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Zoom-in on fedora with zipper flower

Hats have three functions: Protection from the cold/wind, identification of the wearer as a member of a group including their rank, and making a style/fashion statement. This guide covers how to use fashionable hats to up your style. In other words, use them as a statement. Read how to look incredibly stylish with hats.

  1. Hat Trends of the 20th Century
    • Headgear When I Was a Kid
  2. How to  with Look Stylish Hats Today
    • Best Styling over 40
  3. Which Hat to Wear with Which Clothes
    • Further Inspirations to Look Stylish with Hats
    • How to Wear Vintage Styles
    • Pom-Pom Hats Ideas


Disclosure: This post has affiliate links.


Hat Trends of the 20th Century

January 15 is National Hats Day. In fashion history, hats have played a role  indicating societal status. They used to have a place all year round perennially. They were a big Do in the first half of the last century.

Good news for hat-lovers: They are having a comeback right now.

My late mom once told me that my grandma (her mom) had her hats altered every season to have the latest trend. The hats usually had a neutral color and the embellishments like feather, blossoms, etc. including the hat trim were exchanged to match the latest trends in color and style.


Head Gear When I Was a Kid

When I was a kid, my grandpas wore straw fedoras in summer and felt fedoras in winter. In summer, they paired their hats with a light blazer, in winter with a straight wool or loden coat. My parents wore hats only in the cold season, and only when it was cold. Mom had a beautiful gray hat with feathers that I adored. Dad had a small hat collection including a leather driver’s cap, leather and wool Prinz Heinrich Mützen (in the US these head toppers are called fishermen hat), a felt fedora, a Bavarian hat, a leather Australian hat, and various pom-pom hats. The latter, he would only wear in the yard in early spring or late fall or when walking along the beach on a windy spring or fall day.


fashion blogger in plaid skirt under shearling coat wearing a green beret
Side view of outerwear described below


over 50 years old Alaskan fashion blogger in winter look with shearling coat and green beret
Vittari shearlings coat, LeatherCoatsEtc beret, GNW tights, Clark booties, LV bucket bag


example of how to style a hat for a wedding
Wearing a wide brim hat at my wedding


Back then, I already loved hats. I even had a small collection. It included a Tirolean red piece with feathers, a red pom-pom style, a pom-pom style with a long tail that one could wrap around the neck, an orange beret, a straw- and a wide brim yellow hat. I have loved hats so much that I also wore one to my wedding (photo above).


style blogger looking stylish with a boiled wool fedora
Front view of look described below


over 50 years old fashion blogger wearing a Tirolean felt hat with blanket scarf
Outerwear with Bavarian hat: Boiled wool felt fedora with plaid cape, Vittoria shearling coat, GNW tights, Harley Davidson booties, LeatherCoatEtc gloves, and Philip Lim 3.1 bag


woman looking stylish with hat and leather coat
Hat with zipper flower, cayenne boxy leather coat, Covington ankle strap pumps, unbranded pantyhose, unbranded printed scarf and Modalu Pippa bag


How to Look Stylish with Hats Today

It has been a while that hats were in fashion. However, hats are a hot trend right now. Here are some tips how to wear a hat that is not a baseball cap, sunhat on vacation or cowboy hat when visiting a western bar.


mature woman drinking champagne and eating on a deck wearing a hat and pearls
Liz Claiborne hat, T-shirt, Jord bamboo men’s watch, three strands pearl necklace, Akoya pearl necklace c/o The Pearl Source Inc., and sunglasses c/o Winkwood


Best Styling over 40

As with all trends that we see around for a second time, we have to make sure to style the trend modern. When we style a trend like it was styled the first time around, we are at risk to look Old Lady or (even worse) like wearing a costume. Here are examples how to style the hat trend in midlife to achieve an effortlessly chic look.



midlife woman in winter outerwear with a chic hat
Thrift store finds hat and collar, shearling coat, statement belt, Burberry bag, lew morgano suede pants, Clarks booties, and LeatherCoatEtc gloves



style blogger in winter coat, sheath dress, boots and hat with wooden bag and gloves
Calvin Klein sheath dress, smoky quartz necklace, Judith Leiber belt, GNW tight, Vince Camuto suede boots with chain detail, striped coat, pearl studs, LeatherCoatsEtc gloves, Timmy Woods wood bag (all own) and Scala Fabia wool felt hat c/o Tenth Street Hats


Stylish winter look with cap
Short shearling styled with Salvatore Ferragamo convertible belt, DIY cable-knit scarf (gift from a girl friend), London boyfriend jeans, Modalu Pippa bag, gray hat, and Harley Davidson booties


style book author in posh winter outerwear
Walrus wool felt cloche c/o Fashionable Hats, fitted down coat c/o Happy Goat Lucky with own LeatherCoatEtc gloves, unbranded structured work tote, DIY dress, quartz earrings, and L.K. Bennett tall suede boots


As the above examples show the head gear and outerwear look must be styled and coordinated to tie the look together. For example, in the first photo, all colors are repeated at least once in the outfit; the beret repeats the winter white color of the bag. In the look with red pants, the hat’s color is repeated by the belt, collar, and bag; the print of the bag ties the colors of the outfit together. In the example with the Russian hat, some of its colors are repeated by the scarf, bag, and coat. The look with the pea coat is an evergreen. See this guide how to style your outerwear.


Which Hat to Wear with Which Clothes

  • Wide brim hats like in the wedding photo look great with Euro Chic outfits like fitted sleek dresses, or skirt suits. Think Princess Diana, Kate Middleton.
  • Floppy wide brim hats work well with modern Bohemian Style outfits.
  • Visor caps look great with casual outfits. They look more posh than a simple baseball cap.
  • Russian style head gears need faux fur coats, heavy wool coats in ageless military style, and shearling coats. Adding a large Russian or plaid scarf can provide an extra layer of insulation. Belting the scarf ups the style factor, adds shape, and looks posh.
  • Straw hats are for summer. Wide brim, non-floppy straw hats look great with sleek maxi dresses that lack a Bohemian vibe. Adding a matching scarf as a hat band makes the hat more versatile.
  • A floppy straw piece is perfect with Bohemian maxi dresses.
  • A narrow brim straw head topper is a great addition to an urban safari style look. Be careful when adding animal print to this look. Doing so can easily end up in costumery territory. It is a slim balance between looking effortlessly stylish and like trying too hard.
  • Western hats look great with an American Classic Wild West inspired Ralph Lauren like style. Stay away from adding cowboy boots plus plaid shirt and matching jewelry on all burners to avoid looking costumery.
  • Felt fedoras look great with classic trench coats, winter wool coats, and motorcycle jackets.
  • Style straw fedoras with straight jeans and a white short-sleeve shirt in summer. White denim pants or chinos with a dark short-sleeve shirt are great options too.
  • Pom-pom hats have a casual vibe. They are great with casual or sporty outdoor winter clothes like down-jackets, down-coats, pea-coats and short shearling jackets. In the urban jungle, they also look trendy with heavy camel coats or wool coats as well as Duffel coats. Neutral colors like black, gray and white look mature. Go for a pop of color when you are a gray fox. In all cases, skip anything neon.
  • A Greek fisherman’s hat or Prinz Heinrich Mütze as it is called in Germany, is tricky. In middle Europe, this type of cap is worn in navy blue mostly by men in fall with a straight jacket in coastal regions. On the contrary, in the US, it is a style statement worn out of its original content. Like Isaac Mirzahi once said one has to try out various pieces and looks. Then you wear what looks the rightest wrong.
  • Trapper hats look great with shearling coats, down coats or heavy wool military-style coats.



Further Inspirations with how to Look Stylish with Hats

Don’t let the right outfit be a random thing. Wear the right look in every situation by looking up what to wear when in How to Dress for Success in Midlife. Buy the book now.


Alaskan fashion blogger in street style
Back view of outfit with Levis denim jacket, Oliveo leather skirt, Prada bag, zipper flower decorated fedora, and Valentino pumps


midlife woman wearing Fairbanks street style
Close-up on outfit with Oliveo leather skirt with Kirklander sweater, Levis denim jacket, Festina watch, Prada bag, and Valentino studs


stylist showing what to wear in the first weeks on a new job
Burberry motorcycle coat with GNW tights, 3.1 Phillip Lim bag, booties and hat


stylist with tunic dress, scarf, sun protective headgear as an example how to look stylish with hats
Scarf, dress tunic and sun protective headgear c/o Coolibar, sunglasses c/o Eagle Eyes, own Hermes collier de chien belt, Nine West pumps


style blogger in black with leopard print dress, coin belt, hat and wedges at Pike's
DvF silk wrap dress, Aigner wedge sandals, coin necklace worn as belt, lace camisole c/o Cami Confidential and hat c/o Tenth Street


How to Wear Vintage Styles

Pill box styles are great vintage finds when you can pull the style off (see the outfits below). The one in the next photo is even older than the jacket and looks quite Russian. Maybe it is even from Russia given the high Russian immigrant population in Interior Alaska.

Maybe it is this hat, why many people think I am from Russia when I make them guess. 😉

stylist with Russian pill box
Leopard diamond jacket with Eli Tahari leather dress, Dior over-the-knee boots, Kate Moss for Longchamp bag, leather gloves, pill box hat


over 50 years old stylist in blue burgundy autumn look with jacket and pill box
Pea jacket c/o London Traditions, vintage pill box, Pendleton plaid wool skirt, twigg’s pantyhose, Ivanka Trump heels


dancer with 1920s flapper sequin cap in lace and chiffon performance dress
Unbranded fishnet tight, Very Fine Dancesport Shoes sandals, 1920s sequin flapper cap, Swarovski crystal earrings, necklace c/o Happiness Boutique  and dress c/o JJ’s House


Pom Pom Hats Ideas

 style blogger Nicole in outerwear with a shearling coat, scarf, and pom pom hat
Shearling coat with chevron scarf, pom-pom hat, Harley Davidson booties, Philip Lim 3.1 bag, LeatherCoatEtc leather gloves,  and tight c/o Hanes


influencer showing how to look stylish with hats wearing a pompom beanie
Loft jeans, LeatherCoatsEtc red pea coat styled with a pom-pom hat for a posh casual outerwear look in winter


Photos: G. Kramm

© 2013-2022 Nicole Mölders | All rights reserved

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This Post Has 2 Comments

  1. Michelle Churchman

    Really fun post, Nicole! Since I met my husband 4 years ago, I am learning to wear hats for the first time in my life, because he has rather extensive hat collection.