Vintage Winter Outfits- Ideas to Keep Warm

1938 Suede outfit

The desire to dress vintage (1920s, 1930s, 1940s, 1950s, 1960s, 1970s) in winter when temperate dips into freezing, snow piles up, and mud creates new challenges…. well it seems easier to go modern and bring back the cute vintage clothes in the spring.  Many ladies will do just that (myself included most days) but that doesn’t mean dressing warmly in vintage is impossible.

I follow a few vintage fashion forums and discussion groups online and picked up some great tips about how to dress vintage when it is cold/wet/rainy outside or inside when the boss cranks up the AC in summer (uggg I have lived that too many times.) Try a few of these ideas and see how you can keep the vintage style all year long.

Winter Dresses, Suits and Skirts

The bulk of vintage style dressing involves wearing a dress or skirt. I hesitate to wear vintage dresses in the winter because many of the fabrics seem too thin to keep me warm or they have short sleeves or skirt lengths are not long enough.

1944 rayon flannel dresses

When I do dress up in winter I look for wool or tweed dresses (easier to find in genuine vintage), velvet dresses for dressy occasions (mmm warm and toasty), and flannel, corduroy, or knit dresses with sleeves for day to day styles.

Naturally, I prefer long maxi dresses over knee-length styles but with some warm tights, short dresses are wearable. Short sleeve and sleeveless jumper dresses (pinafore dresses) can be worn with a long turtleneck shirt or blouse underneath.

1958 Chanel Style Suits

Two to three-piece suits (jacket, skirt, vests) are especially good for office and professional environments.

Felt skirts, such as 1950s poodle skirts or cotton quilted skirts are also nice and toasty options without the heavy weight. A big plaid pattern is very winter-y too.

Longer length wool tweed, checks, plaid and herringbone pattern materials in neutral colors are back in style as part of the Edwardian revival/cottagecore look. These work really well for most vintage decades too.

Tips: If you live where it is very cold and need multiple extra layers underneath you may want to size up your winter dresses and skirts from your summer size.

High Waist Winter Pants

I live in jeans, pretty much year-round. They are a vintage classic as well although the earlier decades preferred wool slacks and flannel-lined jeans in winter. Paired with a long sleeve bow blouse, flannel boyfriend shirt or knit sweater top, pants can be dressy or casual. The wide-leg styles offer plenty of room to layer long johns and tights underneath.

Overalls and jumpsuits are also roomy and not as drafty as separates can be (although a beast to wrangle in the restroom.) I am partial to denim overalls and jumpsuits (boiler suits) that have become popular again. Grab ’em while you can!

Vintage ski clothes such as wool snow pants and bib overalls are still available in some vintage thrift stores. My good friends ski Tahoe in the brightly colored ’80s ski clothes. You can’t miss them on the slopes!

Tip: Workwear has mostly gone unchanged in the last 50 years. Many overalls, pants, wool shirts, flannel shirts and leather boots are as classic as ever.  If your work or leisure life calls you outdoors consider dressing in vintage or new workwear. Read about 1940s workwear, history of pants and western wear. 

Vintage Coats and Jackets

A good long wool coat is an essential piece for a winter wardrobe. Luckily they can be pretty easy and cheap to find in thrift stores. You can find new overcoats as well, some with faux fur collars. These are usually warmer than vintage reproduction coats which have all the style but not always the warmest materials.

Raincoats too can be purchased inexpensively. Both can be made more water repellent with a spray-on coating. For severe rain its best to leave the wool coats at home or layer under a plastic poncho or clear vinyl rain jacket. While your at it a vintage umbrella is a must too!

Short winter jackets are nice pieces to have indoors or in cold but not too wet climates. Try a 30s blanket coat, 49er jacket, down jacket, 50s swing coat, chore coat, bomber jacket, pea coat, belted mackinaw coat, and leather or suede jackets. These are all timeless and yet each has a distinct classic but casual style for winter. Shop coats and jackets. 

Tops, Sweaters and Jumpers

You have read it several times already. Layers are key to winter. A good plaid flannel button down shirt is perfect for cozy winter outfits. Turtleneck or mockneck jersey knit shirts in neutral colors are also essential for layering under dresses.  Real silk blouses are surprisingly warm. Shop tops. 

Sweaters, jumpers and sweater vests are the perfect layering piece that stay on all day. Fuzzy knit longs sleeve tops, turtle necks, and thin pullover sweater-shirts are ideal as the base layer. Cardigan sweaters and twin sets, chunky knit fisherman sweaters, sweater vests and faux fur/shearling lined vests are second layer options. See vintage sweaters 1900-1930s and 1940s to 1960s.

Detachable collars and dickies are yet another type of first layers that are slipped under sweaters and dresses. They make open-neck tops more modest and covered up=warmer. I save old blouses that are worn out and cut wide around the neck making a dicky that I can continue to wear with other dresses and tops.

Knit boleros, shrugs, crop jackets, capelets (short capes) and even vintage bed jackets can all be used as light layering pieces instead of a cardigan sweater.

Tip: To maintain a figure, wear a belt over the top layers.

Vintage Winter Under Layers- Tights to Petticoats

Winter underwear are the most important pieces of vintage winter outfits. It is amazing how one thin cotton camisole or tank top is all I need to be toasty warm. Colder weather means needing more under layers which is fairly easy without adding too much bulk.

For the legs:

• Stockings – Want to wear your pretty vintage stockings? Double them up (may not look neat with back seams) or wear one backseam pair over another non-seamed pair.
• Ice Skating Tights – I LOVE ice skating tights in a skintone color. They are my go-to stocking replacements for winter or cool summer evenings.  So warm and very durable.  Ballet or dance tights are another good option that are thinner but long wearing.
• Fleece-lined leggings or tights are really cozy against the skin. Soft merino or cashmere wool too. Not vintage but between tall boots and a longish skirt or dress they won’t be noticeable. Snag Tights (UK) are highly rated and size inclusive.
• Thermal tights- Another suggestion is for thermal tights, silk tights, velvet tights, or cotton ribbed tights/sweater tights. Each is a vintage style worn in the winter. The texture makes for an interesting legging with shorter dresses and skirts.
• Very tall thick socks- cotton or wool blend. If you don’t like tights, wear over the knee socks or over the calf socks instead. Sock Dreams has almost every style imaginable.
• Spats / gaiters / leg warmers made of knit or wool felt are like tall socks but worn over shoes for less bulk and easier removal once inside.

For the top:

• Silk camisole, cotton tank top, or cotton ribbed men’s undershirts each are a welcome first layer. Snug against the skin they are just what you need.
• Long john sets with sleeves- such as those made of silk or a bit thicker thermal cotton or merino wool are better for all over body warmth. You can cut off the legs to whatever length you need to go under your dress/skirt.

1938 knit slips

For the bottoms:

• Bike shorts/yoga shorts are a must if you don’t wear tights or long johns. Vintage tap pants or bloomer undies do the same job.
• Slips– a full dress slip or half skirt slip not only helps your dresses hang better but adds a thin layer of warmth. Skirt slips can be made of flannel, quilted cotton, knit, wool, jersey- you can make whatever you need to be warm.
• Petticoats – nylon fluffy petticoats are surprisingly warm- layer 2 or 3 for fullness. Quilted cotton petticoats are even warmer (and cooling too.) Making a petticoat out of flannel is not authentic to the era but no one will know! Heavy jersey knit is more period correct but harder to find fabric for.

1944 winter underwear

Underwear and Bras:

• Thick cotton granny panties and sports bras tend to be warmer than nylon/polyester type lingerie. Full coverage bras are better than sexier lingerie.
• Shapewear can do double duty for warmth and figure. Vintage lingerie such as corsets and girdles will naturally provide a warming layer- although I find synthetics to not breath and therefor I get a clammy feeling when warm.

Read the history of lingerie from the 1920s, 1930s, 1940s, and 1950s

Vintage Winter Accessories

Hats

The most heat is lost through the head so keep it all in with a winter hat. Knit beanies, knit or felt berets, caps with earflaps and fur lined bucket hats are the most casual and wintery but I don’t like to wear them once inside. I prefer vintage felt hats like a cloche hat or fedora to keep on all day. Shop hats. 

• A turban hat or tied turban scarf is another popular headwear option for winter and summer.  I prefer pure silk so that it doesn’t frizz my hair.
• Ear muffs- these are so cute!
• A plastic rain hat/hood is a welcome accessory in wet weather that protects freshly styled hair.
• I also really like silk or wool headscarves to wrap around my head and under the chin like a kerchief or babushka. They keep my ears warm. A snood (scarf and hood in one) does the same thing and was worn in the mid-century quite a bit.
  

  1941 pattern headscarves

Scarf

Scarves are so versatile and warm. Thick chunky knit scarves are great for outdoors. Soft wool or cashmere scarves keep necks wrapped up. Thin silk or wool scarves can be wrapped around the neck and tucked under a blouse or sweater.  Fur, if you are ok with using vintage, are exceptionally warm scarves, coat collars, and hand muffs.

1930s neck and kerchief scarves

Wraps

When you don’t need a full coat, such as indoors, a wrap/shawl/cape can be what you need to stay warm but free. I wear a light wool shawl at my desk in winter. It is thin but wow !does it help me keep warm. Now I just need to find something to keep my hands from getting chilled while I type.

If a cape or shawl is too loose try belting it around your waist. Or if it is long enough cross in front and wrap it around to the back and tie or pin it behind you.

Read more about winter scarves/wraps/shawls.

1953 scarf wraps

Gloves

The trick to gloves in winter and getting a pair that is long enough. It helps if gloves are long enough to meet the edge of a sleeve. Other than that any style that you love can be integrated with your vintage outfit. I like fur cuff gloves, knit fingerless gloves, wool gloves, lined leather gloves and more importantly these days- a touch screen friendly fingertip! Shop gloves or learn about glove history.

A fur muff is nice to carry if you are constantly taking your hands out of your gloves or if your coat doesn’t have good pocket placement.

1931 gloves, rainbow mittens

Winter Boots and Shoes

The final piece is a big one. Shoes and boots designed for whatever weather you will encounter. This is where practical and warm modern winter shoes usually outweigh the desire to look vintage.

Vintage boots were not too warm or water proof. Women had to wear several layers of socks or put plastic bread loaf bags between socks and boots to keep dry.

Rubber overshoes were made to wear over nice dress shoes or heels were carried separately and rain boots/galoshes were worn to and from places. It was an ordeal and very few were very fashionable looking.

1955 fur lined winter boots

Of the vintage styles you can find these are still in stores:

Lace up granny boots– ankle to calf-length lace-up boots with a modest heel have been in style for over 100 years. They may not be great in snow or very wet leather but for general cold, they will look cute and be vintage.

Hiking boots– Over the calf, tall, lace up boots, were worn by women for outdoor sports like hiking, hunting, fishing etc especially paired with breeches/jodphurs/plus four knickers. They are very hard to find and expensive but well worth it as an investment piece for all seasons.

Snow Boots with a leather or felted wool body have the most vintage look. Fleece lined, faux fur lined, or shearling boots, especially with bits of the lining making a cuff at the top are the most vintage looking.

Snow Boots – LL Bean, Doc Martins, Sorel, Keens, UGG and others.  I have many vintage style boots linked here. See examples of vintage  winter boots. 

Work boots – Industrial designed leather work boots also make excellent winter boots. They may not be pretty but they are practical, made of sturdy durable materials, and roomy enough for layers of socks.

Chelsea Boots- Since the Victorian era pull on boots with elastic side panels, later called Chelsea boots, have been a practical boot to keep by the door for yard and garden work. For vintage outfits, I think they work best with workwear.

Duck Boots –  Waterproof duck boots have been around for over a century yet.  While they were not as popular as other styles their prevalence today makes them a timeless choice that are easy to buy locally.

Wellington Boots – Pull on wellington boots or rubber rain boots are excellent for wet weather.

As for non-boots, a pair of oxfords is essential for most dressy outfits.  Avoid any with brogue (decorative air holes.) Penny loafers and other classic slip-on shoes are also great for casual outfits. A pair of rubber overshoes can help preserve nice heels while briefly walking through wet terrain.

Winter boots, vintage style for 2020

Winter-Friendly Brands

• Emmy Design of Sweden- High quality knitwear, coats and jackets.  Highly rated winter clothing in the 1930s to 1950s styles.
• MS Pomeranz – London designer includes many wool dresses, jumpers and coats in warm wool.
• Maya Hotenko Dress – Ukraine designs has wool and corduroy vintage inspired dresses in her shop
• Irish Sweaters called Arron sweaters are made of heavy knit wool. They are incredibly warm and never-go out of style.
• Pendleton – Almost all clothing is wool. Coats, jackets, sweaters, pants will last a lifetime. Vintage Pendleton is collectable for these reasons.
• LL Bean- Since 1912 LL Bean has been making winter friendly clothing. Their Signature collection is remakes from their original designs.  Sweaters, jackets, boots and flannel lined jeans.
• more… Do you have recommendations for this list?

More outfit ideas for winter:

1920s Winter Outfits

1930s Fall and Winter styles

1940s Fall and Winter outfits

1950s outfit ideas for all seasons