4 Must-Have Fall Boots: Your buying guide

Boots

If there’s one thing I love about fall fashion most, its boots. They’re comfy, easy to outfit, and if you get a good pair they can last you for years. The only downside? There are so many options out there that it can be hard to decide which pairs are a good investment and exactly how many pairs you actually need. With the arrival of that little chill in the air (or is it just my A/C?) I figured now was as good a time as any to craft your fall boot shopping guide.


1. The Classic Knee-High Riding Boot
. This is a boot that never goes out of style. My recommendation? Pick a flat boot with interesting buckle details in a chestnut or taupe shade (goes with everything). If you’re willing to fork over a little extra cash for genuine suede or leather, you’ll get years of wear out of these boots.

Buy it: Nine West “Sassyfran” $179 | Pink and Pepper “Racer” $69.95 @ DSW | Style & Co. “Ryder”$69.99 @ Macy’s


2. The Dressy Knee-High.
 Black is never out of style, so that’s your best bet color-wise when choosing your knee high dressy boot. A covered wedge in leather is a perfect solution – wear it over tights with a dress for a dressier feel, or go more casual with skinny jeans, a button down blouse and your favorite fall jacket.

Buy it: Bamboo Carmela-16 Knee High Wedge Boot $39.20 @ Urbanog | Rachel Rachel Roy “Rolettah” $179 | Charlotte Russe Double Zipper Wedge Boot$42.50


3. The High-Heel Bootie. 
These booties are perfect for fall paired with ankle trousers and skinny jeans. For a wear with everything bootie go with a tan or taupe shade, a wooden heel and a lace up detail. For instant class, pair with tights, your LBD and your favorite blazer.

Buy it: DV by Dolce Vita “Joli” $118.95 @ Nordstrom | Seychelles “Fever Pitch” $139.95 @ Nordstrom | Blowfish “India”$69.95 @DSW


4. The Wild Pair. 
My fall wardrobe is always full of neutrals and muted hues, so I like to enlist the help of my shoe friends to spice up my outfits. Prints, studs and fringe are all perfect on-trend options for your wild pair.

Buy itRachel Rachel Roy “Camino” $169 | Zara Studded Cowboy Ankle Boot $129 | Nine West “Charmaine” $180

If you’re anything like me, you don’t have the funds to buy all 4, so build up your collection over time! Assess your wardrobe and think of what the best options are for you. If you’re just starting your collection (soon to be obsession), I recommend a neutral colored riding boot and a high heel ankle bootie in black. These two beauties will have you covered for any occasion.

What’s your must-have fall boot style? Do you buy new pairs each season or stick with old favorites?

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65 thoughts on “4 Must-Have Fall Boots: Your buying guide

    1. twenty-something Post author

      There are, it’s so hard to pick just a few to buy! Riding boots are a staple in my fall wardrobe so they’re a favorite of mine too, but I definitely recommend having a fun pair on hand. They’re a great way to spice up a simple outfit!

      Reply
    1. twenty-something Post author

      I definitely feel you there – the pair of riding boots pictured were $180 when I bought them last year. At the time, it was HARD to fork over that much cash for a pair of shoes, but after wearing them non stop last year and still having them be in such great condition this year, I know it was definitely worth it.

      Reply
  1. fizzandfrosting

    Riding boots are definitely better my favorite, but I’m obsessed with finding a pair of high-heeled booties for this season. I love the Dolce Vita ones you have pictured.

    Reply
  2. Rachel

    What a fun take on a fashion post, Stephanie! I have a few pairs I’ve built up over time because, like you said, they can be very expensive (I refuse to pay more than $70 on a pair!) My favorite is the riding boot style since they fit me the best.

    Reply
    1. twenty-something Post author

      Thank you Rachel! I’ve been building mine up over time as well, and last year I waited until the end of the season to buy a few because everything went on sale. Riding boots are a favorite style of mine too, definitely a fall wardrobe staple!

      Reply
    1. twenty-something Post author

      Haha, to me boot shopping is a little bit like Christmas shopping…I like to do it WAY in advance so it doesn’t seem like I’m spending all of my money at once right at the last minute. Plus I feel less guilty about spending when I spread out my purchases….:)

      Reply
    1. twenty-something Post author

      You MUST have a riding boot! Best money I’ve ever spent on shoes hands down. As for the leopard booties, the platform is nice and high so they’re surprisingly comfy. I got a gel insert for them for the balls of my feet and that helps a lot. The fact that they’re a wedge heel makes them super stable and easy to walk in – I definitely want to see yours if you buy some!

      Reply
  3. Pearls and Lace

    I always get excited for boots for fall and winter! I have a pair of knee-high black suede boots that I love to wear with tights and skinny jeans! This year I’m looking for a nice pair of brown leather riding boots to add to my boot collection! I love that you picked a leopard print pair, it’s so popular for fall!

    xo, jen

    Reply
    1. twenty-something Post author

      I love boots and fall is such a great season! Brown leather riding boots are a great choice, I’d love to see what pair you buy. And thank you – leopard print is a staple in my wardrobe so I love having a fun pair of wild shoes for fall.

      Reply
  4. Bree

    I completely, 100% agree! Especially with the one wild pair. I feel like you can really mix up the other boots – a deep cognac boot instead of a riding boot or a pair of short black boots as your dressy boots – but a pair of fun wild boots often get missed or forgotten. I think it’s because they are a bit more “wild” they aren’t seen as an essential – but they really are!

    Reply
    1. twenty-something Post author

      So true! I’ll admit I never had a pair in my closet until last year when I picked up the leopard print ones I have pictured. My fall wardrobe can be so drab sometimes, so it’s great to have a pair of fun shoes on hand to spice up my outfits – plus they totally make a statement!

      Reply
  5. sidesmile style

    great boot guide! you definitely covered all of your bases 🙂 I love those leopard ones, they are next on my list!! Thanks for all of your sweet comments lately! Hopefully now that things have calmed down a bit I can get back to commenting more regularly 🙂

    xo SideSmile,
    Ashley

    SideSmile Style Blog

    Reply
    1. twenty-something Post author

      Thanks Ashley, can’t wait to see what your leopard booties look like! And you are so welcome – I love reading your blog and you have amazing style. Thanks for taking the time to comment back 🙂

      Reply
  6. thestatestreetedit

    Oops! The comment you just got from tuesdayswithmorrison was me – logged into the wrong blog! 🙂 I’ll repost with the right one haha:

    Oh, I’ve been looking forward to this post! This is absolutely, positively fantastic. I am head over heels in love with the leopard print booties but I would happily raid your closet for any of these options I hope we see more of your shoe collection in the future!

    Reply
    1. twenty-something Post author

      Haha that’s ok!! And thank you – I hope to feature my shoes more often, but sometimes it’s just not practical for me to wear my fancy heels to the office. I can’t wait for fall to roll around so I can wear all the boots in this post!

      Reply
  7. albucco10

    OK–I’m really hoping and praying we have the same foot size. We can do sisterhood of the traveling boot from Florida to NYC! All of these are so adorable, and really similar to what I’ve collected throughout the years. I found myself buying kind of cheapo “leather” boots each season and figured with all the money I was spending, I should just splurge on a good pair that I’ll have for a while. I got a pair of riding ones from Madewell that I’m obsessed with (and they’re amazing quality). I can’t wait to break them out this season!
    -Alyssa
    The Glossy Life

    Reply
    1. twenty-something Post author

      Size 7? I’m game for a cross country shoe swap! I did the same thing for so long, I’d invest in a pair that cost me maybe $30, they wonder why they were completely destroyed after only a season. Last year I spent a lot more on a few pairs in genuine leather and suede and they are all in perfect condition for this year!

      Reply
  8. Rachel @ Making Life Fabulous

    Such good and timely advice! Last year, I bought a pair of dark grey high heeled ankle boots, and wore them all the time! This year, I really want to find the perfect pair of flat riding-style boots. I think I’ll splurge on real leather in hopes they will last for a while.

    Reply
    1. twenty-something Post author

      I definitely recommend splurging a little – my riding boots pictured here were bought last year and they held up amazingly well and are still in great condition for this year. It seems easier to buy a new cheap pair each season, but splurging for genuine leather or suede will definitely save you money in the long run!

      Reply
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