5 Classic Boots to Wear For Easy Modern Outfits

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Classic boots can be defined as a style of boot that never ages. Seriously, think the classic Chelsea boot. It never goes out of Vogue and you never have to replace it. You can wear these classic style boots with just about any outfit from work to play for a modern day look. Here’s the list!

What Are Classic Boots

Boot styles that never age, the design usually has a history behind it and generations have spent countless years styling and perfecting these classic styles.

Here were some common questions when it comes to buying classic boots:

  • Considering a new designer pair
  • Doc Martens!
  • Something in the middle, good quality and moderately priced
  • Getting some repaired
  • If I have a gap to fill ill invest
  • Shoes are the thing I need the least right now
  • Rewear!
  • New investment
  • I need options!
  • Saving my pennies

RELATED: Styling Winter Boots and Sustainability

Which Boots Are In Trend?

This of course changes every year but let’s try to stick with the classics here, that way you’ll shop less and love what you own more.

What Are Classic Chelsea Boots

Classic Chelsea boots are a style worn since basically the beginning of time. They hit just above the ankle, have elastic side panels for added comfort and have a low heel. The style is reminiscent of menswear but for anyone.

Chelsea boots should always been in your rotation every year, the wear you can get out of them is unmatched. Think dresses, denim, skirts, dress pants. The options are endless which makes them worth investing in.

Classic Boot Styles: Best Boots For Fall

A few classic styles and the best boots to wear for fall. I wear a rotation of these styles every year, they are easy enough to pair with just about anything, a classic pointed toe or an ankle boot are two great options that never go out of style so you can shop less.

The Classic Chelsea Boot

A great option to have year round, they’re muted enough to be a great casual daytime boot, and fit in perfectly if you plan on participating in fall activities. I tend to own more fashion boots because of my lifestyle, and one pair of hiking/messy boot. So it depends on what your day to day looks like.

Blundstone Original Chelsea Boot. Either black or brown these are the epitome of comfort, practicality, longevity and are cute to boot. They’ve been on my wish list for quite some time, they’re not cheap but you really do need a good colder weather boot you aren’t afraid to get dirty.

The Classic Ankle Boot

I love a classic ankle boot, all year it doesn’t matter. They polish up a look and elevate any casual outfit, the pop of bright white at the bottom adds a nice contrast especially in the cooler months when people tend to wear a lot of black.

I’ve linked a few pairs down below that were popular last year and still hold merit.

Fall Riding Boots

Riding boots give a really beautiful heritage feel, pair them with a dress pant or great pair of denim and you’ll feel modern without trying too hard.

The Combat Boot

Doc Martens for me are the classic cold weather boot. I have the Arcadia Chelsea boot and love them, they’re different with a hint of cherry red. They look great with denim and the quality is outstanding. My wish list does consist of lace up Doc Martens though for a well rounded black boot collection. You just can’t beat the quality and they never go out of style.

If I go hiking in the Fall I wear my Doc Martens. They’re incredibly comfortable, these are basically my go-to boot for getting dirty as well. A great all purpose running errands and doing messy kinda stuff boots.

Tall Boots for Fall

Another great style of classic boots are tall boots, this style is great for fall because you can pair them with shorts, skirts and dresses.

Autumn Boots and Styling

Style ankle and combat boots with cropped denim, a button up or a sweater. Riding boots and tall boots look great with a dress, skirt, or trousers tucked in with a layered or oversized top. Chelsea boots can really be own with anything just keep your denim length in mind.

Overall, have fun with your outfits while styling these 5 classic boots for fall!

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