Pants at Boots

Reader Susan emailed me to ask how to choose the right boots to go with your dresses, and I had to admit to her that I am (as the Brits say) pants at choosing boots. I have boots, certainly, but I don't have any boots that I consider successful, where "successful" means that I wear them constantly (and am always looking for more excuses to wear them).

In fact, I think the last pair of boots I bought that I felt that way about were some that I saw in a spread in Jane magazine back in the grungey 90s. They looked great with vintage dresses, especially if you were nineteen.

(Of course, in my opinion, that was the last time a fashion magazine was helpful about boots: what is up with the current craze for deranged-elf ankle boots worn with jersey mini-dresses and all the jewelry you own, plus a knit scarf? Yes, Lucky, I'm looking at you.)

Anyway, not only am I pants at boots, I have realized that I'm pitiably one-track with other shoes, as well — check out what I found when I tidied up my closet:

Erin's shoes

Yep, that's roughly a dozen pairs of round-toe ankle-strap heels. And I'm not even showing you the picture that's all flat black penny loafers!

It might just be that there aren't any boots that look "right" with 1950s styles, other than those plastic rain boots they used to advertise in the back of Parade, the kind that come with a matching bonnet to protect your hairstyle. So I throw the question open to you. What are the best boots to wear with vintage dresses?

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48 thoughts on “Pants at Boots

  1. Hmmm, Erin, you have me thinking. I am a boots person – I live for the day that the weather turns here in Toronto and I get to pull out the tights and boots. The thing is, I am a forties person and most of my vintage is pre-1950. Because of the narrower and shorter skirts I can get away with my mid-calf length brown buckled boots AND my flat riding boots (every pair of boots I covet seems to channel Molly Ringwald in the Breakfast Club) and my Louis-heeled Fluevogs from about 13 years ago. I am not sure what would work with those full fifties skirts. Maybe a pointier toe and kitten heel?

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  2. I covet your shoes! Especially that adorable turquoise pair! Lovely!I hate the deranged elf booties as well. Nothing makes me look stumpier. Blech. Makes me think of the 80’s, with stirrup pants ending in a pair of those boots. Ick.

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  3. I’m not 19 anymore, but I wear my Double-H Jump boots (discontinued, but still available in limited sizes from Shoeline.com) with everything except my skinny cigarette pants.As Emily points out, though, that style of boot really doesn’t work with skirts fuller than A-line. Luckily, windy Kansas winters mean my winter skirts are all pretty slim. And wool. Why doesn’t Blogger allow the TARGET=”_blank” attribute in a link? That’s just dumb. I hate getting directed away from the page I was reading. Gah.–Lydia

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  4. I love flat black penny loafers! I think they’re just as versatile and much more interesting than black ballet flats. I love boots but I can never find the right kind, but I think that the ideal shoes for vintage dresses would be flat riding boots in supple, but somewhat worm dark brown leather, with a rounder toe, or there are three shoe trends that look great in black with black tights: 60s court shoes, high-heeled oxfords, or flat jazz shoes.

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  5. I love wearing dresses and boots, too and have about 9 pair. When I think of full skirts (50’s or otherwise) I think cowboy boots. In fact I’ll wear cowboy boots with almost anything. Last night I wore a very fitted, above the knee sheath I’d made with dark brown barc cloth (banana leaves and all) with a pair of two-toned brown cowboy boots and very sparkly green earrings to a quite fancy restaurant. I felt great. I’ve worn the same dress with knee-hi suede zip-ups with 4″ heels, too, but cowboy boots step everything up a notch. Some people may not understand the cool-level with which you stride but they’ll definitively sense that you know something they don’t know. Like how to have fun!

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  6. What about Frye boots?or these boots: these: these:, I echo Libby’s comment about cowboy boots. Those would have been my first suggestion if she hadn’t already beat me to it.I’m not good with boots, myself. And certainly not HEELS. But for those who are, I guess there are more options. Personally, I just put on the legwarmers for between the moments when I’m outdoors, then peel them off when I get inside.

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  7. I am totally in love with these, and wear them with everything: are the ones I’m coveting, and would wear with anything: don’t work for timberland, I swear!)

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  8. Who cares if you have a dozen pairs of round-toed ankle-straps when they’re all soo adorable?I giggled at “pants.” One of my London housemates was a big burly guy from Shropshire who used call everything “pants.” He was my Eastenders watching buddy. I think Luke would agree that the elfin boot look is absolutely pants.

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  9. I 2nd the vote for Frye boots. I have a pair that I wear with all my winter vintage including a Kennedy era, fuscia boucle suit. I’m sure the previous owner is turning over in her grave but I love it.

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  10. I love round-toe ankle-strap shoes! Can one have _too many_ pairs? NO! I have a pair of vintage Zodiac boots, slightly Western style, but versatile enough to wear with any style of skirt or dress. Also a pair of black leather knee-high boots with a slightly rounded toe and 2.5″ heel that works with most skirts and dresses. One pair of flat-heeled boots in brown suede and one in black leather that both go well with ankle-length skirts. I rarely wear dress slacks and opt for heels when I do. Nothing is more goofy-looking than short boots exposed by pant legs riding up when you sit down..ick! 🙂

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  11. I think most 50s styles simply looks best with shoes, not boots. (The exception being a late-50s boxy suit, which can carry heeled boots just fine.) But when boots are necessary, slip on a pair of fur-trimmed vintage rubber galoshes, right over the shoes. You need the kind with a space for a heel. Took me about 10 tries, but I finally landed a pair on Ebay, and they are sooo convenient and chic.

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  12. Those elfin booties always remind me of the rain galoshes that Ginger Rogers used to pull on over her heels. I love those old fashioned galoshes. If you had a pair of those you could wear your beautiful green suede shoes even if it was raining!

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  13. Although I love to look at your vintage dresses, I don’t wear them myself. However, I do wear skirts a lot and have a ton of boots! The first thing is to get a pair of boots that fits your calves. Otherwise they just look sloppy. For longer skirts, I will wear the shorter heeled boots, but for the ones that land just below the knee I wear a higher heel, sleeker boot. My favorite boots for fit and longevity are Nine West. I work in an office so some of the boots mentioned above wouldn’t work for me…I need the dressier variety.

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  14. i absolutely agree with libby on the cowboy boots, but if you want something less conspicuous, i would suggest upper-mid-calf boots that are tight around your leg. If you wear them with tights in the same colour, your legs will look longer (and you’ll avoid the pixie-boots-my-leg-consists-of-six-short-pieces-look).

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  15. I agree with the other comments about the low heeled calf high boots to wear with the 50’s style skirts and dresses. The heavy and clunky boots with those very lady like clothes look more like funky, thrift store college girl then classy woman. Just depends on what look you are gong for.

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  16. Erin, thank you so much for sharing a snippet of your closet! I had not expected such high heels for you, I picture you dashing about, moving too quickly for heels. They are all so gorgeous, I love that style! I am madly in love with two pairs of my boots, after saving my money for them and searching, I went a full year between buying and wearing them. I was too afraid to scuff them so I’d only wear them around the house, then I’d carefully put them back in their boxes with all the wrapping. I think the right pair of knee-high boots can go with anything, just buy the pair that speaks to your personality and heart (and that doesn’t hurt your toes). A good pair of leather boots should last many many years if cared for, so they’re worth the investment. My favorite have 2.5″ delicate heels, smooth round toes, and a thin bow at the ankle seam. I wear A-line skirts, but full would work fine also. Calf or ankle length boots you have to really look at where the lines are hitting, since the top of the boot will draw attention to that part of the leg, and you don’t want an awkward gap between the bottom of the hem and the top of the boot.I need to finish my fall dresses (one’s a duro) to go with my boots, I’m running out of fall!

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  17. I bought a pair of custom-calf boots from duoboots.com, just a plain black leather with a thicker heel (the Zamora), and it works well with all my 50’s style housedresses. I have some dressier stuff that I’ve been eyeballing a plain suede boot for, mostly because the vintage I tend to own is splashy. Nice prints, great details, I don’t want the focus taken from the vintage! Until that time, I usually pair up my vintage ohmygodlookatthatdress with a pair of great rounded toe t-straps. Like these 🙂 the ones below would work in a pinch, and are much nicer on the wallet)

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  18. If you need a serious, weatherproof winter boot, La Canadienne is featuring some new styles — with a rounded toe and kitten-type heel — that evoke those round-toe, ankle-strap pumps. I think these would look great with vintage fashions.

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  19. I’m of the school that it’s not period correct to wear boots with 50s dresses. Of course if you’re young and slim you can get away with clunky boots with a full skirt! In those days ladies removed their boots once they came indoors. My mother had a great pair of low heeled ankle height boots, which zipped up the front and were trimmed with fur. I loved to put them on and clunk around the house…it was the fur-trim which was so appealing. So cute!My daughter now wears my favourite boots from the 70s, and gets lots of compliments on them. They are pull-on, slouchy at the ankle and high heeled in a gorgeous Italian leather. They look great with straight or full skirts. I took immaculate care of them, with a yearly trip to shoe repair.I purchased a pair of Balenciaga boots made for a dept. store in Europe, which I have yet to wear out of the house. They are just above ankle height with a tubular quilted top, zipper down the back,high heels and a pointed box toe. They are exquisite, but I just don’t know how long I will last on the heels anymore. Needless to say my daughters are chomping at the bit! They’re always snooping around in my closet.Erin, I adore all your shoes, being a big fan of ankle straps myself. Whenever they are in style I buy them. The other type of shoe I love is a Tango type shoe or a 20s shoe with a Louis heel. Have a look at these: Prices for dance shoes are pretty good, considering the high level of quality and the fact that they are well-padded.

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  20. I know some people have mentioned riding boots, and it’s the way to go. Most of my vintage dresses are more summery, so I put them away for the winter, but I wear my low heeled knee high, almond toe riding boots with my 60’s wool skirts all winter.

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  21. As someone who grew up in the 1950s -yes I’m that old, I was born in 1949 – I remember no boots at all from that time except old women’s’ sheepskin ones with a zipper up the front, and regular wellie boots. They really came back into fashion in the early 1960s with Mary Quant and the mod look, -which I loved, as a young teenager then.Maybe that’s why you can’t find anything compatible.

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  22. I think as long as you choose a boot that is similar to the rain boot in that it hits the widest part of you calf, OR, if someone absolutely adores shoe-boots/booties/shoeties/whatever, the split in the bootie must be low enough that the ankle is visible, like a pump. I made a little test on Polyvore:

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  23. I just bought some La Canadienne boots this fall and let me tell you — they are great! They’re comfortable and warm and I could walk and walk in them. They were a great investment and now I have a pair of winter boots that aren’t Sorels!

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  24. Yes, I have to second (or was it third?) the la Canadienne recommendation. I have a pair that I love and whenever I wear them people say I’m looking great. They’re curvy but the heel isn’t too high. And they’re lined with thinsulate or something, so they’re quite warm, and supposedly they’re water resistant. Spendy, but well-made (they were a gift).Also, they have some cute curvy tall boots at Infinity shoes – they have some of those horrible slouchy elfin things, too, but they have some nice curvy Victorian-inspired boots that bring out my secret inner goth girl. Did I mention they’re ON SALE? I really really want the Apex style. Still out of my budget tho; and I already have some knee-high lace-ups. They have some great ones in red and green too – lovely dark red and olive-leaf green. *want*I think calf- or knee-high is the way to go with full skirts, generally. And the fellas *love* them – too bad I don’t love fellas that much ;^) (No offense to them.) But those high boots are like catnip.Oh, and my friend got some great knee-high boots from Fleuvog – also broke the bank but they are HOT! And have a sexy but sturdy, not-too-high heel, important for those of us ladies who walk a lot.I like cowboy boots too, but I never feel lanky enough for them. And the tall riding boots or tall biker boots could work, too. Man, am I jonesing for shoes right now!

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  25. Oh, Erin, no! How could you? Of COURSE we can wear boots with 50s styles! I wear virtually nothing BUT boots! I actually ran into an old boss of mine, and he recognized me feet first, saying, Id know those boots anywhere! The boot I wear most often is a low-heeled, hand-stitched hybrid, a little less clunky than an engineer boot or a motorcycle boot, but much more substantial than a riding boot, and comfortable winter and summer.My personal preference is that the hem hit/cover the top of the boot; if it doesn’t, I try to make sure that there are tights in a colour to match the boot. I actually love the little elf boots; proportionally, they work well with both very short and very long skirts. I also have some over-the-knee elf-boots; very medieval, which I like. I wear a very low heel: kitten, Louis, or riding-boot style. I think any of these work with full or straight skirts, but I think that the Louis heel, often found on lace-up Victorian-style boots, looks very graceful with the full-skirted 50s silhouette. (I would love to be able to wear high-heeled shoes and boots, but its not going to happen any more.)And youre not pitiably one-track, you have a highly-defined style. If you like them, why shouldnt you have them in every colour of the rainbow, every heel height youre comfortable with, and decorated however you choose?I do that with my boots: they range from ankle-high to thigh-high, black, gold, silver, pink, lime green, burgundy, brown, caramel, cream, black-and-white spectator, embroidered black velvet, leopard … and there are many more that Id love to get! I have one pair that are unlikely to go out of the house, though; theyre a delicate oyster suede, with gold toe-caps. Theyre lovely, but Im afraid to wear them outside.I do have some flat shoes as well … there are never enough shoes and boots!

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  26. OMG. I just went to Zappo’s, and La Canadienne’s Tahra and Taylor styles would both be perfect, IMO, for wearing with vintage dresses, both 50s and other eras. They’re apparently comfortable, as well as gorgeous. My only problem is that they average just over $300 per pair. Maybe the Money Fairy will leave a package under my pillow, because I’d say that these boots would eliminate the need for many others – not something I say lightly!Curse you, Anonymous – and thank you!

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  27. Gosh, I love me some boots, although, to be fair, I am in no way period-correct about wearing them with vintage. It gets quite cold and very snowy where I live, and I really like avoiding frostbite when I wait for the bus.But, with that said, I like a bit of contrast with my vintage dresses – some bits and pieces that work because they contrast a bit, not match perfectly. And so, my boots include knee-high riding inspired boots, vintage boiled wool ankle boots lined in shearling, simple flat ones, granny boots, and square- and pointed- toe cowboy boots that pretty much go with whatever I feel like wearing them with that day. Although, my favourite right now that I don’t have a pair of are knee-high lace-up almost-granny-inspired. One day I shall get a pair.

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  28. Once again, I agree with everything la belladonna says (how does she do it?) – knee-length boots and preferably no gap between skirt and boot. On the rare occasions that I force myself to wear a skirt (I’m working on it), I always wear boots because for some reason I find heels with skirts on me a bit funny-looking. I’m currently trying to track down a pair of these in my size (sorry for the Amazon link, Clarks has the most annoying website), as they’re a slightly lower heel than my current pair so might be more comfortable for extensive walking, but they’re pretty similar to my current pair.

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  29. I own a pair of shoes like your robin egg blue ones, only in red. Man, I wish I had those blue ones. Too pretty!I am no help with the boots. I hardly ever wear them.

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  30. Ah! I’m so happy that I finally have something to say in the comments here! I spent two years searching for the perfect boots. I like to wear full knee-length skirts in the winter and I walk alot, so cute retro heels won’t do it for me. I finally picked the winter ridge boots from LL Bean. They’re almost flat, but give me an extra half inch and so lovely and warm! they’re a little slouchier than those La Canadiennes, but they’ve taken me very nicely from Paris (where I live) to Vermont (where I go to school for a week in February), and I expect that if I learned how to use shoe polish they would go even farther. I think the trick to wearing boots with a full skirt is making sure that the skirt doesn’t cover the top of the boot, there needs to be an inch or so of clearance. Otherwise you look stumpy. I’m short, so a lot of off the rack skirts and dresses hit mid-calf on me which is always a problem with mid-calf boots. Find something that fits as cleanly as possible in the upper calf. I find that a little slouchiness in the ankle usually looks ok if the boots are fitted at the top of the calf. Ankle boots are a wardrobe staple for me, but I think they look kinda silly with a fuller skirt (unless they have the furry tops. those are supercute.)So yeah, I second all those people who said a riding boot. After reading all this I’m gonna spend the next two years looking for the perfect t-straps!

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  31. Can there be a hard and fast rule how to wear vintage inspired dresses? There may have been no boots in the 50ies, but there were hats!So those who want to go the whole hog, hat, batwing eyeglasses, murder weapon like handbags, gloves – will leave the boots at home and freeze.The others do what this wonderful blog is all about: wear what makes them happy. Thank you Erin!

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  32. I’m an 80’s girl. I wear my cowboy boots with EVERYTHING. Mine are the black cherry Luccese’s. And they work with black red brown and every other color. Also with any length skirt. (Alas can’t wear them in winter in Norway as I would kill myself on the ice and snow.) But, as an 80’s girl, I also love a cute vintage dress with roughty-toughty biker or combat boots, or really any lace up boot. That’s my punk side showing. Plus I CAN wear that in winter.

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  33. As the previous poster said, no, women weren’t wearing boots with their frocks in the ’50s, but neither should we take to wearing bullet-proof breast jails, vulcanized rubber girdles, or gloves all the time. Well, okay, yes on the gloves. I wear a pair of black boots with a flat heel. They are a tad bit “motorcycle-y”, but not too much. I also have a pair of very tall brown boots with a wooden stacked heel-4 1/2 inches!! Both go well with my dresses. I have a hard time with finding boots because I have large feet, thin calves, and long shins. I usually swim in the boots or they are way too short for me. I have always lusted after cowboy boots, but they look like skis on me-totally crazy.

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  34. Round-toe ankle strap shoes are the BEST!!!!! Unfortunately, I don’t think I even own one pair at the moment. (It sucks having size 10.5 feet!!) But you’ve inspired me to start hunting some down! 😀

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  35. I wear two types of boots i think look right with full-skirted 50s dresses…i think both end up appropriate to the silhouette–one pair are round toe kitten heels (the pointyness of the heel keeps it 50s-ish)–would be ok with pointy-toe kitten heel too. the other i’m still looking for a good pair of, and those are pointy-toed stiletto heel boots, the boot equivalent of the 50s stiletto. i’m no good with high heels so finding ones one can walk long distances in is near-impossible. i think both update the 50s silhouette nicely, too.

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  36. 1. I love your shoes!2. Boots go with most things, but the key is to accessorize and layer properly so they don’t look like you just stuck big heavy boots with something they don’t belong with.3. I hate ankle boots too. They make everyone’s legs look stubby. Why don’t fashion magazines realize this?4. Who said something mean to you? What an asshole… Try boots, once you start you can’t stop!

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  37. I’m still a n00b with boots as well, but I do know that I want those super cute baby blue round toe strappy ankle shoes at the top left of your picture! CUTE!

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  38. I love the light blue pair of heels in the pic!! anyway to find out where you got them or at least the name brand? I’m getting married in september and is the pair I’ve been looking for!!

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  39. crazy question, what size are they? can i buy or borrow them? I’ve been searching the net for months trying to find the perfect pair of blue shoes for my 50’s themed wedding. And when I finally find them, I can’t find them for sale anywhere. I’ve searched every webpage and even tried contacting the designer, I know its crazy but I figured its worth a shot! Thanks

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