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  • Writer's pictureWhitney Wisdom

How to Select Boots that will Never go out of Style


Some boots work for just an outfit or two, some boots you can marry. Here's the difference.

The.Hottest.Boot. is named about this time every year and it is usually starkly different from the previous year's. Keeping up with boot trends is crazy expensive so I try to find ones that will make me look like an “it girl” for many seasons, not just one. Here are a few insider trading tips on picking boots that will remain on trend for 5+ years.


Length: When people say “Mid” I can’t help but think of fashion. Specifically midi skirts and boots. Mid is the most sure thing. There are many psych theories about people consistently gravitating towards the middle option. (Most of which I learned about in Marketing Research.) You know how people say when in doubt choose C? That’s classic mid. Boots that hit mid calf will always have more longevity to them than thigh high styles and ankle booties.


Two tone boots are the best way to dip your toes into the mix match shoe trend.

Style: Ultra unique boots that are ahead of the mass market curve, will eventually fall inline with everyone else. I am picturing that bell curve from Econ. Try to buy in that early adopters category to get the most bang for your buck on your buys plus, we all secretly love saying “I told ya so.” I got these gray suede, no heel, over the knee boots in 5th grade. It was a love at first sight moment. I had seen them in some fashion mags and nowhere else until 8th/9th grade when my whole school had them too. I got three extra years of stomping around in my thigh highs before they fell off the face of the Earth.


But maybe, you’re just a regular person not on a quest to start your own trends and spend your time obsessing over hobbies that aren’t fashion-related. That’s cool too. I am here to tell you: avoid novelty. When looking for your forever boots know the crazier trends die the quickest deaths. Glam cowboy boots worn for non-rodeo activity, platforms designed with David Bowie and Elton John in mind, are boots you date, not marry. Go for boot styles that are in repeated history like a military inspired combat boot, a Victorian lace up, riding boots (Hi, yes, riding boots have just resurfaced.) a slim leather or nylon sock boot that hugs the leg.


Toe Shape: I don’t have a lot of commentary on toe shape as I think this falls under the overarching style of the boot but it does come up in boot conversation very often. The bottom line is this: square toes (ladylike), round toe (grunge), pointed toe (fancy), are all killer in different styles of boots. Toe shape on its own, is never something that will make a boot in or out.


A ladylike square toe is essential to my personal brand.

Sole: The ideal sole style of a boot is one of the last things to change. In about 2020 we saw a shift into platform and overly thick chunky soles breakthrough mass markets. This makes sense as 2020 was a year of change. Rugged boot bottoms will likely be a thing for the next five or so years so go ahead and invest in those Doc dupes you’ve been eyeing.


The other thing to look at when sole searching is comfort. Soles that are not completely flat, with some padding and arch support are best. Rubber soles help decrease slipping. Other than that, in terms of sole styling we pretty much have thick and thin. Thick soles are durable and are having more than a fleeting moment.


Texture: Texture gives your boots a clothing-like dimension.Texture adds feeling and feeling is life. Something with a raised edge makes your boots pop! Geometric shapes and raised animal prints like croc in solid colors will always be it.


Zippers: Unexpected details win year after year as well. Zippers are a functional detail that allow us to get in and out of most of our boots. Over the years we sway from zippers hidden under fabric, dyed to match zippers, and noticeable zippers, usually silver. Today we want to draw attention to those special details. Zippers that crisscross in fun neons on a black patent leather midi boot are a trend-fresh option. Which brings me to everyone’s favorite fashion topic: color.


These boots play peek-a-boo!

Color: Typically for boots that live a long life I recommend your neutrals. Black, white, and every iteration of brown. White was not always considered a core color for footwear due to the dirtiness factor. White has been everywhere the past few seasons as this principal has just been debunked. (Fashion rules at large, last way longer than they should.) The color will outlive the disco cowgirl craze. Furthermore, like Taylor Swift and Joe Alwyn, white boots are in it for the long haul. Back in Wedding Szn we saw skin color heels as the preferred pick to really highlight our dresses and jumpsuits because it is a genius way to add extra height. Boots in a hue a shade or two darker than your skin tone - just enough to stand out are ones you will wear your entire life. They can be worn with your sweater collection, all the flannels, and every skirt you’ve ever laid eyes on. A few weeks ago I wrote about Unexpected Essentials Flesh colored boots are the exact opposite. You expect them to be ye ole faithful and they are.


Hot punchy pinks and limes just broke onto the scene so we are in a good spot now in terms of fierce color trends however, unless you keep close tabs on runway shows and street style I would advise against going for boots in a color that is merely of the moment. If you are in the market for a unique colored boot I select the color you love wearing the most, the one that will match back to your arsenal of clothing and accessories the best. For me, I can make any shade of pink work, anytime of year. For you, maybe that’s a less loud maroon or a cool blue. It is times like these when falling back on your personal style feels most natural.


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Frieda Holland
Frieda Holland
25 okt. 2022

You sure have an eye and a gift for fashion. I love your blog. It really helps others to join. You out of the box. You will go far, as you continue to pursue fashion!

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