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How to Wear Chunky Block Heel Boots, Sandals, Shoes & All That

Chunky block heels are still strong for fall 2015, winter spring 2016

by Tina Boomerina (Christina Gregoire)

I’m not young. I’m not tall. I’m not skinny. But, I can fake this stuff with high heels. Unfortunately, I am no longer steady in stilettos. So what’s the answer? Shoes, sandals, boots, and ankle booties with chunky heels. Yep, fat block heels give you and me more stability than skinny heels do, because this style of shoe has more to deliver where the rubber meets the road.

read about how to wear chunky block heels

Chunky Heel Winter Boots

I don't want to give you the impression that all chunky heels are high. Some block heels are short and stocky... and about as high as kitten heels. Those low, square heels are nicey-nice, but I like to wear the towering-inferno versions, the geriatric-Elton-John styles.

Well, geriatric is not the right word.

I just threw that out there for a laugh from all you post-disco chicks who remember seeing Sir Elton John in his glittery 70s garb, with shiny bomber jackets, rhinestone sunglasses, and sky-high platform boots. Hello Yellow Brick Road.

High Heels Rock

I love high heels. However, I must confess that I don’t really wear shoes that are as towering as a disco inferno, although I do wear heels almost everywhere I go. Hey, I have to wear flats when I'm going to the dog park or when I'm playing tourist, but the rest of the time, I add a few extra inches to my height.

I feel better when I'm taller. I don't care that my feet are going to suffer... I'm terribly vain. What can I do?

What Do You Wear With Chunky Heel Boots and Shoes?

What are the best things to wear with chunky heeled boots or booties or pumps or sandals. The answer is "almost anything". You knew this was a trick question, but I didn’t fool you.

The only trick is that you must match the feel of your block heel shoe with the feel of your outfit.

I suppose there are a few things you can't wear chunky boots with... like a swimsuit. (Try that and you'll end up looking like a hooker in kinky boots.) However, chunky heels go with almost everything else... jeans, trousers, day dresses, maxi skirts, party dresses... and... there must be other things that go with chunky heel shoes but I'm drawing a blank... Oh. Champagne. You can drink champagne out of block heel slippers.

Shoes With Block Heels: Dressy or Casual?

Some block heels are casual, some are prissy, some are masculine, some are summery, some are wintery, some are ornate, some are glittery, some are meant to be evening wear… etc. It’s hard to explain. You need to find the footwear that matches the gestalt of the outfit.

What I mean is I think you probably should consider the formality of the outfit more than the color you're wearing. However, there are times when you should go just the opposite of whatever shoe is expected. Mix it up. Have a little fun. Play fashion roulette.

read how to wear chunky heels

Wide Chunky Block Heels

Wide Block Heel Shoes and Boots

Most wide (thick) block heels are meant for casual outfits, but you can skirt the issue every now and then... hahaha.

See the photo above for outfits that show a few ways to wear wide, extra-thick block heels:

  • Thick Chunky Heel Sandals: Check out this party-girl outfit with the pink faux fur from Dorthy Perkins. (Does this have a disco feel or what?) This photo certainly proves you can wear fat block heel sandals with skinny jeans... even in winter. And, you're less likely to slip and and slide and break your ass because you'll get better traction with those extra square inches touching the ground.
  • Chunky Heel Knee Boots: This outfit shows a great cold-weather look from La Redoute. I love that navy sweater dress with the cognac brown boots... or whatever color those are. This look is great for travel. It's great for work. You can wear this anywhere... except the beach.
  • Ankle Boots With Block Heel: This House of  Fraser outfit can go from work to after hours without a change. The booties give a tough-girl edge to that girly floral dress.
  • Wide Heel Boots and Leggings: This outfit from La Redoute shows how good you can look when you pair some chunky heeled boots with a fall sweater and leggings...  and you tuck your leggings into the boot. What a perfect winter style.
read about chunky heels

Chunky Heeled Party Shoes

High Heeled Chunky Shoes for Parties:

Okay, kids. We all know how good chunky boots look with casual outfits, but what about party clothes?

Well, there are lots of groovy options for those of you who want to go tall without losing your balance. And all of those options have a thick, chunky heel.  (I am truly a bit more wobbly than I used to be, but I refuse to give up and wear old-lady shoes. And, as much as I like stilettos, a walking cast is not my best look.)

Another cool thing about block heels is that the larger heel often becomes a canvas... a perfect place for adding embellishments. Look for stores that carry heels covered in gold, silver, rhinestones, or glitter. High heels never looked so good.

So, now you understand that block heels can add an extra element of glamour to an outfit, but are these shoes something that was invented to protect little old wobbly ladies from falling?

Hahaha. No. This look was started by the young and the trendy. That's why these shoes, with their fat heels, are so cool.

These high heels are like "mom stilettos" for women over 40 or 50. They are perfectomundo for hipster mothers who have to chase down their kids at weddings. They are fabulisimo for sexy grandmothers who want to look a bit less obsolete and dowdy, while staying upright as their cruise ships rock and roll on the open seas.

read about hip footwear trends

Chunky Heel Sandals

Thick Block Heels Are Hip and Edgy

Fat, chunky heels are also a great way to keep an outfit from looking too girly, precious, prissy, sweet… or ________ fill in the blank with your own word. Block heels are a rocker-chic look.

Check out the cute hipster party outfits above to see the latest fashions for trendy London teens and twenty-somethings from Miss  Selfridge. Skirts and dresses are somewhat rare on kids these days, but I have a feeling these pictures will help bring flirty dresses back. Oh... if only I were 15 and living in the 70s... in a parallel universe with the internet. Those British outfits would be mine.

Well, if you are over 40, I'm not telling you to wear socks and platform sandals. If you look like Betsey Freaking Johnson, go ahead, but for the rest of you, I'm only showing you these outfits so you will understand how big block heels are going to be.

She's got electric boots... a mohair suit...

Chunky heel boots and sandals are hip and edgy... and fun... and perfect for me. Thank you, God. You've made me taller for another year.

More Articles for Hip and Edgy Women of a Certain Age:

Fashion Boots for Women Over 40, 50, 60: You Can Never Have too Many Boots

What Are the Best Wide Calf Boots for Women?

Best Jeans: 5 Denim Trends for Fall and Winter

How to Wear Leggings if You're Over 40, 50, 60

how to wear boots shoes chunky heels

Main Photo

Photo Credits: prshots.com.

  • Main Photo: Orange rust Sandals River Island, booties Long Tall Sally, both 2016.
  • Chunky Heel Winter Boots: Dunnes Stores.
  • Wide Chunky Block Heels: Dorohy Perkins, La Redoute, House  of Fraser, La Redoute Plus Size.
  • Chunky Heeled Party Shoes: Dorothy  Perkins photo but shoes at Asos (clockwise) M amd S, New Look, Dune, New Look.
  • Chunky Heel Sandals: Miss  Selfridge.

What do you think of this article? Women over 50 are not ready to give... kookookachoo Mrs. Robinson, leave a comment at the bottom of the page.

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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  1. Elise

    The shoes shown look great in the pictures - very stylish. I'm definitely going to be on the lookout for some chunky heels. My feet will thank me!

    • Tina-Boomerina

      when you're out walking on a slippery frosty sidewalk, your butt will thank you... because you won't be falling on it.

      If you live in Hawaii, forget that.

      You sound younger than I (from your name), so you might still be able to do stilettos, but you will be waaaaaaaaaaaaaay more stable in chunky, block heels. The really fat heels (bigger than the ones on this page) are super trendy, too.

      Block heels are great for dancing, etc.


  2. Rita

    These chunky heels are nice looking. However, some of them are really tall.

    High heels are harmful to your feet. I've written about it several times on my blogs for consumers.

    Rita, consumer journalist, blogging at The Survive and Thrive Boomer Guide

    • Tina-Boomerina


      You're right. I know in my heart you're right... but I just can't break my habit.

      God made a tiny mistake when he forgot to add 3 and 1/2 to 4 inches to my height. It's just that I look so much better with heels. I wear (semi) flats when I'm walking around all day on cobblestones... or when I'm going to the dog park. And, I doubt I would toddle around in heels if I worked retail, but people seem to treat me better when I'm "tall".

      I would never suggest that other women wreck their feet by wearing towering chunky heels, but I'd rather live fast and die young... What? You say I'm 62 years old? How did that happen... I guess I'll just live fast and die old.

      You are absolutely right Rita, but I'm stubborn and vain.


  3. jay

    I like wearing block high heel boots. looks very cute with tights and mini skirts or leggings. wear with print leggings too