

I would start where the brand started, with the dress that was named after a dress. If there is a job interview, the black Seamed V-Neck Sheath in Bi-Stretch. If there is a long Friday, the Belted Midi Shirtdress in tinto red. If there is a wedding, the Studio Collection silk.

 

Then I would check the sleeves, the belt and the length in that order, because that is where a work dress succeeds or fails. Pick one that you can sit down in.

 

Somewhere in a New Haven showroom there was a dress called Ann Taylor, and a brand grew out of it. I like thinking that every dress here is the next one in a very long line.