The 1920s and 1930s are mostly associated with flapper dresses and Hollywood glamour. During the daytime, dresses were still the primary outfits but that doesn’t mean they were the only thing women wore. I had a few readers ask what kinds of casual 20s clothing or 30s menswear-inspired looks they could wear that involved pants, not dresses. Using thrifted and purchased clothes, I put together some 1920s outfits with the help of my sister as my model that embrace the rebellious anti -flapper or masculine women’s looks of the 20s and 30s.
1920s Outfits – Tweed for Fall
1920s fall style with tweed pants, jacket and cap- menswear inspired
1920’s Paris Woman in Pants
I love the belt back of this jacket
The first 1920s outfit was inspired by my research of women wearing pants.  Some young women decided to adopt menswear as their clothing style as a statement against the flapper movement. Sometimes called “New Women” they dressed casually in men’s knickers or wide leg pants, collared blouses, long neckties, 8 panel caps and men’s jackets. Plaid or tweed pants and jackets were especially common in fall or winter while solid color cotton knickers with tall socks were worn in summer. A pair of low heel oxfords were neither feminine or masculine and they completed the outfit.
For my DIY 1920s outfit, I found a pair of wide leg plaid brown pants (90s vintage), peter pan collar blouse with black tie in a rust color from Forever 21, tweed check coat from Pendleton (a repro from their original 1910s line), plaid vest and tweed flat cap. Whenever I source menswear clothing for women I try to find them in women’s clothing but sometimes it is easier to buy them in men’s. Vests, for example, are not “in style” for women but men’s 20s vests work just fine.
1920s tweed outfit with vest
Casual 1920s Outfit
I was very excited to find a 1910s-1920s style cardigan sweater at the thrift store. The chunky knit deep burgundy red cardigan with oversize collar and big buttons jumped in my cart. Paired with the same wide leg pants and flat cap above it easily makes a 1920s casual outfit perfect for fall and winter’s cool days. I could wear the sweater with a long wool skirt too and have a second early 20s outfit. For spring, wearing the sweater unbuttoned with a belt around the waist and over a flowing pleated skirt takes the look to a sporty relaxed style.
A new (thrifted) sweater with large collar was the perfect top for this winter 20s casual style.
1921 winter knit cardigan sweaters
Here is another outfit I made using a 1920s style cardigan sweater over a blouse and pleated skirt. It is one I wear often (although usually with jeans, not skirts.) Striped varsity sweaters are in fashion now so this look is easy to attain. Paired with a cloche hat and two tone oxfords (saddle shoes would work too) the look is both vintage and modern casual.
My 1920s inspired casual sporty look: cardigan sweater over a loose blouse and pleated skirt with two tone oxford shoes.
1930s Pantsuit Outfit- Marlene Dietrich
A reader wanted help finding a 1930s style Marlene Dietrich suit. That is no easy feat but I was up for the challenge. Marlene usually bought men’s suits and had them tailored to her body. Most women at the time who adopted menswear clothing did this as well. Women’s menswear was not a big enough fad for mainstream clothiers to produce them for the masses.
For accuracy, purchasing a 1930s reproduction suit, sewing a suit, or buying a vintage men’s suit and tailoring them is the best option. For the rest of us on a budget, you can adapt a thrifted women’s suit to the look easily, that is IF you can find a suit to begin with. I found this grey check suit but it was the only option that didn’t look totally out of place/ the wrong decade in the several stores I shopped. I searched online too but most modern suits have skinny pants (not wide leg) and plain blazers that resemble ’60s fashions, not 1930s. Finding a menswear 1930s outfit was a lot harder than I expected.
Marlene Dietrich in a pant suit
1930s menswear suit outfit
Removing the jacket and wearing the pants with a white button-down collared shirt, dark necktie and vest creates the same masculine 30s oufit but without the difficulty of finding a matching suit set. Wearing a fedora hat instead of cloche transforms it into a gangster mol costume (wives of gangsters / female gangsters.)
1930s menswear or gangster mol look
1930s Outfit: Bonnie Parker
A 1930s Bonnie Parker costume
Speaking of 1930s female gangsters, the most notorious of them all is Bonnie Parker, partner to Clyde Barrow. She did not wear men’s clothes, at least she was never photographed in them. She always had a 30s dress or skirt and top separates with a pair of heels and freshly styled hair. Very lady like!
For my Bonnie Parker outfit, I found a tea length gored skirt on Amazon and paired it with a chevron knit sweater, T strap shoes, and 30s wig. I am pretty proud of this one. It is simple, yet accurate and very wearable today, perhaps without the wig.
1930s Bonnie Parker outfit with a skirt and knit sweater
These 1920s and 1930s outfits should give you some ideas for menswear inspired women’s looks. Do you have a look you need help with? Ask me anytime!