Vintage Hat styling guide for women
How to properly wear a hat (and convince yourself that you DO look good in hats)
Change the Tilt / Angle
Experiment with the angle of your hat. A slight tilt can add flair and personality to your outfit, even a pair of jeans and blouse. Tilt it to the side for a playful look or angle it forward for a more classic feel.
Wear with Confidence
The key to rocking a vintage hat is confidence. Own your style and attitude while wearing it. When you feel good, you’ll look good, too!
Match the Era or Outfit
Vintage hats come in various styles from different decades. Match your hat to the era you love or that complements your outfit. For example, a cloche hat is perfect for a 1920s look, while a wide-brimmed sun hat can evoke the 1950s.
Consider Hair Length
Short Hair: Showcase your hairstyle by wearing the hat slightly back on your head, allowing hair to frame your face, especially if you have bangs.
Long Hair: Tucking it into the hat can create a polished, sophisticated appearance. Loose waves are also gorgeous with many vintage hat styles!
Play with Hairstyles
Pixie Cut: With a short pixie cut, consider wearing the hat low on your forehead, creating a chic, retro look.
Curls and Waves: Soft curls or waves beautifully frame your face when you wear the hat
Updo: An updo, like a bun or chignon, pairs wonderfully with a vintage hat, especially for formal occasions
Choose Complementary Colors
Consider how the hat color complements your outfit and skin tone. A coordinated color scheme can make your vintage hat pop. Not sure what complementary colors are? See Canva’s easy-to-use color tool.
Experiment with Outfits
Don’t limit your vintage hat to just one style. Try it with different outfits, from casual jeans and a t-shirt to elegant dresses. It’s all about how you style it!
Hat Pins and Ribbons
Add hat pins, brooches, or ribbons to enhance your hat’s appeal. These accessories can add a touch of glamour and individuality to your vintage look.
Vintage Hat FAQ
According to one of my favorite vintage hat sites, Vintage Dapper Day:
“Hats are generally considered vintage if they can be associated with a specific decade, such as the cloche hats of the 1920’s or the pillbox hats of the 1960’s. Hats often reflect the social climate of the nation at the time. For instance, the pillbox hats were associated with the formal style of the 1960’s, while the more military-looking hats of the 1940’s reflected the military feeling of the country during World War II.”
Antiques are generally at least 100 years old. Vintage items are older than 20 years, but younger than 100 years.
Generally, if a hat is more than 20 years old and younger than 100 years old, it falls under the definition of vintage.
It’s a bit of an educated guess…and I’m not an expert, just a passionate vintage hat lover with a lot of hats. Here are some of the basic key distinctions to help you date a hat, based on my experience and research:
Victorian and Edwardian Hats (19th to early 20th century):
- Look for indications of wear; brand-new hats are likely reproductions.
- No sweatband, but usually have a lightweight lining with a drawstring.
- Wire frames or reinforcement may be present, especially in the brim’s outer edge.
- No v-shaped “clips” or inner caps to hold the hat; held on with hatpins.
- Sewing machines were in use, so machine stitching might be visible.
- Decorations are sewn on, not pinned or glued.
- Sometimes have the maker’s name on the lining; ribbon-style labels are rare.
- No sweatband; most have a lining that is not gathered in the center.
- Popular cloche design, which can be confused with the 1960s style.
- Labels may be sewn into the hat or embroidered on the lining.
- Some hats may slouch to one side or have Art Deco-inspired designs.
- Wide-brim hats called “picture hats” are popular again (last era of popularity was Edwardian 1901-1919).
- Lining may be absent in some hats, while others have small ribbon labels.
- Early plastic decorations like celluloid or Bakelite are used.
- Lining is unusual unless the hat is made in France.
- “Doll” or “toy” hats perch over the forehead; some dealers call them “tilt” hats.
- Hats with chignon rings or ribbons are worn, fitting around the back of the head.
- Hats with hairnets or “snoods” are seen, along with hats with wimples.
- Plastic decorations become more common, especially after WWII.
- Hats are usually not lined but have a sweatband.
- Tiny plastic combs may be sewn in to help hold the hat in place.
- Labels are ribbons in the sweatband.
- Some hats have v-shaped “clips” or inner caps to secure them.
- Feathers may be glued onto hats.
- Small pillbox hats are introduced in the late ’50s.
- Pillbox shape becomes larger, and Mod styles with bright colors are popular.
- The cloche style returns, worn on top of the head.
- Lining may be absent, but sweatbands are common.
- Labels are often on ribbons, sometimes glued in.
- Utilitarian hats for shade or warmth are worn; fashion hats decline in popularity.
1980s to the Present:
- Fashion hats return, often for special events like weddings.
- 1980s period films like “Somewhere in Time” and “Anne of Green Gables” repopularized some of the large Edwardian picture hats (like Rose’s hats in Titanic)
- Hat construction remains similar to the 1970s, with more glued-on decorations.
- Hats usually have labels, indicating the country of origin and fabric content.
My favorite delineation between vintage and retro (aka reproduction/repro) comes from a handcrafted furniture shop:
“Retro and vintage can be commonly confused. The easiest way to tell the two apart is to remember that retro goods are current reproductions or imitations, while vintage is genuinely older items.”
Retro hats are typically more affordable and easier to find than vintage hats. So, many of us who love vintage hats (and have a limited budget) end up buying retro hats that emulate the look of our favorite vintage eras.
If you have a large budget and want to start a vintage hat collection, I would go to estate sales in older parts of town, antique stores, and other auctions. There are a LOT of vintage hats sold online (I’ve bought many myself) at sites like eBay, Etsy, and Poshmark. But keep in mind that many of these hats may actually be RETRO, not Vintage, especially if they are in like-new condition. I’ve seen brand-new hats sold on Amazon as “vintage”, but they are really retro hats. But if you want a vintage-looking hat at a reasonable price, buying online “vintage” hats can be a fun, cheap way to start your hobby.
A milliner. There have been numerous hat designers over the decades, including small craft millinery shops, so I won’t list them all here. Some of the modern milliners who focus on craftsmanship include Lock and Co (350 years of hatmaking in England), Christys’ London (250 years of traditional hatmaking), and Borsalino (the oldest Italian hatmaker still designing today).
Some of my favorite retro hats come from FeltPoint, The Vermont Country Store, Village Hat Shop, The Irish Store (I own this wool hat and wear it everywhere), Award Millinery Design, Scala and Betmar (excellent everyday quality hats for women)
You can either tuck your hair up into a large hat (showing no hair) or show at least a little hair. When I’m in a fibromyalgia flare, I sometimes hide all hair under a hat, other times I will show a bit of my 20s half bob haircut. It’s up to you!
The answer varies based on your personal style, your face shape, your budget, and how sensitive your head is.
Working on a computer all day leaves my eyes dry, so I can’t wear contacts, only prescription glasses. Once I found my signature red cats eye glasses, I’ve had fun pairing them with all of my vintage and retro hats. The biggest issue I personally experience involves the rubbing of a tight hat band against the glasses above my ears, which is especially annoying near my craniotomy scar.
Traditionally, ladies would use hat boxes to transport their vintage hats. For the average flyer in coach, it can be pricey to bring that extra piece of luggage. My solution: stack the hats on my head and go!
Vintage hats by era
Love vintage and reproduction hats? Check out my personal hat collection. Don't look good in hats? Try my styling guides for vintage hats for women before you donate that gorgeous pillbox, bucket, fedora or beret.
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