Ultimate guide to look incredibly stylish with hats
Zoom-in on fedora with zipper flower
  1. How to wear hats of the past
    • Headgear when I was a kid
  2. How to wear hats today
    • Best styling over 40
  3. Which hat to wear with which clothes
    • Further inspirations with hats
    • How to wear vintage styles

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Hat trends of the past

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 perenially. They were a big do in the first half of the last century and 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.

Headgear 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. My mom had a beautiful gray hat with feathers that I adored. My late 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.

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

Back then I already loved hats and 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 donning a boiled wool fedora

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 (all own)

How to wear hats today

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

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.

mature woman in winter look with beret Winter outerwear outfit with beret, scarf, ethnic belt for shape, shearling coat, shearling booties, GNW polka dot tight, and statement bag (all own).
midlife woman in winter outerwear with a chic hat Thriftstore finds hat and collar, shearling coat, statement belt, Burberry bag, lew morgano suede pants, Clarks booties, and LeatherCoatEtc gloves (all own)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
#over40fashion posh winter outerwear with Russian hatRussian hat, shearling coat, Modalo Pippa bag, London Jean boyfriend jeans, DIY cable knit scarf, Salvadore Ferragamo belt, and Harley Davidson booties (all own)
mature woman with pompom hat Loft jeans, LeatherCoatsEtc classic red pea coat styled with a pom-pom hat for a posh casual outerwear look in winter (all own)style book author in posh winter outerwear Walrus wool felt cloche c/o Fashionable Hats, fitted downcoat c/o Happy Goat Lucky with own LeatherCoatEtc gloves, unbranded structured work tote, DIY dress, quarz earrings, and L.K. Bennett tall suede boots

Like these outfit ideas? If so, please feel free to pin them to your own Pinterest board so your family and friends can see them too.

As the above examples show the hat 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.

Which hat to wear with which clothes

  • Wide brim hats like in the wedding photo look great with Euro Chic looks like fitted sleek dresses, or skirt suits.
  • Floppy wide brim hats work well with modern Bohemian outfits.
  • Visor hats look great with casual outfits and look more posh than a baseball cap.
  • Russian style hats need faux fur coats, heavy wool coats in military style, and shearling coats. Adding a large Russian scarf or a 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, not floppy straw hats look great with sleek maxi dresses that lack a Bohemian Style vibe. Adding a matching scarf as a hat band makes the hat more versatile.
  • A floppy straw hat is perfect with Bohemian maxi dresses.
  • A narrow brim straw hat is a great addition to an urban safari style look. Be careful when adding animal print to this look as you can easily end up in costumy territory. It is a slim balance between looking effortlessly stylish and like trying to hard.
  • Western hats look great with an American West Ralph Lauren like style. Stay away from adding cowboy boots plus plaid shirt and matching jewelry on all burners to avoid looking costumy.
  • 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 pea-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 on anything neon.
  • A Greek fisherman’s hat or Prinz Heinrichmütze 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. In the US, it is a style statement worn out of its original content. In the sense of Isaac Mirzahi, one tries out various pieces and looks what looks the rightest wrong. See photo in the outfit inspirations below.
  • Trapper hats look great with shearling coats, down coats or heavy wool military style coats.

Further inspirations 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.

midlife blogger with motorcycle coat and fedora Burberry motorcycle coat, GNW tight, 3.1 Philip Lim tote, zipper blossom embellished fedora (all own)
style blogger looking effortlessly chic with a drivers cap Drivers wool cap, Great Northwest denim jacket, Newport News leather pants, Ralph Lauren pumps, Kieselstein Cord belt, Jeanne and Pierre sweater, pearl necklace (all own)

mature woman in summer dress with straw hat Straw hat, Coach bag, Juicy Couture patent leather mules (all own), and summer vacation dress c/o HSN

stylist with tunic dress, scarf, sunprotective headgear Scarf, dress tunic and sun protective headgear c/o Coolibar, sunglasses c/o Eagle Eyes, own Hermes collier de chien belt, Nine West pumps

olders lady in Casual Friday outfit with high waist pants, cropped jacket and fedora Fedora c/o Tenth Street, own Tee, cropped Star denim jacket, Gucci suede belt, Prada bag, Anne Klein open-toe pumps, Festina watch, Hermes collier de chien bangle, and lew magram high waist pants

#fashionover40 hat matched to outfit by means of a scarf Metal bag, gold sandals, Chica sundress with scarf used to update a straw hat (all own)
#fashionover50 casual weekend look with straw visor Oliveo leather shorts, Michael Kors paten leather plateau sandals, Carhartt gingham shirt, Kieselstein Cord belt, Hermes bangles, Tissot watch and  straw visor (all own)
style book author with Greek fishermen's cap Jones New York cardigan, Ralph Lauren polka dot skirt, The Limited polo shirt, Hermes collier de chien bangle, Kieselstein Cord belt, and LeatherCoatsEtc. Greek Fisherman hat (all own)

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 (all own), lace camisole c/o Cami Confidential and hat c/o Tenth Street

over 50 years old woman in fashion week inspired fall style with biker jacket, scarf, head topper, jeans and sandals Vienna Scala hat c/o Tenth Street styled with own James & Graham biker jacket, wrapped twice knotted Oscar de la Rente scarf, Loft sweater, Oliveo Italian style jeans, Nicole plateau high heel sandals, and Celine shopper

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. May be it is even from Russia given the high Russian immigrant population in Interior Alaska. May be it is this hat, why many people think I am from Russia when I make them guess. 😉

over 50 years old Alaskan blogger in classic winter outfit with 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 (all own)
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 (all own)
dancer with 1920s sequin cap in lace and chiffon performance dress
Unbranded fishnet tight, Very Fine Dancesport Shoes sandals, 1920s sequin cap, Swarovski crystal earrings (all own), necklace c/o Happiness Boutique  and dress c/o JJ’s House

When you found these tips helpful tweet your friends
See this ultimate guide on how to wear hats. #NationalHatsDay Click To Tweet Thanks <3

Will you jump the bandwagon on the hat trend? If so what kind of hats do you want to try out? How will you style them? Have you already a hat? Do you like the hat trend? Let me know your style challenges with hats so I can help you with tips and tricks.

When you like the blog, you may also want to get my style recipe book How to Dress for Success in Midlife.  Buy it now.

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Photos: G. Kramm

© 2013-2020 Nicole Mölders | All rights reserved

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.


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