That's a cool picture Chris found. I was born in the mid-50s and vaguely remember some of the details of being brought there as a kid, so let me fill in what I can from memory.
Sears had no standalone retail stores in Halifax-Dartmouth until the early/mid-80s. The Dartmouth Penhorn store opened in '82, and according to the Sears website "The end of the 25-mile agreement some years earlier paved the way for Sears to open a store in Halifax. Ironically, the new Sears store opened in the former Simpsons location." That occurred in '84. Prior to that time, Sears products were available by ordering them from the Sears catalog. I don't think that Sears brands such as Kenmore were available in a normal retail setting in Halifax at Simpsons-Sears, though I stand to be corrected on that. I believe that you could look at floor models in the catalog shopping center and buy returned units in the clearance center (more on that later). My memory is that S-S had their own unique house brand, but I can't remember the name. Later on, after the split in the mid-80s, the Bay developed their own Beaumark house brand of appliances. The history of Simpons, Simpsons-Sears, Sears, and the Bay is very convoluted, as a Wiki search will reveal.
In Halifax, the original Simpsons store opened on Chebucto Lane sometime around 1930. It was in the suburbs at the time, but was serviced by tramcar and later by NSL&P trolleys. There was a circle to allow the trolleys to reverse course in front of the main entrance, which was nicely landscaped and had the feel of a small park/garden. This is roughly where a loading dock now is situated. I recall being in the Simpsons store not long before they relocated to the new structure that currently houses The Bay and the area immediately inside those doors was the mens wear department, with much old wood millwork and polished trim - very old-school in design. Towards the center of that floor was a candy/baked goods dept which I loved as a kid, with bulk candy displayed in glassed-in showcases that a clerk would scoop out and sell by weight in little white paper sacks with blue Simpsons logos on them. I believe ladies wear was at the opposite end of that floor, but I may be wrong on that point. I never paid much attention to that when I was a kid.
In the 1960s the new structure pictured was built behind the old store and attached to it. This was always very confusing to me because there were escalators that took you upstairs from the old store to the new, which was still Simpsons, but there were also elevators - at least 2 different sets - that took you upstairs as well, and depending upon which one you took, you could either go to the new retail sales floors in the new building, or to the clearance center/catalog shopping center, which was Simpsons-Sears, not Simpsons. This remained, as near as I can recall, in the old original building.
(NOTE: I actually have 2 conflicting memories on this point. One is that the elevators took you directly to the catalog sales area. The other is that an elevator took you to a level where you exited into a display area of appliances and home improvement goods, which was adjacent to a restaurant - the Arcadian Room, I believe, a Simpsons name - and you continued past it down a long corridor before arriving at the catalog center. Perhaps this was the result of renovations during that time).
The new Simpsons building contained a floor that had a large record, music and TV dept, furniture, appliances, cosmetics, and god-knows what else. I seem to recall one area being designated as "The Room", with upscale women's fashions. But my memory of it is fuzzier than that of the old main floor for some reason. When it first opened it was standalone as the West End Mall had not yet been built. At the far end (towards where Sobeys is now) were administrative offices, which had their own exterior entrance. I recall that the entrance from outside on that level was also rather nice, with a good-sized airlock lobby with expensive-looking double glass doors. This was a popular spot to wait for your bus. The exterior on that level had a neat design that you can see in the picture, with a white quartz pebble-finished precast the entire length of the building. It's a shame that went away - it was cool mid-century architecture.
The catalog and clearance floor in the original building was very different, an industrial sort of setting with few amenities or architectural features. You got off the elevator (or exited the corridor, whatever memory is accurate) and were near a catalog order area, where you would be served at a large counter by clerks who would fill out order forms for items selected from the catalog. These were sent to the order pickers using a pneumatic tube system, whose noise and drama impressed me very much as a kid. In the mid-1960s there was a soda machine there which I always pestered my parents to let me use since it was so cool. It was the type that took your money, dropped a paper cup into a recptacle behind a transparent door, which then filled with the flavor of soda you selected using pushbuttons. I always got an orange soda that was very fizzy and not very good, as I recall. The things you remember...
There was (I think) a 30 or 60-minute order turnaround time where the in-stock items you ordered would be brought down from the warehouse areas and placed in large pigeonholed shelving units behind long counters that ran the length of a large gallery area. Large items too big for shelving had a separate area. These shelves were coded by letter and number which the clerk taking your order would write on your claim check which was given to you when taking your order, along with the time you could pick up the items. I remember these were preprinted with the word "RUSH" in big red letters along with the sentence "Customer waiting in catalog center" or something close to that. At the appointed time you would present yourself at the appropriate spot and give another clerk your claim check, and your merchandise would be taken from the shelves and given to you for inspection and either purchase or rejection. Sometimes the exact item was not in stock and they would substitute something in a different color or style, which always made for a bit of an adventure and sometimes, interesting discussions.
At the end of this gallery area was what my parents called the bargain center. This was a popular destination to visit while waiting for your catalog order to be sent down. This area held items that were returned for credit, were slightly damaged or otherwise imperfect, or (allegedly, according to someone I knew who worked there) were ordered but not purchased. According to this person it was possible to get items at huge discounts if you knew how to work the system of ordering and returns. I do recall that some items seemed very cheap compared to the prices in the catalog. This was not all that different from the current-day clearance center except my memory of it was that it was smaller, darker, and much more confused in how it was merchandised.
Simpsons (as opposed to Simpsons-Sears) was a somewhat upscale, traditional department store in those days. It carried prestige brands and was aimed at a customer slightly more upmarket than what The Bay tries to capture today. Simpsons-Sears was really a separate company that shared facilities here with Simpsons but carried its own line of merchandise that was available here via catalog order (I understand in other markets they had their own retail stores which offered those S-S products in a regular retail setting), and which was more or less similar to what Sears still offers today. It competed back then with the Eatons catalog in that style of retail.
There's my memory dump of that site's history.