Cool mornings and warm days have descended on my city. That and the massive amounts of pumpkin spice anything being promoted in stores means it is officially fall. I love this time of year and I welcome a return to cozy sweaters and long pants.  A few years ago I asked a few fellow bloggers to share their tips on dressing for fall with vintage and vintage-inspired pieces. Their advice is still relevant but I wanted to add my own ideas that are historically based on real women’s 1940s and 1950s outfits.

Previously, Hotter shoes sponsored the 1940s casual outfit ideas for summer article. Their line of fall/winter shoes is just as fabulous so why not include them again. Being designed and made in the UK,  Hotter knows a thing or two about keeping feet warm and dry. My Whisper boots that I was given to review last year are still my daily winter boot because they are soooo warm and comfortable.

This article is sponsored by Hotter shoes (Thank you!) Links within may be affiliate links meaning at no cost to you I may receive a small commission if you purchase Hotter’s shoes. Use code VINTAGE40 for 40% off and free shipping for new customers.

Hotter “Whisper” Boots are great for winter!


1940s Plaid for Fall

Plaid, especially red tartan plaid, always makes me think of fall fashion in the 1940s. It was equally popular in the 1950s but I like how practical 40s women dressed in plaid. Take this 1940 ad below. On the right, a red plaid long sleeve dress was paired with a matching cap, over the knee knit red socks, and a tan thin belt. The outfit compliments the woman on the left who wears a classic tan double-breasted wool coat. Red plaid + tan definitely go well together and fit perfectly into an autumn landscape.

1940s fall outfit: Red plaid dress, knee high socks, tan trench coat and warm winter boots

Red plaid dress, knee high socks, tan trench coat and warm winter boots

The woman on the right wears tan low heel oxford shoes while the woman on the left wears brown suede heels. Both are good options for light fall weather but I prefer a warm winter boot instead. 1940s winter boots were either lace-up granny boots or fur-lined overboots. Hotter’s Desire boots reminds me ’40s overboots with the faux fur lining, over the ankle height and thick weatherproof sole. It is a nice blend of vintage and modern footwear.

Desire boot with faux fur lining

Desire boot with faux fur lining

1940s Fall Pants Outfit

Despite my love of plaid I rarely wear dresses in the fall. I am more comfortable in casual pants and simple tops.  So did women in the 1940s. High waisted and wide leg pants in all sorts of fall-friendly prints and colors filled page after page of shopping catalogs. Most pants were paired with a long sleeve button-down blouse. The look was intended to emulate menswear but with feminine fabrics and shaping. I love the striped blouses in the ad below and the herringbone print bow blouse paired with green wide leg pants from Unique Vintage is spot on.

Instead of a long overcoat, I thought a short belted jacket in the 40s style is a better pairing for a not-too-cold-yet fall outfit. Layer it over a few pairs of wige leg, high wiast pants and a handful of long sleeve blouses and you will have enough to craft an entire season of casual 40s outfits.

1940s high waisted pants, bow blouse, belted jacket, and casual Dorset loafer shoes

1940s high waisted pants, bow blouse, belted jacket, and casual Dorset loafer shoes

The best 1940s shoes for a casual outfit are slip-on loafers. They were extremely common in the 1940s yet they haven’t been picked by vintage enthusiasts as much I would like to see. Hotter’s Dorset loafer is a near perfect 40s style loafer. I love the new navy/tan two-tone combination but a solid black would go with everything. For something a bit more trendy why not try the Dorset loafer in plum? Grey trousers, cream blouse, and plum loafers sound like a delightful combination that can transition into spring as well.

Vintage style black and brown two tone loafer by Hotter

Dorset loafer in dark navy and tan

Here is another outfit from my summer article pairing the corset loafers in blue/cream (now sold out) with jeans and a plaid shirt. This works equally well for fall with a nice flannel weight button down shirt.

1940s casual jeans outfit

1940s casual jeans outfit

1950s Jumper or Pinafore Dresses

Moving into the 1950s I am drawn to the jumper dress or pinafore dress in the UK. I like them for fall because they can be layered over a long sleeve blouse or knit shirt for warmth. If you have a sleeveless summer dress that isn’t too summery- they can do the same job. Most jumpers/pinafores out right now are made of wool plaid, solid cotton or corduroy. The later is harder to find but so nice when you do. Talk about a warm fall fabric!


In the vintage pic above the plaid jumper was paired with Hotter’s Jewel flats which have an adorable bow on the top and a slightly raised wedge sole. Brown goes with everything which is why I choose it. So do brown boots. The eShakti picture on the right shows another fab pairing of a jumper dress, knit top and knee high boots. Hotter has a pair of Belle brown boots that would also be great for another vintage meets modern look.


1950s Festive Fall Outfit

What I love about 50s fashion is all of the novelty prints. Border print skirts and dresses are some of my favorite clothes to collect. I tend to pick up new skirts for each season or holiday. For fall I found an adorable autumn print skirt on Amazon and paired it with a mustard yellow 50s button down blouse, wide black belt, and Hotter’s Donna heels in jet black. Isn’t it perfect? I could wear this to the pumpkin patch with my kids or to a fall harvest swing dance

1950s fall Autumn outfit - Festive Autumn skirt, mustard blouse, black bow belt, with Hotter's Donner Heels in black

Festive Autumn skirt, mustard blouse, black bow belt, and Hotter’s Donna Heels in black

If you already own a pair of  Donna heels you know how comfortable they are. I LOVE my pair in blue suede but did you know they updated the Donna heel this year? It now was a pointier toe instead of the heavier square toe it has had the last few years. I love the boxier toe for ’40s outfit but this new toe shape is better for the 1950s.  I can’t wait to get a new pair in all the colors especially black and red.


What outfits are you wearing for fall this year? Share in the comments.



Subscribe to Our Newsletter for Discounts, Promotions & Latest News


Please enter your comment!
Please enter your name here

7 + 4 =