1940s Casual Outfits: Summer Clothes & Shoes

I love it when readers ask me for help with vintage outfits. One recent request was ideas for 1940s casual outfits. I have seen this topic come up a few times in some groups I follow as well. “Casual” and “vintage” usually do not belong in the same sentence. What was casual or informal in the 1940s would look very dressy to us today in the times of athleisure and loungewear. What you might think of as casual clothing in the 1940s was women’s workwear or summer clothes. Work clothes were heavy jeans, overalls, or trousers with flannel shirts and loose jackets. Summer clothes are a bit more fun with high waisted shorts, wedge sandals, and blouses.

This week, I also received a pair of Hotter Hallie shoes in red. I have reviewed Hotter’s VERY comfortable shoes before (Vivienne T Straps, Dorset loafers,Donna heels). It is one of the few brands I can recommend for both vintage style and comfort. I paired the following 1940s casual outfits with Hotter’s shoes to give you ideas on how to coordinate casual vintage clothes with vintage style shoes.

** 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. **

1940s Casual Outfit: Shorts & T-Shirts

1940s T-shirts called Polo shirts

Who doesn’t love a soft comfortable T-shirt and a pair of shorts in summer? It is the ultimate simple summer outfit you can wear. Thankfully, T-shirts existed in the 1940s, as did high waisted shorts. 1940s style T-shirts were knitted cotton fitted shirts with a ribbed ringer crew neckline. They were not called T-shirts, but polo shirts instead. Necklines often contrasted with the shirt body, especially with striped shirts that came in red and white or blue and white stripes. Solid color or thin stripe shirts in red, blue, grey, yellow, white and beige were also casual styles. Long sleeve T-shirts with the sleeves pushed up were another option. Shop shirts.

T-shirts paired well with high waisted shorts and trousers. They could be worn tucked in or untucked. For summer, I like to pair them with shorts in navy blue cotton, chambray denim, black, or white with at least a 5-inch inseam. Sailor buttons on the sides are very vintage, but other shorts styles like flared, Bermuda, or culotte, lengths look equally ’40s. Shop shorts.

The final piece to this simple outfit is a pair of shoes. White wedge or peep toe platform shoes are what most 1940s models wore. Black, blue, or any color shoe that matched the shirt will be easier to find than white. In the collage below, I paired a red and white striped shirt with blue shorts and red Hallie shoes. The wedge on the Hallie shoe is only 1.5 inches, which makes them very easy to walk in and much more casual than most sky-high wedges or espadrilles.

1940s causal outfit with shorts and red wedges

1940s Casual Outfit: Pants

When the weather is not too hot or you just want to wear pants, you can substitute the shorts in the above look and have another simple summer outfit. Solid color or striped T-shirts can be worn with high waisted, wide leg pants in a full range of colors. Blue or beige are my favorites because they go with everything. An alternative to a T-shirt is to wear a cotton blouse. Button-down blouses tend to not be casual enough for most women, but if you choose a colorful small print, like vertical stripes or polka dots, they will read casual, cute, and easy going. In winter, try a long sleeve plaid shirt like a men’s flannel shirt instead. Shop tops.

1940s casual outfits with pants or trousers

Wedges or heels with casual pants generally do not go well. Most women in the 1940s wore flats in the form of penny loafers or modest slip on-shoes. Low heel canvas slingback shoes and saddle shoes were other options. Personally, I love a good pair loafers. I slip them on in the morning and wear them around the house all day. I think they look best without socks, but in winter, a dark colored sock is a warmer option. Most ’40s loafers were brown or black, but some came in two-tone blue and white or brown and white combinations just like the Hotter Dorset loafers. They ran a tad bit narrow on my almost wide foot, so next time I will order them in wide.

1947 loafers side by side with the Hotter loafers (original color is brown but I edited it to show what a blue would look like)

1940s Casual Outfit: Jeans

I live in jeans, just jeans, all day, every day. If you live in your jeans, too, there is a quick and easy way to make a ’40s outfit with them. Pair them with a button-down shirt, leather belt, and loafers. Most women who wore jeans in the 1940s were either working (at home or on a job), riding horses, or were teenagers. Teens borrowed Dad’s or Brother’s jeans before women’s versions were being made. They fit high on the waist, were boxy over the thighs, had a deep crotch, and ended with wide rolled cuffs. Repro ’40s jeans are not nearly as popular as ’50s styles that have a slimmer fit. Sometimes I have better luck buying men’s dark denim “work” jeans, rolling the cuffs, adding my husband’s belt and voila! Shop pants and jeans.

The best tops to pair with jeans are T-shirts, button-down pattern shirts (check, plaid, stripes) and dark colored blouses (navy, maroon, yellow, green). They could be short or long sleeved. I like short sleeve shirts with white collars and cuffs for a relaxed and almost western vibe. Shop shirts.

1940s casual jeans outfit – shirts, jeans, loafers

1940s Casual Outfit: Overalls

Overalls. You either love them or not. I love them because they are very comfortable to wear. I don’t love navigating the restroom with them. I am sure it wasn’t much different in the ’40s. Overalls were another work-to-play clothing item that makes a great casual outfit now. 1940s overalls were usually cotton twill or denim in lighter fabrics for summer. Dark to light beige and sometimes pinstripes were all common. They were worn over t-shirts or knit pullover tops, button down blouses, or nothing at all. Since ’40s overalls had a lot of coverage in the front and back, there wasn’t a need to wear a shirt underneath. Finding full coverage overalls can be tricky today. The current trend is for ’90s overalls that have narrow legs and a dropped bib. I look for overalls with a heart shape bib with button-on straps instead of hooks. Sometimes, I will buy a pair of hook overalls and change them out for buttons.

Like the pants above, overalls paired well with loafers and slip-on shoes, but I have also seen pictures of them being worn with sandals, Oxfords, platform heels, and wedges. Pretty much any shoe can go with overalls. Shop 1940s shoes.

1940s casual outfits with overalls

1940s Casual Outfit: Dresses

1940s dresses are some of the most casual of all the vintage decades. House or day dresses were usually colorful prints with simple A-line silhouettes. Summer dresses embraced the peasant dress or apron pinafore. I personally like shirtwaist dresses and wrap dresses in solid colors because they are the most versatile for adding accessories and layers like cardigan sweaters. A headband or hair scarf can also make a dress more casual as well as wearing socks with shoes (weird, but it works!) Shop ’40s day dresses.

These young and fresh “cute” dress styles make great casual ’40s outfits with just a pair of low heels, sandals, or slip-on shoes. I paired the dresses below with the Hallie wedge heels. I love mixing colors instead of matching everything. I think it modernizes the look a little bit for a vintage inspired casual outfit instead of true ’40s vintage.

1940s day dresses with low wedge heels

I test drove my new Hallie wedge heels this week when I attended my daughter’s Kindergarten graduation (#proudmama). I wanted to dress up a little for the occasion, but also be comfortable on a warm summer day. I wore my favorite floral summer dress (loosely ’40s style) and the red Hallie wedges, which have a similar floral pattern on the wedge. Because of how instantly comfortable they are, I didn’t need to “break them in.” I wore them all day without any issues. Usually when I wear new shoes, my feet hurt after a few hours. With Hallie’s low wedge, open toe, and comfort footbed, there was nothing to irritate my feet. If you want to read another review, check out Miss Hero Holliday’s blog and wonderful pictures.