How to Wear 10 Vintage Hats: For Day, Evening, Fun, Church & Picnic

by Sammy in 18 Comments — Updated February 11, 2020

Last week’s episode of Sammy D TV said it all: Seek out vintage in the closet of your elderly loved ones.

But what I failed to share were the complete goodies of one particular successful venture into the closet of a former high school classmate’s 90-year-old grandmother. Actually, it was her attic. Of her 1920s three-story home in the historic section of Lancaster, Pennsylvania near the home of former president James Buchanan.

Besides the fact that it was the perfect setting to find the vintage eye candy below [start scrolling … you won’t be able to stop], it was the perfect example of how one woman’s trash is another woman’s treasure. As I explain in the video, your grandparents/great aunts/uncles/mom/dad/old college professors just don’t know the value of what they consider to be “just collecting dust.”

Even my friends over at Pickles and Coffee recently scoured some sweet vintage sunglasses from their grandmother. Good work, boys!

With the first Sammy Davis Vintage Lovin’ Benefit Sale [and one year anniversary!] fast approaching, it’s about time that I start giving you a tasty preview of the currency of my constant traveling in the Camry.

All hats are available for sale in my store on Market Publique. Visit and drool over additional pictures, and feel free to shoot me an email with any questions.

1.) FOR DAY: Miss Red Lace

Perfect for: Brunch with the ladies

Pair it with: A black shift dress or A-line pencil skirt for sophisticated sass

Vintage currency: $50, + shipping if applicable

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Above: Union tag proving all-American made

2. FOR FUN: Miss Flower Child

Perfect for: Shopping in SoHo [or insert chichi urban shopping district here]

Pair it with: Sweet and subtle neutrals — off white, lilac, light yellow, light blue

Vintage currency: $60, + shipping if applicable

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Vintage education: “Millinery” refers to hats sold by a hat maker. From Wikipedia: The origin of the name is likely the Middle English Milener, as in an inhabitant of Milan or one who deals in items from the Italian city known for its fashion and clothing. Do you know a hat maker company today? Neither do I.

3. FOR OH LA LA: Miss Eve of the Garden

Perfect for: Sexy sightseeing

Pair it with: Bright florals, red lipstick and pumps

Vintage currency: $50, + shipping if applicable

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4. FOR EVENING: Diva Darling

Perfect for: An evening out at the theater [or insert fancy schmancy event here]

Pair it with: That LBD hanging in your closet right now

Vintage currency: $50, + shipping if applicable

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5. FOR EVENING: Ribbon Rendezvous

Perfect for: Sipping at a wine bar

Pair it with: Lace & pearls

Vintage currency: $50, + shipping if applicable

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6. FOR EVENING: Black Scarlett & Lace

Perfect for: Dinner with SO’s parents

Pair it with: Lace shell, cropped blazer, and high-waisted skirt [in whatever color so desired]

Vintage currency: $60, + shipping if applicable

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7. FOR HOLIDAY: Strawberry Shortcake

Perfect for: Easter, May Day, or picking strawberries in a strawberry patch

Pair it with: Wide-leg white jeans and a V-neck tee

Vintage currency: $40, + shipping if applicable

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8. FOR CHURCH: White Innocence

Perfect for: Whenever you need to wash the guilt away

Pair it with: Pretty pastels and fishnets

Vintage currency: $45, + shipping if applicable

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9. FOR THE GREAT OUTDOORS: Wicker Wits

Perfect for: Picnics in the park

Pair it with: Skinny jeans and your favorite band T-shirt

Vintage currency: $35, + shipping if applicable

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10. FOR THE BOYS: Fantastic Fedora

Perfect for: Looking hotter than you actually are

Pair it with: Distressed denim, penny loafers, a white tee, and corduroy blazer

Don’t wear it to: A party where a drunk girl will flirtatiously take it off your head, and you’ll never get it back

Vintage currency: $30, + shipping if applicable

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THE LOST ART OF HAT BOXES

Along with the fantastic find of 10+ vintage hats, I came across a few nearly mint condition hat boxes. Have you ever SEEN a hat box sold in stores? Neither have I.

This one speaks to me – since the art depicts 5th Avenue, New  York. There is some writing in pencil on the top of the hat box, but the inside and construction is perfect.

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Note the street sign that says “5th Avenue.”

Are you digging these hats? Which one is your favorite? Let me know in the comments below — I’m interested to get feedback on what you’d ACTUALLY wear!

18 thoughts on “How to Wear 10 Vintage Hats: For Day, Evening, Fun, Church & Picnic”

  1. The first one is my favorite–the color is so pretty. The leafy one is also really interesting. I’m a sucker for a good hatbox and have one from when good ol’ Woody’s reigned supreme in DC. It’s got the DC skyline all around it and just warms my heart.

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  2. houndstooth fedora… with a feather!!! WOWZA

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  3. i can definitely get down with Ribbon Rendezvous! and i love that you brought up the lost art of hat boxes. i LOVE hat boxes – but they are just so hard to come by these days! stay fabulous xx

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  4. white innocence is my favorite!

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  5. I would definitely wear 5, 4, 3, and 1 (I also love 7, although I’d have to see how it would work on my head since that style depends on the size for me). I actually have one that’s almost identical to #6 and which I wear ALL the time…and yet for some reason I almost want a second one. Also, I want to put Eugene in the fedora although I just showed it to him and he said “nope.” I’m emailing you now. :)

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  6. I would definitely wear 10, The Fantastic Fedora, even though I’m a girl. I LOVE fedoras, especially on guys!!! =3 I’d love it if hats still came in boxes, that’d be awesome!

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  7. Makes me wish I had more guts to wear hats. I usually take them off after ten minutes of feeling like everyone is staring at me. These are so pretty

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  8. Wow this is a great resource.. I’m enjoying it.. good article

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  9. Wow! I love this feature and I love these hats!

    My favorites are the red one with the bows and the pink and green one… So tempted to hit buy now!!!!

    I think hats totally make an oufit: wear something simple, add a hat and you look instantly fabulous!

    Are you selling the hat box? I love love love it!

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  10. …..I’m trying to decide between about 20 different hats I’ve got on my “Watching” list on Ebay…

    I’m thinking about getting several fitted jackets–one denim, one brown, one light-colored like beige or tan, one black (plain black and one velvet)…..and using jeans and a tee as suggested above.

    I’m a complete vintage hat virgin and need to start off slow…I’m still trying to figure out in what context to wear some of the dressier hats. There’s simply not much going on in my local, event-wise. They’re too unique and beautiful not to be worn at all!

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  11. Terrific work! This is the type of information that should be shared around the web. Shame on the search engines for not positioning this post higher!

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  12. The Vintage styles are very popular this year. Just about every Celebrity is wearing these styles.

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  13. Needs must when the devil drives.” – nach William Shakespeare Ende gut, alles gut, 1. Akt; dort: “He must needs go that the devil drives

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  14. how do you wear hat Number one? i have one a lot like it and it’s killing me i don’t know the correct way to wear it!

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  15. White Inocense is my favorite. I always wear a hat. It started with my Red Hat group now I have hats in every color. Don’t be afraid to wear a hat it fun and you will get a lot of compliments. Try different ways of putting on the hat you have and see what looks right on you. A lot of hats look good with a slight tilt some need the brim angled have fun with them.

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  16. great ideas.

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    • Thanks Robin! Do you own a vintage hat?

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  17. Hello! I was browsing your site on tips on how to wear pillbox hats…i ordered one from Etsy…it has a faux white rose on top, its one of those open hats, then a small veil framing the eyes. Im afraid of looking costumey buy just wearing this piece. In addition, i want to wear crocheted wrist gloves to add sass, but im afraid im pushing it. I got a very simple basic dress so i could accessorize. Boatneck, low back, skater-style skirt. Then satin peep toe pumps. Any tips on how i dont look like im starring in a play? Its actually for a dinner…the invite says dress elegantly and stylish…and originality is welcomed.

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