Reader Request: How to Shop for Boots


Reader Krysta e-mailed me this question:

I would love to hear some input on the process of finding a good pair of boots! Growing up, boots were always worn with a specific functional purpose in mind, either for dirty messy work or getting in/out of the ski lodge while on vacation. In the past couple of years, as I’ve grown into putting effort into my style, I’ve also started looking for a nice pair of boots. However, everywhere I turn, it feels like I can’t find anything that hits the perfect trifecta of fitting my style, fitting my pinched-penny budget, and fitting me. Looking online at sites like 6pm gets me closer, but I have no idea how to even guess if the boot will fit in the height and calf (valid concerns when you fall well outside the norm in leg-length!). I’d love to be able to pull out a pair of trusty boots as the weather turns cold and wet, but I just can’t seem to make the jump!

I sent Krysta links to my numerous posts about selecting and buying boots, but also realized it might be valuable to compile that information here. Especially since many styles of boots are on MAJOR sale right now (in the northern hemi anyway) and it’s a great time to nab a bargain. For specifics of boot shopping, buying, and wearing, scroll to the end for a list of related posts. But for an overview of boot shopping and selection, read on!

Pre-shopping quiz

Before you head out to ANY stores, sit down and have a think. There are hundreds upon hundreds of boot styles out there, and if you dive in without a plan, you will become overwhelmed and cranky and possibly buy a pair that you’ll regret. So, pour yourself a cuppa and take this pre-boot-shopping quiz:

What are my measurements?
Grab a tape measure and get cozy with your calves. How long are they from arch to mid-knee? How big around are they at their widest point? And although this doesn’t fall under “measurement,” consider where you’d like your boots to hit. For tall boots, an inch or so below the kneecap is ideal. Mid-calf and ankle styles have far more leeway.

Which neutral will I wear most?
Very few women would describe fire engine red or emerald green boots as their ideal. Neutral shades are the most versatile, which makes them your best bet for wise investment. So ask yourself which neutral will get the most wear. For most women, it’s black. But cognac brown goes with EVERYTHING and generally looks more expensive. Also gray is fabulously flexible, and is becoming easier to find in all styles of boot.

Is a heel practical?
If you are on your feet all day then super-tall heels are right out, but can you deal with 1″ or 2″? Are you better off with a flat/riding boot style? Or will these be boots that never walk more than five blocks at a time? Be honest about heel height. Boots with a heel that hurts will not get worn.

Are my feet fussy?
High or fallen arches? Bunions or corns? Need loads of support or flexible soles? Read customer reviews online, check construction, ask questions, do everything you can to make sure that your potential new boots will caress and love your fussy feet. (Check Barking Dog Shoes’ boot recommendations for some ideas.)

Do I have fitting concerns?
If you have wide or narrow calves, small or large feet, or any other traits that make boots tough to fit, you may prefer to shop in person. But if not, I highly recommend going online. I’d try scouring Zappos, Nordstrom, and 6pm for starters to get as much info as you can about brands that will fit your needs. Try Barefoot Tess for larger sizes and DUO for wide and narrow calves. (More resources below.)

What’s my budget?
Multi-purpose boots can be bought cheap, but real leather and quality construction will last longer and be kinder to your feet. Still, never, ever spend more than you can truly afford.

The next and final question on the quiz deserves a little more focus, so let’s tease it out a bit.

What’s my preferred style?

There are hundreds of boot styles available, and with the world of Internet commerce at our fingertips it’s easier than ever to find your dream pair. Do you want riding boots? Heeled tall boots? Short moto boots? Mid-calf slouchy boots?

In my opinion the five most versatile styles of boot are as follows:

  1. Sleek, tall flat boots – riding boots and tall moto boots qualify
  2. Classic tall heeled boots – just below the knee with a 2″ or higher heel
  3. Ankle boots – new to the classics category, but ubiquitous and fun
  4. Tough boots – combat and engineer styles, but also anything with loads of buckles and hardware
  5. Cowgirl boots – even if you aren’t a Western dresser, these can be remarkably useful especially in summer

The first two are the most basic and classic, of course, but if you’re not into tall boots the other three offer great alternatives. Naturally, your perfect boots might not be on this list, but if you’re not sure where to start, these styles have proven themselves over the years as reliably versatile. (Rain/snow boots are essential in many climates, too, but I’m focusing on fashion boots here.)

Once you’ve narrowed down your style choices, start refining by making some decisions about shape. I am most likely to wear classic tall heeled boots and to me, the shape of the boots shown above represent the tall-boot baseline. Those beauties are Frye Marissa Back Zip boots and they’re fantastically spendy, but you can find similarly-shaped boots just about everywhere: Tall shaft, medium heel, solid color including the heel and sole, absolutely no detailing. Even if those boots look far too dull for your taste, it’s often best to begin with a very plain, sleek, pared-down design and THEN start adding embellishments like buckles, slouching, exposed zippers, etc.

So what are your ideal boot’s essential features? A block heel? Below-the-knee shaft height? Full zip? Suede, leather, or vegan? Build your perfect boot in your mind, then see if you can find something similar in the shops or online.

Searching and shopping

You’ve thought, compared, researched, and considered. Now it’s time to shop! If you’re shopping online and can afford to do so, I highly recommend ordering your top three pairs from a free shipping/returns place like Zappos so you can compare them in person, take notes, and send back the duds. If you’re shopping in person, try to visit three or more stores before making a purchase … or have enough budget flexibility to buy more than one pair, compare at home, and make returns. It will likely take some time to find your ideal pair, even if you’ve done your homework. But the payoff will be a pair that lasts for years and suits your style perfectly!

Related posts:

Online boot-buying resources:

  • DUO: Expensive, but beloved for creating hard-to-find narrow and wide calf styles
  • Widewidths: Wide calf options in classic neutrals
  • Zappos and 6pm: These companies have amazing selection and make searching easy. Watch product videos to get a sense of how boots look in action and fit.
  • Nordstrom: Loads of options from budget to designer
  • Barefoot Tess: A great resource for sizes 10 -15

Image courtesy Zappos

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

Originally posted 2014-01-27 06:38:23.

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11 Responses to “Reader Request: How to Shop for Boots”

  1. Kathleen

    Great tips! She mentioned falling well outside the norm in leg-length – I do as well and my greatest boot discovery was that “over-the-knee” boots are perfect “TO-the-knee” boots on me. No more awkward shaft heights!

  2. Natalie

    Excellent suggestions! I love having all this info compiled in one place, Sal.

    When making my first boot purchase, I followed your advice at first (taking my measurements, figuring out which styles I loved and was most likely to wear). Then I went to during a sale and bought the one pair of boots that was the most beautiful of all those boots I found online whose measurements fit my own. They fit like a dream (because of the measurements thing, because they were a high-quality brand, and because my feet aren’t particularly fussy), and I’ve been in love with them ever since. I chose a rich cognac color because I thought that looked best on the leather boot, and adjusted my winter wardrobe to work with my boots.

    I’d add another recommendation: view your first pair of boots as an investment. Get the highest quality you can afford in a style and color you will wear nearly every day, take care of them, and they’ll last for ages. Genuine leather will usually last much longer than man-made materials, so I’d recommend buying leather unless you are ethically opposed.

  3. Shaye

    As someone with wide calves (so wide that even most wide-calf styles are too small for me), I can’t recommend lace-up boots highly enough. A functional lace will enable many boots to adjust to either a wide or narrow calf. Though you might need to get longer laces than the ones they come with!

    I’ve never had a pair of fashion boots that really fit me, until this year, and now I’m wearing my two pairs of lace-ups all the time!

  4. walkercreative

    Thanks for compiling this in one place. Yes, here in the northern hemi (upper Iowa) boots are on sale at steal prices now …. $100 boots going for 30 bucks! I wasn’t sure where to look, and have never invested in “real” boots before. This is a great guide. I did find (during this arctic winter) that I really have no need for shoes from November through February I haven’t worn shoes since October — only ankle, slouch and hiking boots. My fake leather boots have not withstood the cold weather beat-down well. They cracked and leaked. I have wide-calved high-arched fussy cold feet, so my boot investments are going to make or break next winter. TRACTION is another important factor for me . . . you never look cute falling on your rear! Thanks to this guide online shopping is out, (No 6pm or DSW’s here) so off to the stores I go armed with measurements! This is super helpful! Thank you!

    • Natalie

      It sounds like you might want to check out some of the outdoor companies’ women’s boot selections. They make some adorable boots that transition great to wear with nicer clothes that feel amazing on the feet while being waterproof, warm, and non-slippery on ice. I bought a previous year’s model of these on clearance a few years ago, and love them:

      They lace up in the back, so they’re great for adjusting to different calf sizes. They’re cute enough that I wear them with tights and a dress for work as well as for hiking and playing in the snow. They’re my go-to on cold, snowy days. There are a bunch of different styles along these lines available from many outdoor recreation shops. (side note, REI’s return policy is amazing, so you can buy boots online even if you’re concerned the fit won’t be right).

      • walkercreative

        Thanks Natalie — I like the way those look, and they could work with nice clothes too. Maybe I can find them at Active Endeavors or Gander Mountain before ordering online. Great tip, I hadn’t considered the outdoor stores — I am hardly athletic! 🙂

  5. Robin

    A note on zippers: I’ve accepted that I won’t buy a knee-high boot without a full zip. I live in a cool, wet climate and wear layers nearly year-round, which means a lot of sticking leggings- and jeans-clad legs inside tall boots. A half-zip (for those new to boots, that’s mid-calf to foot, with the top of the shaft closed) leaves me wrestling my foot through the top, getting my foot stuck through the open zipper hole, etc. A full zip makes any boots far more likeable in my book.

    Also, from a narrow calf perspective, I totally agree with Shaye about the benefits of lace-ups.

  6. Ellie

    Another calf-related consideration for on-line ordering: height/length of calf muscles, as well as width. I find that wider-calf boots or wide-calf sizes that should fit, in terms of circumference measurements, often don’t because the “wide” part of the shaft doesn’t start low enough—my calf muscles seem to start much closer to my ankles than those of the bootmakers’ lasts! So either I can’t get the zippers to close more than a couple of inches past my ankle bones, or I can wrestle them all the way up only to have the boots slide down and bunch around my ankles.

    Lace-ups might be a good potential solution here, too, because they’d allow for a customized calf height, as well as width.

  7. Paula B

    I just discovered my ankle boots look great with tights and a skirt. I have thick ankles and the ‘just above the ankle’ ankle boots gives me the illusion my calf tapers to a nice slim ankle when in fact it is hidden by the ankle boot. So happy I discovered this as I always thought I had to wear a high boot with dresses or skirts.

  8. Krysta

    Thank you so much Sally!

    I ended up buying two pairs of boots for the season. The first I didn’t pay as much attention to the height as I should have… If I were to wear them the way they’re styled in all of the promo material I saw, they’d be well up my thighs! I lucked out in being able to restyle them, so now they’re almost buccaneer-y, which I love (or they’ll look like cowboy books when under med-wide leg jeans). The second pair looked like they’d be close on the measurements, and again worked out in my favor. I’ve been wearing both a lot the last few months! I pretty much only wear shoes when I can’t get away with the boots.