Fashion Friday: Boots

Here’s where I want to start with boots.

There’s this tricky fashion conundrum I’ve been wrestling with for some time. I keep trying to find shoes that look dressy and non-frumpy with skirts and dresses, and that are comfortable enough to walk in for miles.

I walk a lot. Walking is my main form of transportation. If the place I’m going to is an hour’s walk or less, I will almost always walk. It’s exercise; it gets me outside into the sunshine and the world; and I know exactly how long it’s going to take me to get where I’m going, without having to build in a cushion for late buses or bad traffic. Besides, I just love it. Walking a lot feels physically good.

But walking a lot means that my everyday shoes need to be super-comfortable. And I don’t mean “comfortable enough to walk in for a few blocks,” or, “comfortable enough to wear to work when I’m sitting most of the time and walking to other people’s desks now and then,” or, “comfortable enough to stand around at a cocktail party for an hour.” I mean, “comfortable enough to walk in for miles.”

So I need shoes that I can walk for miles in. And at least sometimes, I want to look dressy and non-frumpy when I get there.

(Tangent: And do not freaking tell me about ballerina flats. I don’t know if I have weird feet, or have been buying the wrong ballerina flats, or what. But every pair of ballerina flats I have ever owned has provided me with zero arch support, and has chewed the hell out of the backs of my ankles to boot. My four-inch stilettos are more comfortable. I keep trying, and I keep thinking that this time will be different, and I keep being disappointed yet again.)

My answer, so far: Boots.

Boots look freaking awesome with skirts and dresses. They can look sporty. Rakish. Tough. Sexy. Cutting-edge, retro, timeless. Delicately feminine, swaggeringly masculine, entertainingly genderfucked.

And — very importantly — they do not have to have high heels to look freaking awesome. Low or flat- heeled boots — ankle boots, knee boots, thigh boots — can look entirely gorgeous.

So I can walk in them for miles. I have boots that are more comfortable to walk in than sneakers.

And voila! Dressy and non-frumpy with skirts and dresses; comfortable enough to walk in for miles. Conundrum solved. (Much of the time, anyway.)

But there’s more to it than that. Like I wrote a few weeks ago, in my disquisition on shoes and why so many women get so obsessed with them: Shoes affect how you stand and walk. And in boots, the way I stand and walk is confident, assertive, even athletic. In boots, I have a strong stance, an easy stride. Boots — flat- or low- heeled boots, anyway — give an air of freedom, of being ready for anything: ready to walk for miles, climb a fence, run for a bus, run from the cops, kick someone in the balls, dance all night, fuck all night. Just by how you stand and walk in them.

I guess what I’m saying is: Power.

There’s something about that blend of comfort and confidence, ease and roughness, earthy practicality and showy swagger. It all adds up to power. They make me feel like a pirate. A superhero. Amelia Earhart. Emma Peel.

And, of course, there’s the fetishy aspect. Boots, for whatever obscure reasons buried in the history of sexual culture, are considered by many to be kinky and domme-y and fetishy. Less so with low- and flat-heeled boots — but even those tap into the archetype to at least some extent. (And depending on the low-heeled boots, they can tap into a stone butch or Tom of Finland archetype, if that’s what you’re going for.) Boots, for many people, evoke John Willie and Dita von Teese, Sacher-Masoch and the Velvet Underground’s whiplash girl-child in the dark. And even for people who don’t go there consciously, the echoes and shadows and implications are often still there.

And that makes them powerful, too.

Boots aren’t always perfect. They’re sporty and rakish and so on… which means that for some events and outfits, they’re just not dressy enough, or elegant enough. Sometimes you really need something delicate and strappy and subtle, or delicate and strappy and not-so-subtle. (A different kind of power.) I’m still on the hunt for the perfect pair of dressy, non-frumpy, shoes that I can walk in for miles. Of the non-boot variety, that is.

But the boot variety makes me pretty freaking happy.

Fashion Friday: Boots

34 thoughts on “Fashion Friday: Boots

  1. Tom

    You can wear what you feel looks nice, but I spend very little on the vanity portion. Luckily my fashion sense corresponds to less expensive and I couldn’t tell you a single designer name, unless “Target” counts.

  2. 3

    I lust after any boots I see that look like what you describe. I keep wondering if my trip to Cancun in 2 weeks is really worth not buying the boots I need. (Need, not want, for all the reasons you mention, plus weather).

    I have one pair right now, that were men’s, but Italian, so pretty femmy…okay they look like army boots, but not like men’s army boots. afaik. I bought them in 2001, and I keep gluing the soles back on. I worry this can’t last forever. I still have 5? pairs of heeled boots, but I max out at about a mile in those. I can make it to the party, but never home from, walking.

    Anyone have any brand recommendations? Fluevog maybe? Must be flat, as my city is hilly. Also, I fall over in platforms (even while sober). And, can I justify spending over $100 or $150?

  3. 4

    Boots are the best. If you in an area with a real fall and winter, boots are very practical, too. I walk a lot, too, and nice, leather boots are a great alternative to tennis shoes and uggs and whatever ugly footwear people wear in cold climes. I wish I could wear boots all year round, but in summer it’s not practical. I’m just sad that boots are more expensive than most sandals and flats.

  4. 5

    You’re not the only woman with complaints about ballet flats. I just love the idea of ballet flats, but the damn things just won’t stay on my feet. The back end keeps falling off my heel, so no go.

    I don’t actually own any boots except for the enormous clunky pair I bought a size and a half too large because my size wasn’t available at the time. They are, needless to say, problematic to wear. I’m hesitant to buy more boots because I’m one of those weird women who think shoes should be as inconspicuous as possible, so I’m not comfortable with the money or space it would take to have nicer boots. BUT! I do love the way boots look on other women.

  5. 6

    That’s why I love my riding boots. I have a pair of knee-high boots that I mainly bought for horseback riding, but now that boots and tight pants are “in” I wear my boots and breeches everywhere. 😀 Weather permitting. of course. I live in MN, and they’re not the warmest, so they’re on vacation temporarily. 🙁

    Here’s a good tip for breaking in tight leather boots: put them on and get them wet with warm water. I mean so soaking wet that you can feel them squish as you walk. And here’s the really important part, wear them until they completely dry. And just to be safe, for an hour afterwards. They’ll feel like they’re custom-made and it won’t ruin the leather if you condition them afterward. Worked so well for my boots and now they’re unbelievably comfortable.

  6. 8

    Fluevogs are good, but very pricey. Doc Martin’s has a lot of variety in their womens’ boots now, and those (used to, not sure about now) last forever, and aren’t prohibitively expensive. If they’re still made in England by the same factory, they should be okay. I haven’t had a new pair in almost 20 years, and that pair finally died an honorable death a few years ago.

    Regarding boots generally, they are my weakness when shoe shopping. I don’t need any more. I have tall black ones, short black ones, short brown ones, mid-calf brown ones, etc., but they still call out to me. I feel like I need more. I feel sassy and sexy in boots. I even have a pair of custom Lucchese cowboy boots that I won in a contest a few years ago. If my place ever caught fire, I think I would grab those.

  7. 9

    Which language was that in? I can read Tok Pisin (an English Pidgin) better than that despite never having learned it (just going on the similarities with English and what little I know about the grammar).

    Fashion definitely is a language. Not in the way you state incorrectly all so often but in the way that it has many different terms and constructions which seem to mean nothing to the uninitiated.

  8. 10

    I once heard a discussion about thigh length boots on BBC Radio 4. The all female panel seemed to be in agreement that only a certain number of women can look good in them. One described seeing a woman dressed in thigh boots and very revealing hot pants. Her thighs were a bit too plump and because of the way that the boots squeezed them into a rounded shape at the top, she looked as though she had four buttocks. I thought this was hilariously funny and reflected on the fact that sometimes radio produces the best images.

  9. 11

    And this post illustrates why I love reading your stuff so much. I, too, love boots (and shoes in general) and also want all my shoes to be comfy. I gave up the ballerina flats after working in a building with marbles floors after college. You need shoes with soles in that place!

    So I come to your posts knowing I’ll get something good to read, something that expands my mind in new directions and something that will make me smile and say ‘Awwww!’. Such as the kitty pics.

    Thanks to you for being so much fun in all areas. It’s a gift to be able to write so well about…everything. And your appreciated.

    Happy Saturnalia!

  10. 13

    I totes lurve high boots but my calves are usually too large to fit in them and I can’t afford custom made at this point in my life. I did, however, spend many, many years happily trotting along in my Doc Martens and I would wear them with ANYTHING.

  11. 14

    Check out thrift stores near military bases. The enlisted are encouraged to get new boots regularly, so near-pristine boots are plentiful. They shine up well, keep out water, are manufactured for a wide variety of foot types, and you KNOW they’re made for walking. There are prettier boots out there, true, but few of those are as well-made, and fewer still as cheap.

    There are many versions made, but my current all-leather companions manage a certain elegance, lace up (and are thrown off) quickly, and have a heel that plays well with my bicycle’s pedals. ($7 from Goodwill)

    Thanks for the ode to boots, Greta Christina! It needs saying.

  12. 15

    Have you checked into Cydwoq shoes? They look amazing and are the most comfortable I’ve ever had for walking (5 miles per day on average).

    My wife turned me on to them several years ago and that’s pretty much all I wear now.

  13. 16

    My motorcycle boots are my favorite shoes and the best 80 bucks I’ve ever spent on shoes. They make me feel very dapper-butch, badass, fuck you society and all that jazz. I love how they look, how they feel and how I stand and walk in them.

  14. 17

    I feel your need to walk to the party in something comfortable. Depending on the event, I will change shoes when I get there. Or wear pants, which hide the upper and leave me with something that looks dressier on the foot than it actually is.

    Also, the idea that ballet flats are actually worthwhile for walking is some kind of pervasive myth. How can something with no arch support and very little sole be comfy?

  15. 18

    If you’re looking for a dressy, comfortable *shoe* that’s non-frumpy, you might want to check out what are called “character shoes”. They’re made for wearing by stage actresses (well, while guys could wear them, I have yet to meet one who has…and they’re not my thing), and are usually available in dance / stage apparel stores.

    Here’s a link to one I found while searching (since I couldn’t remember “character shoe”):

    All credit goes to the director and stage crew of a performance I was in; the director swears by hers, and the stage manager and assistant said they’re big fans of theirs, too.

  16. 19

    I just bought a pair of tall black Born boots and I loooooove them. Super comfortable and they work for my business-casual work environment. They weren’t cheap – on sale at $170 – but worth every penny in comfort and every day wear-ability.

  17. 20

    I love boots — I have two pairs, one with chunky heels and one flat — but apparently the fashion industry has decided that my calves are too freakishly big, so boot-shopping is difficult. The only way to find boots that fit past my ankles is to go for the Wide variety, and those are generally an inch or two too wide and end up hanging like floopy pirate boots. This is not necessarily a bad look, but it’s not a look I want to sport 100% of the time. I also want to find calf-high boots I can bike in (a friend has a pair and, with brightly-colored over-the-knee socks, they are incredibly fun and hot), but I can’t find any for less than $150.

    So boots are very problematic for me (as are pants).

  18. 21

    I love boots.

    However, I’m low income. I can’t afford a decent pair of boots. I recently saved up and with help managed to afford $200 to fix a long-standing cavity in one of my teeth. Tell me how I am supposed to afford a pair of boots which cost $150 at the very least?

    Then there’s the calf thing. The fact that I’m the third person to mention this is telling me that it’s actually a pretty widespread problem. Lots of women don’t have skinny calves, but the fashion industry doesn’t care because it’s the fucking fashion industry.

    So, I have a $40 pair of ankle-high flat boots which are only a month old and are already showing signs of breaking apart, and a $70 of calf-high boots with heels that are actually pretty decent. But I really, really want a pair of boots that resemble the picture Christina used to illustrate this post. Maybe someday when I’m working a real job instead of being a dishwasher.

  19. 22

    “Nanny {Ogg} raised the hem of her skirt. She was wearing new boots. As boots, Granny Weatherwax could find nothing to complain of in them. They were of proper witch construction, which is to say that a loaded cart could have run over them without causing a dent in the dense leather. As boots, the only thing wrong with them was the color.

    ‘Red?’ said Granny. ‘That’s no color for a witch’s boots!’

    “‘I likes ’em,’ said Nanny.

    “Granny sniffed. ‘You can please yourself, I’m sure,’ she said. ‘I’m sure in foreign parts they goes in for all sorts of outlandish things. But you know what they say about women who wear red boots.’

    “‘Just so long as they also say they’ve got dry feet,’ said Nanny cheerfully.”

  20. 23

    I totally, TOTALLY feel you on ballet flats. I think they’re evil. Cute sometimes, but evil nevertheless. At a recent convention, I wore 4in platform stillettos on one day, and ballet flats the other. My feet ached so much more on the day I wore ballet flats.

    And like you, I love boots too! I especially love knee-high kickass boots, but unfortunately it’s too hot for them most of the time where I am.

    I have found my perfect cute-but-still-can-walk-for-miles shoes though: platform wedges. I love those things to bits. However, many people I know find them uncomfortable, even if to me they’re the best things ever, so YMMV.

  21. 25

    I’m completely mad for boots. Obsessed, even. From the thigh high fuck me boots I have for the bedroom to the stylish walking around boots I wear to work. Fetish? Yeah, sure. But fashion, too. I love em.

    (Oh, and both times I’ve seen you speak, you’ve had killer boots; please pardon my insane envy).

  22. 26

    I looovvve the look of boots, but I’ve got amazingly hot feet. I live in lowland Northern California, where it doesn’t freeze, and for everyday I wear breathable cloth mules all year round. (I’d wear sandals, but I haven’t found a brand compatible with my orthotics.) Even in the rain, I find the cloth shoes dry quickly and my feet never get cold.

    When I go hiking I wear an amazingly comfortable pair of hiking boots, but even in cold weather, when I take them off, I can wring out the socks.


  23. 27

    I love boots! I just got two new pairs for winter. One pair is slightly metallic and badass with straps, the other pair is knee-high and sort of dressy. They were overdue – I think the last non-snow-boots that actually belonged to me were purchased from Hot Topic in sophomore year of high school, and I’ve been done with college for two years now. I’d probably still wear them, except I can’t walk in heels at all anymore. I shouldn’t wear ballet flats – my feet hate me and need better support than that, but I did for a long time… with little bows, of course… At least now I think I’m getting past my “cutesy” phase. And for sure I’m past my “pain for beauty” phase.

  24. 28

    I, too, love The Boots, and can wear them all winter in a snowy climate and then in the summer in the desert.
    Frye engineer boots have a lethally slick sole on their own for icy/snowy conditions or wet tile floors (as do all Frye boots, apparently), but you can get rubber soles glued on, and I just saw that now they seem to be making that -one- boot at least with a rubber sole. Their women’s flat thigh-high-converts-to-knee-high boot looks fantastic.
    Spent time working outside in the desert in my short skort, a black tank top, and my Frye boots and it is STILL the best date outfit I’ve ever had, even covered in dust and sand!

    Aerosole, by the way, makes surprisingly durable boots, and the soles are good on wet or ice – and they make narrows, have arch support, and come with wide calf models for some styles.

  25. 29

    I love boots. I do wish I could afford them, as they are often very expensive, especially for the very good ones I like. I often just wear a pair of parade boots I got used but I would love to get a pair of RCMP riding boots. Riding boots in general are wonderful though. If I had more money I would get my girlfriend a pair of ballet boots, as we both love the look of them. Obviously those are not going to be walked in very often.

  26. ik

    Kind of wonder why men don’t wear boots with formal-spectrum clothing very much today. It’s one of the biggest of the not very many changes over the century. (along with the disappearance of hats.)

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