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7 Fall Boot Trends 2015: Hip Footwear to Wear and to Avoid

great boot trends for fall that you can wear

by Tina Boomerina (Christina Gregoire)

It's time to call the contractor and have more shelves put in your closet, because it's boot shopping season. Footwear is probably the easiest way to update your otherwise pedestrian wardrobe. And, no matter what size you are in clothing, you can almost always find something cute that fits your feet. So, onward to knee boots, over-the-knee boots, booties and possibly a shoe or two for fall and winter 2015-2016.

read about boot trends

Fashion Boots 70s Style

This season, there are boots to love, boots to make you happy, and boots that make you go hmmm...

However, I love writing about shoes and bags and other groovy stuff that comes in my size (joke). Maybe I should do more articles about accessories.

Look for Boots and Booties That Aren't Crazy:

I went through a whole bunch of fashion websites, so you don’t have to. If you really like wading through stuttering slideshows, annoying popups, and frequent crashes to see all the haute couture boots that you can't afford and wouldn't wear, knock yourself out. I'll put Pinterest links in the appropriate places.

However, if you want basic trendy footwear, I'll show you examples of boots that are similar to what you can find in stores like Nordstrom, Macy's, and discount stores. Hey, if you want to spend three thousand on a pair of boots... you can do that. I wouldn't. I would buy cheaper knockoffs or look for something similar in a consignment store.

Do You Really Need a New Pair of Boots?

Why, exactly, do we always want to buy more shoes? We can only wear one pair at a time.

I suppose we want to fit in. Or else we want to stand out. Or stand above... yet... still WITH the others. Fashion is a bit of a social game. But, a pleasant one.

Best Boots and Booties for Fall:

So, which boot styles are cute and chic and wearable? Well, it depends on your age, your feet, and your balance. I just wore a pair of high, flatform Kork-Ease sandals and had no problem balancing on them while walking around the big city (wink wink) of Bend, Oregon... and I'm no spring chicken. However, there are a lot of younger chicks who won't wear anything that takes them off the ground. So, it's up to you to choose the footwear that makes you comfortable in your own way.

Me? I'm vain. I like to look taller. I wear all kinds of silly shoes that trick the eye into showing you a somewhat height-weight-proportional version of myself... if you know what I mean?

My best boots have a bit of a heel. However, I also wear boots that are absolutely flat when I need to cover a lot of ground (or when there's ice on the ground). I also have a special selection of "nonsense footwear" that I wear for no other reason than to make myself happy.

Do You Want Functionality or Cuteness?

read what to wear and what not to wear this fall

Perfect Boots for Women Over 50

Whenever you buy a pair of shoes or boots, you have to weigh vanity against practicality and come up with your own ratio of "cuteness" versus "functionality". All of us do that. It's a secret, calculus-based formula, which women have sworn never to reveal to men.


  • The Man: "Honey, why are you wearing those high heels to go hiking in the mountains?"
  • The Woman: "Sweetie, these boots aren't high at all. They're just flatforms with a bit of a wedge."
  • The Man: "Huh?"
  • The Woman (thinks to herself): "I would love to wear flat comfortable shoes, but I HAVE to wear heels because I've gained 20 pounds and someone might post my photo on Facebook. If I add an extra 3.25 inches to my height, I will look like I've only gained about...." Woman runs for calculator.
  • The Man (thinks to himself): "Oh my God, women are crazy. I'm turning gay."

Fall Boot Trends for Real Women:

Well, no one can tell a smart, independent woman (like you) what the best boots are FOR HER (for you), but writers (like me) can definitely give examples of what the fashion-design elite are showing on the catwalk. And, YOU can decide which boot trends will make it into your own closet... and which boot trends will be kicked to the curb.

So, let's discuss a few of the boot trends. And, you can tell me if you think these boots are cute or if you think they'll push unsuspecting women towards fashion victimhood.

The following trends are listed in no particular order...

read about new boot trends for fall

Ankle Boots With Cut Outs

1. Boots With Peep Toes and Cut Outs:

Boots with cut outs (holes that let the rain and snow in) fall somewhere in the "chic nonsense" category. They don't do what boots are SUPPOSED to do, like protect your feet from cold... but that's what makes them so weirdly fun... in a Versailles courtier way. I mean... you're wearing these crazy boots because everyone at court is. Oh, nevermind.

But, peep-toe boots and booties with missing pieces are super on-trend AND they will make anything in your closet look hip and "up to date". Hey, these boots might even make YOU look hip and "up to date".

Anyway, I LIKE those boots with the cut outs. It means I'll have to get a pedicure in the middle of winter. Bummer. But, what do you think?

read how to wear OTK boots if you're a woman over 40 50... and see trends

Can Women Over 40 50 Wear Over the Knee Boots?

2. Over-the-Knee and Thigh-High Boots for Women Over 50:

Oh... what am I going to tell you?

I like the look of OTK boots, but you're not going to see me walking around in them. I'm pretty sure age 62 is too old for this look. I may change my mind over time, as over-the-knee boots become more "main street", but I'm not going to run out and buy a pair of thigh-high boots today. However, YOU might look smashing in them.

Thigh Boot Rules for Women Over 40 or 50:

If you're a fashion-forward chick, and you're no longer in your 20s, I'll tell you how to wear tall boots without looking all slutsville. Use the photo directly above for reference:

  • 1. If you're over 40, you should never wear over-the-knee boots with a lot of exposed skin. Doing so is almost the equivalent of wearing thigh-high stockings and and a garter belt out in public. What you wear in your own bedroom is up to you, but you're not Cher.
  • 2. If you're over 40, you can wear over-the-knee boots over jeans and other form-fitting pants... as long as the boots have flat or chunky heels.
  • 3. If you're over 40, you can wear over-the-knee boots if your outfit is conservative and doesn't show much skin.
  • 4. If you're over 40, you can wear over-the-knee boots with a bit of bare thigh as long as you're well-covered elsewhere... but use discretion.

In reality, you can wear over-the-knee boots when you're older, but most women won't.

cute new fashion boots

Lace Up Boots for Women

3. Lace-Up Boots and Booties:

Lace-up boots are cute and trendy. I wore knee boots with this type of open lacing in the 70s, but my boots laced up the sides rather than the front. I loved my open-laced boots and wore them everywhere. This type of laced boot has a sexy vibe, with undertones of S&M, but wearing high heels for long periods of time is somewhat masochistic anyway. However, as cheeky as this footwear is, it doesn't show anything.

I'm wondering what you think of this open-lace look. Can a woman over 50 get away with these boots? I say, "Yes."

However, most of us should look for something with a flat or chunky heel. (I realize that losing the stiletto will take some of the sex appeal out of the shoe, but so will a cast and a pair of crutches.) And, since lace-up boots impart their own subtle sexuality, you should wear them with conservative outfits during the day. I like open-lace boots with long, full midi skirts. That's how we wore this boot in the 70s. (OK, we also wore this type of lace-up boot with suede hot pants, but I'm trying to purge that image from my memory.)

cool boots for fall

Patchwork & Two Tone Boots

4. Patchwork and Two Tone Boots:

I love the new patchwork boots. Unfortunately for me, I just recycled my old patchwork boots (from the 90s) when I streamlined my closet (to sell my house and move). Well, my loss is some hipster's gain, so if you live near the Goodwill in Bellevue, Washington, look for some brown size 7.5 patchwork boots. They were so comfortable... I should have kept them.

The patchwork boot is, ultimately, the most wearable trend of the year. You can take two-tone (or multi-tone) boots into the mod color-block zone. You can take suede or lizard patchwork knee boots into the groovy-70s boho zone. You can do all kinds of things with these boots, depending how you wear them.

Some patchwork boots and booties are so subtle you will barely notice the subtle texture change. Other patchwork boots are wild and fabulous.

Hurrah for patchwork shoes and boots. Can I get mine back?

read about new fashion for fall

Victorian Booties for Fall

5. Victorian Boots for Fashionable Women:

I'm not sure if this boot trend is a rip-off of the Steampunk look, a nod to the eclecticism of the 70s, or a run-in with the beautiful Stevie Nicks, but Victoriana boots are coming to town near you.

Victorian boots have an interesting silhouette. Look for lace-up ankle boots with long, pointy toes to get the whole fashion-forward enchilada. The Victorian look is the reason you'll see so many long, skinny toes in the boot department this fall.

Well, I have fat peasant feet, so I don't fit into sleek-toed shoes with this design. But, if you have German peasant feet, like I do, you don't have to cut off your small toe to get your Victoriana fix. Just look for any ankle boot with a lace-up front and a kitten heel. You can take the trendiness a little further by wearing ruffly ankle socks that peek out the top.

I won't wear any shoe that doesn't have a square or rounded toe... I don't care what the latest trend is. It's important for me to tell fashion designers that I'm NOT into pain. (Okay, that's a lie. I'm willing to endure almost any shoe or boot as long as it's wide enough for my foot to slip in. I'm no Cinderella.)

Keep reading fashion tips for trendy boots on page two. I love writing about footwear so much that I've spilled over into the next page.

Note: Photo Credits on Page 2.

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. Vicki

    Love the patchwork boots, I found a gorgeous pair at my local GW that are black and orange suede, perfect for the good witch Halloween look. No to the over the knee boots but yes to luscious leather booties with a nice chunky heel... Let's be real!

  2. Diana

    i'm 60 and boots are one of my favorite things.I'm with you on most of the trends I definitely think baby boomers should leave the over the knee boots to the younger generation, not that I don' t love them but you don' t want to look lIke you're trying to hard be young.

    Finally, living in Chicago I think the cut out boots are absolutely ridiculous. You have maybe a month or so in which you can wear them. When winter hits everyone looks crazy trying to sport fashion in knee deep snow. You might get away with them during September and October, not worth the cost to me.

    The short boots with the chunky heels are my fave, and I have several tall flat boots that I love with jeans and long and short skirts.

    • Tina-Boomerina


      I think it would be hard to pull off over-the-knee boots, but I've seen a photo of Iris Apfel in them (with a long tunic) and she looked great.

      For me, I spend my money on things I can wear for the next 10 years. I'm not really sure about over-the-knee boots. If I were to buy them (and I'm not planning to), I would get something cheap. I feel the same about boots with cut-outs. I love the way they look but I would only get them if I lived in L.A. Oh heck, I just lied. I might get cut-out boots if I wanted something to wear out (for a party or a nice resto or a club).

      Yeah, like I go clubbing every day... haha.

      I think most cut-out boots are meant to be worn as an evening sandal, although your comment makes it sound like women wear them during the day.

      So........ I guess both types of boots are worn as a statement about one's income (or level of credit card debt)... as well as a fashion statement.

      If you look in my closet, I only have flat boots (not many), chunky-heeled boots, and similar styles that can be walked in. In MY shoe department, I only see chunky-heeled shoes, flat shoes (not many), and flatform sandals (flat platform sandals)... oh... and some beach slippahs. Why would I spend $800 on stilettos just to spend thousands on doctor and hospital bills? Sure, those crazy booties are cute and sexy, but bunions and casts... not so much. And, in Chicago... some of those boots put you at risk for frostbite.

      Fashion can be fun, but it can also be strange.

      Thanks for your comment, Diana.