A Complete Style Guide on Women's Hats and How to Wear Them

The Pillbox Hat 

The Pillbox Hat: A Timeless Classic

The pillbox hat, synonymous with elegance and refinement, emerged as a quintessential accessory in the 1950s and 1960s. Its simple, structured design adorned the heads of fashion icons like Jacqueline Kennedy, creating an enduring legacy of sophistication.

How to Wear a Pillbox Hat:

1. Crowning Glory: Position the pillbox hat slightly tilted to one side for a touch of whimsy. This classic placement enhances facial features and exudes a sense of confidence.

2. Match with Monochrome: Look for a pillbox hat in a matching or contrasting monochrome shade to your outfit. This creates a cohesive and polished look, ideal for formal occasions.

3. Hairstyle Harmony: Choose hairstyles that complement the sleek design of the pillbox hat. Elegant updos or a chic bob provide a perfect backdrop for showcasing this timeless accessory.

What to Wear with a Pillbox Hat:

• Shift Dresses: Embrace the mod aesthetic by pairing a pillbox hat with a tailored shift dress, capturing the essence of 1960s glamour.

• Tailored Suits: Elevate your professional attire with a pillbox hat, transforming a classic suit into a statement ensemble.

Styling Tips:

• Modern Twist: Fuse the classic with the contemporary by choosing a pillbox hat in a bold colour or featuring modern embellishments.

• Versatility in Veiling: Experiment with veiling or netting attached to the pillbox hat for a touch of mystery and allure, perfect for formal events.

The Cloche Hat

The Cloche Hat: Jazzing Up the 1920s Fashion Scene

The Roaring Twenties ushered in an era of liberation and glamour, and at the forefront of this sartorial revolution was the cloche hat. This snug, bell-shaped accessory became synonymous with the flapper style, embodying a sense of freedom and bold femininity.

How to Wear a Cloche Hat:

1. Low and Elegant: Position the cloche hat low on the forehead, allowing it to frame the face delicately. This low-slung style adds an air of mystery and allure.

2. Bobbed Hair Harmony: The cloche hat was designed to complement the iconic bobbed hairstyles of the 1920s. Consider tucking your hair neatly under the hat for an authentic flapper look.

3. Tilted Chic: Experiment with a slight tilt to one side for a touch of whimsy. This playful adjustment adds personality to your ensemble.

What to Wear with a Cloche Hat:

• Flapper Dresses: Embrace the spirit of the 1920s with a flapper dress, adorned with fringe or intricate beadwork, perfectly complemented by a cloche hat.

• Trench Coats and Gloves: Create a sophisticated, vintage-inspired look by pairing a cloche hat with a tailored trench coat and coordinating gloves.

Styling Tips:

• Contrasting Bands: Choose a cloche hat with a contrasting band or ribbon to add visual interest and draw attention to the distinctive shape.

• Velvet Luxe: Elevate your winter wardrobe with a velvet cloche hat, infusing a touch of opulence into cold-weather ensembles.

The Wide-Brimmed Hat

The Wide-Brimmed Hat: Embodying Glamour from the 1930s Onward

As the 1930s dawned, wide-brimmed hats took centre stage, epitomizing the allure of Hollywood glamour. These hats, adorned with dramatic brims, became a symbol of sophistication and mystery, favoured by leading ladies of the silver screen.

How to Wear a Wide-Brimmed Hat:

1. Face-Framing Flair: Position the wide-brimmed hat in a way that frames your face, allowing the brim to cast a flattering shadow.

2. Tilted Elegance: Embrace a slightly tilted angle for added elegance. This styling choice adds a touch of drama to your overall look.

3. Casual Chic: Contrary to its formal reputation, a wide-brimmed hat can also complement casual outfits. Pair it with a maxi dress or wide-legged trousers for a laid-back yet polished appearance.

What to Wear with a Wide-Brimmed Hat:

• Glamorous Gowns: Channel your inner movie star by pairing a wide-brimmed hat with a glamorous evening gown. Think satin, sequins, and floor-length elegance.

• Tailored Suits: For a sophisticated daytime look, pair a wide-brimmed hat with a tailored suit, creating a powerfully chic ensemble.

Styling Tips:

• Printed Perfection: Opt for a wide-brimmed hat in a bold print or pattern to inject a playful element into your outfit.

• Veil Vibes: Experiment with veiled wide-brimmed hats for a touch of mystique, ideal for formal events and special occasions.

Vintage Event Etiquette: Choosing the Perfect Hat

Navigating Goodwood Revival, Twinwood and Similar Vintage Events

For enthusiasts of the 1930s, 1940s, and 1950s, events like Goodwood Revival offer a delightful journey back in time, complete with classic cars, period fashion, and an ambiance that resonates with the golden eras of vintage glamour. Selecting the right hat for such occasions is not merely a fashion choice but a nod to the authenticity and respect for the bygone eras.

1. The Fascinator:

• Perfect for the 1940s: A dainty fascinator adorned with feathers, netting, or a small veil adds a touch of elegance. Pair it with a tailored suit or a tea dress for an authentic 1940s look.

2. Tilted Pillbox Hat:

• Ideal for the 1950s: Embrace the chic allure of the 1950s with a tilted pillbox hat. Pair it with a full-skirted dress or a tailored pencil skirt for a look reminiscent of mid-century sophistication.

3. Veiled Headpiece:

• Timeless Elegance for the 1930s: Capture the glamour of the 1930s with a veiled headpiece. Look for styles featuring delicate netting and pair them with bias-cut dresses or wide-legged trousers for a touch of Art Deco charm.

4. Wide-Brimmed Picture Hat:

• Versatile for All Eras: A wide-brimmed picture hat, adorned with bows or flowers, transcends decades and is a versatile choice. Pair it with a tea-length dress for the 1940s or a tailored suit for the 1950s.

5. Beret with a Brooch:

• Casual Chic for Any Era: A beret adorned with a vintage brooch can be a chic yet casual choice. Perfect for a day at Goodwood, pair it with a knee-length A-line dress for a timeless and comfortable look.

Styling Tips:

• Coordinate with Outfit Colours: Ensure your hat complements or contrasts with the palette of your outfit. This creates a harmonious and polished appearance.

• Consider Hair Accessories: Incorporate vintage-inspired hair accessories like combs, barrettes, or silk scarves to enhance your hairstyle and complement your chosen hat.

• Embrace the Theme: Embody the spirit of the event by embracing the thematic colours and styles associated with the 1930s, 1940s, or 1950s.

• Vintage-Inspired Sunglasses: Complete your look with retro sunglasses that match the era of your outfit. Cat-eye frames or rounded shapes can add an extra touch of authenticity.

Hat Accessories and Final Touches

Elevating Your Vintage Hat Ensemble

Selecting the perfect vintage hat is only the beginning; it's the accessories and final touches that elevate your ensemble from stylish to show-stopping. Whether you're attending Goodwood Revival or another vintage event, paying attention to these details ensures your look is authentically curated and impeccably styled.

1. Gloves:

• Elegance in Every Gesture: Pairing your vintage hat with gloves is a timeless choice. Elbow-length gloves evoke the glamour of the 1950s, while shorter, more practical gloves are reminiscent of the 1940s. Choose colours that complement your hat and outfit.

2. Vintage Handbags:

• Complete the Look: A vintage handbag adds the finishing touch to your ensemble. Search for styles popular in the era you're channelling—structured box purses for the 1950s, and sleek, practical bags for the 1940s.

3. Scarves and Shawls:

• Versatile and Chic: Adding a silk scarf or shawl can instantly transform your look. Knot a colourful scarf around your neck for a nod to the 1950s, or drape a shawl over your shoulders for a touch of 1930s sophistication.

4. Brooches and Pins:

• Personalize Your Style: Adorn your hat or lapel with vintage brooches or pins. Choose designs that resonate with the era, from art deco brooches for the 1930s to whimsical, nature-inspired pins for the 1950s.

5. Stockings and Hosiery:

• Seamlessly Vintage: Pay attention to your choice of stockings or hosiery. Seamed stockings were a staple in the 1940s, while the 1950s embraced sheer nylons. Select hues that complement your outfit and shoes.

Styling Tips:

• Match Accessories to Hat Detailing: Coordinate your accessories with specific details on your hat, such as matching the colour of your gloves to the hat's ribbon or choosing a brooch that echoes the hat's embellishments.

• Consider the Weather: If attending an outdoor event, bring a parasol or sun hat for practical elegance. For cooler weather, a fur stole or vintage-inspired coat can be both functional and stylish.

• Maintain Cohesiveness: Ensure a cohesive theme by aligning accessories with the overall era you're emulating. Consistency in details contributes to an authentic and polished vintage look.

• Vintage-Inspired Footwear: Complete your ensemble with shoes that echo the styles of the 1930s, 1940s, or 1950s. T-strap heels, Mary Janes, or classic pumps can be the perfect finishing touch.

Mastering Hat Etiquette and Posture

Navigating Social Settings with Grace

Wearing a vintage hat is not just a fashion choice; it's an expression of elegance and refinement. Mastering the art of hat etiquette and maintaining a poised posture enhances the overall impact of your vintage-inspired ensemble, especially in social settings such as Goodwood Revival.

1. Hat Removal:

• Indoor Etiquette: Tradition dictates that hats should be removed when entering indoor spaces, whether it be a charming tea room or a bustling event hall. Hold the hat at the brim when removing it, allowing others to appreciate your stylish entrance.

2. Greetings and Conversations:

• Maintaining Eye Contact: When engaged in conversations, tilt or lift your hat slightly to maintain eye contact. This gesture shows respect and allows for a more personal connection.

3. Seated Etiquette:

• Polished Poise: If seated, keep your hat on until you are settled. Once comfortably seated, you may choose to remove your hat and place it beside you. This maintains an air of refinement and avoids obstructing the view of others.

4. Handling Windy Conditions:

• Securing Your Hat: In outdoor settings, especially at events like Goodwood Revival, be mindful of windy conditions. Secure your hat with hatpins or clips to prevent it from flying away.

Styling Tips:

• Hatpins as Accessories: Choose decorative hatpins that complement your hat's style. These not only serve a practical purpose but also add an extra layer of sophistication.

• Practice Poise: Maintain an upright posture while wearing your vintage hat. Confidence and poise are integral components of pulling off a vintage look authentically.

• Hat Storage: Invest in a hatbox to store and transport your vintage hat safely. This protects the hat's shape and ensures it remains in pristine condition for future outings.

DIY Vintage Hat Restoration

Reviving the Charm of Vintage Hats

Preserving and restoring vintage hats not only adds a personal touch to your collection but also contributes to sustainable fashion practices. Embrace the art of DIY vintage hat restoration to breathe new life into classic pieces and showcase your creativity.

1. Cleaning and Dusting:

• Gentle Approaches: Use a soft brush or a clean, damp cloth to remove dust and dirt from your vintage hat. Be gentle, especially with delicate materials like feathers or netting.

2. Repairing Loose Threads:

• Needle and Thread Magic: Carefully stitch loose threads back into place, ensuring the repair seamlessly blends with the hat's original design.

3. Replacing Missing Embellishments:

• Crafting Authentic Details: If your vintage hat is missing beads, sequins, or other embellishments, consider replacing them with similar materials to maintain its authenticity.

4. Addressing Stains:

• Spot Treatment: Address stains promptly with appropriate cleaning methods based on the hat's material. Consult a professional if you're unsure about the best approach.

5. Reshaping and Steaming:

• Bringing Back Structure: Reshape your vintage hat by gently steaming it over a pot of hot water. Manipulate the hat into the desired shape and allow it to air-dry.

Styling Tips:

• Consulting Professionals: If your vintage hat requires extensive restoration or delicate repairs, consider consulting professionals who specialize in hat restoration to ensure the utmost care and expertise.

• Adding Personal Touches: Use restoration as an opportunity to add personal touches to your vintage hat. Consider adding a vintage brooch or ribbon to enhance its uniqueness.

Showcasing Vintage Hat Collections

Creating Stunning Displays and Storage

A cherished vintage hat collection deserves to be showcased with the same level of care and attention that goes into selecting and styling these timeless pieces. Learn how to create stunning displays and proper storage to preserve the beauty of your vintage hats for years to come.

1. Hat Display Stands:

• Functional Elegance: Invest in hat display stands to showcase your collection with sophistication. These stands not only keep your hats organized but also add a decorative element to your space.

2. Shadow Boxes:

• Artful Arrangements: Shadow boxes provide a creative way to display smaller hats or delicate fascinators. Arrange them in a visually appealing manner, creating a mini art installation on your wall.

3. Hat Hooks or Pegs:

• Vertical Elegance: Install hat hooks or pegs on your wall for an elegant and space-efficient display. This method allows you to rotate your collection regularly for a refreshed look.

4. Glass Cabinets:

• Curated Elegance: For a more formal and protected display, consider glass cabinets. These cabinets shield your hats from dust and direct sunlight while allowing you to admire your collection.

Styling Tips:

• Theme-Based Displays: Arrange your hats based on themes, eras, or colours. This creates visually appealing displays that tell a story and highlight the diversity of your collection.

• Rotating Displays: Periodically rotate the hats in your display to prevent prolonged exposure to light and dust. This also provides an opportunity to rediscover and appreciate different pieces in your collection.

• DIY Hat Rack: Get creative with a DIY hat rack using vintage-inspired hooks, a wooden board, and a touch of paint. This customizable solution adds a unique, personalized touch to your display.

The Art of Vintage Hat Hunting

Unearthing Hidden Treasures

Embarking on a vintage hat hunting expedition is a thrilling venture that can lead to discovering hidden gems from the past. Learn the art of navigating thrift stores, flea markets, and online platforms to uncover unique vintage hats that complement your style.

1. Research and Education:

• Informed Choices: Familiarize yourself with different vintage hat styles, materials, and designers. This knowledge will empower you to make informed choices and recognize valuable pieces.

2. Thrift Stores and Vintage Shops:

• Hidden Treasures: Explore local thrift stores and vintage shops for unexpected finds. Be patient, and sift through racks and shelves to unearth hidden treasures.

3. Online Marketplaces:

• Global Access: Browse online marketplaces for a wider selection of vintage hats. Platforms like Etsy, eBay, or specialized vintage stores offer a diverse range of options from various eras.

4. Estate Sales and Auctions:

• Exclusive Finds: Attend estate sales or auctions for a chance to acquire hats from personal collections. These events often unveil exclusive pieces with unique histories.

Styling Tips:

• Mixing Eras: Don't be afraid to mix hats from different eras to create a curated and eclectic collection. Experimenting with styles allows you to express your individuality.

• Collaborate with Milliners: Explore collaborations with local or online milliners who specialize in crafting vintage-inspired hats. This partnership can result in bespoke creations tailored to your preferences.

• Attend Vintage Fairs and Events: Participate in vintage fairs and events dedicated to fashion from specific eras. These gatherings provide opportunities to connect with sellers specializing in authentic vintage hats.

Vintage Hats for Wedding Guests

Elegance Adorned: Navigating Wedding Seasons with Style

As a wedding guest, choosing the perfect hat is not only a fashion statement but also a gesture of respect for the couple's special day. Vintage-inspired hats add a touch of sophistication to your wedding ensemble, allowing you to embrace the theme while exuding timeless elegance.

1. Summer Wedding Elegance:

• The Wide-Brimmed Sun Hat:

  • A wide-brimmed sun hat with lightweight materials like straw or organza is perfect for a summer wedding. Look for pastel shades or floral patterns to capture the essence of the season.
    
    

• The Cloche with Floral Accents:

  • For a more understated yet chic look, choose a cloche hat adorned with delicate silk flowers. This choice complements light, flowing dresses and adds a touch of romance.
    
    

• Vintage Fascinators:

  • Fascinators featuring feathers, bows, or lace are excellent choices for summer weddings. They are not only stylish but also provide a balance of elegance and breathability.

2. Winter Wedding Glamour:

• The Felt Fedora or Trilby:

  • Felted hats, such as fedoras or trilbies, are excellent choices for winter weddings. Choose rich, deep colours like burgundy, navy, or forest green to capture the cosy and festive atmosphere.
    
    

• Velvet Pillbox Hats:

  • Velvet exudes warmth and sophistication, making it an ideal material for winter weddings. A pillbox hat in plush velvet adds a touch of opulence to your ensemble.
    
    

• Fur-Trimmed Cloches:

  • Cloche hats with subtle fur trim evoke a sense of vintage glamour and provide extra warmth for a winter celebration. Pair them with a tailored coat or a faux fur stole for added elegance.

Styling Tips:

• Coordinating with Wedding Colours: If you know the wedding colour palette, consider incorporating those hues into your hat choice. This creates a cohesive look and showcases your attention to detail.

• Formal or Informal: Match the formality of your hat to the overall dress code of the wedding. A wide-brimmed hat may be more suitable for a formal affair, while a fascinator can be perfect for a semi-formal or casual wedding.

• Hair Styling Considerations: Coordinate your hat choice with your hairstyle. Updos work well with hats like pillboxes or fascinators, while loose curls complement wide-brimmed styles.

Vintage Hat Shopping Tips

Navigating Boutiques and Vintage Markets

Embarking on a quest for the perfect vintage hat is an adventure filled with treasures waiting to be discovered. Whether you're perusing boutique shops or navigating vintage markets, these tips will guide you in selecting the ideal hat that complements your style and stands the test of time.

1. Know Your Era:

• Research Styles: Familiarize yourself with the key characteristics of hat styles from the era you're interested in. Knowing the details will help you discern authentic vintage pieces from modern replicas.

2. Check for Quality:

• Examine Materials: Vintage hats were often crafted from high-quality materials. Look for well-constructed pieces made from materials like felt, straw, or silk. Check for any signs of wear or damage.

3. Assess Size and Fit:

• Try Before You Buy: Vintage hats come in a range of sizes, and it's crucial to find one that fits comfortably. Always try the hat on, ensuring it sits securely on your head without being too tight or loose.

4. Inspect for Damage:

• Check for Flaws: Thoroughly inspect the hat for any signs of damage, such as stains, loose threads, or missing embellishments. Minor flaws may be repairable, but be mindful of extensive damage.

5. Research Hat Designers:

• Identify Signatures: Some vintage hats bear the signature of renowned designers. Research common designer marks from the era you're interested in to identify potential hidden gems.

Styling Tips:

• Mix Vintage with Modern: Incorporate your vintage hat into a modern ensemble for a contemporary twist. Pair a 1950s pillbox hat with a sleek jumpsuit or a 1930s cloche with a tailored blazer.

• Customization Opportunities: Consider personalizing your vintage hat with subtle additions like a vintage brooch, silk ribbon, or feathers. This allows you to make the piece uniquely yours.

• Vintage Hat Care: Once you've acquired your vintage hat, follow proper care instructions to ensure its longevity. Store it in a cool, dry place and protect it from dust and direct sunlight.

Embracing the Timeless Allure of Vintage Hats 

A Final Flourish: Capturing the Essence of Eras

As we conclude our journey through the world of vintage hats, it's essential to embrace the timeless allure and enduring charm these accessories bring to any ensemble. Whether you're attending a glamorous event, celebrating a wedding, or simply adding a touch of vintage flair to your everyday style, a well-chosen hat has the power to transport you to a bygone era while making a contemporary statement.

1. Confidence in Expression:

• Wear It with Pride: Vintage hats are more than mere accessories; they are expressions of style, personality, and a celebration of fashion history. Embrace the uniqueness of your chosen hat with confidence.

2. Explore and Experiment:

• Dabble in Diversity: The world of vintage hats is vast and diverse. Don't hesitate to explore different styles, eras, and materials. Each hat tells a story, and discovering the one that resonates with you is a delightful journey.

3. Sustainable Fashion Choice:

• Eco-Friendly Elegance: Opting for vintage hats aligns with sustainable fashion practices. By giving new life to these timeless pieces, you contribute to a more eco-friendly approach to style.

4. Share the Passion:

• Influence and Inspire: Share your love for vintage hats with fellow enthusiasts. Whether through social media, vintage events, or personal gatherings, inspire others to appreciate the craftsmanship and artistry encapsulated in these pieces.

Styling Tips:

• Document Your Hat Journeys: Chronicle your experiences with each vintage hat, noting the occasions, outfits, and memories associated with them. This adds a personal touch to your collection and allows you to reminisce about your stylish adventures.

• Support Local Vintage Shops: Explore local vintage shops, markets, and boutiques to discover hidden gems. Supporting local businesses not only enhances your vintage hat hunting experience but also contributes to the preservation of historical fashion.

• Passing Down the Elegance: Consider the timeless nature of vintage hats as an opportunity to create heirlooms. Pass down your cherished hats to future generations, allowing the elegance and stories of the past to live on.

As you continue to incorporate vintage hats into your personal style narrative, remember that each hat carries a piece of history, a touch of glamour, and an invitation to express your individuality with grace. Here's to a future adorned with the enduring allure of vintage hats.