Ask Allie: All About Shoes

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Oh shoes… one of my favorite subjects!


Flats are a puzzle to me. It seems ballet flats are “the” flat shoe if you want to look fashionable, but I rarely find a pair I think look nice on me. I’m needing a flat shoe that’s versatile, comfy, and looks good. What should I be looking for?

Ballet flats look like crap on me. I have big calves, thick ankles, and fat short feet so ballet flats make it look as though someone lopped off my toes. However, that doesn’t mean I can’t wear any flats. The pointed flat has made a return which makes me AND my non-lopped off tootsies happy. They elongate the leg but still keep your heels close to the ground. I also like the almost-flat (as seen in my leopard flats in this post). A very very low heel or wedge gives a touch of lift which flatters the leg yet is still wearable all day long. Finally, this season has so many flat shoes to choose from that aren’t a typical ballet flat – check out a slipper-inspired flat or a pair of brogues for low-heel comfort but high-octane style!

I’ve always thought you can’t wear ballet flats with socks or pantyhose. For some reason, I feel so dumb when you can see my socks/pantyhose between my shoes and my pants. Are there rules here?

I don’t love the look, but I also don’t love frostbite or hypothermia. Many choose sheer trouser socks for such a situation but I find they don’t offer much more warmth than a bare leg. However, a black textured or patterned sheer hose is a great choice, as is an opaque hose that blends in with the pant and shoe. Steer clear of traditional socks of cotton for they aren’t refined enough, and everyone just accept that we can see your “peds” so either wear a full sock or go sockless, the little beige exposed band just ruins the look of the shoe all together.

I see a lot of open-toed shoes, even now in fall. I’m up in Canada, and obviously, it’s completely ridiculous to think I can go barefoot all winter long! Is it okay to actually wear open-toed shoes in winter with hose of some sort?

Yep, rules have been broken all over the place the past few years. I regularly wear open-toed shoes with opaque hosiery. I either wear the same color hose as the shoe, or else go for a very extreme purposeful contrast.

I purchased black suede high wedge heeled ankle boots from Lands End Canvas that I just love! The wedge heel is a tan rubber material giving it a more casual look, I think. I want to wear them often this fall, but the only way I know how to wear them is with skinny jeans. I see other people wear ankle boots with skirts and dresses and would love some tips on styling the boots. Thank you!

Such a boot would look adorable with black tights, a pleated or fuller short skirt, and most anything on top. Channel 1990s Winona Ryder with such shoes, just put a 2012 spin on it. Floral dresses, denim and leather jackets, even winter shorts with tights would look fantastic with such booties!

Hi Allie, I have a question about wearing black with brown. I have a great pair of brown tall boots and would like to wear them with some black pieces I have but I've heard for so long that it's a fashion no-no to mix the two. Is this a fashion myth or can these two colors be worn together?

I wrote about mixing black and brown here, but for the record I am all for it as long as you do it in a purposeful fashion. Brown boots with black hose and a black dress is quite chic, but brown boots, red tights, black skirt, and blue sweater could make you look as though you dressed in the dark. Using prints to connect the black and brown is an easy way to make the combination look purposeful – I find a leopard print belt, scarf or base layer is a great choice as the print has both black and brown in it!

Hi Allie, I'm a commuter so I like to wear flats or low heeled shoes on my walk to the Metro and then change shoes when I get to work. I typically wear trouser style pants. The problem is that my pants are hemmed to be worn with heels and drag on the ground when I put on flats. Because the pants have wide legs, I can't roll up the cuffs like I would with skinny jeans. Do you have any thoughts on this?

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  1. Should have said purple suede heels Alli & black tea strap suede heels with snap satin white dress & coat ensemble?

    1. I’m not sure what snap satin is. Is it brushed/matte? If so I think this could work. However if it’s traditional satin I’d recommend a lighter weight fabric shoe like crepe, silk, satin, or patent and in a lighter color (blush, nude, metallic). If you do have a dark shoe like purple or black you will want to “bookend it” by bringing darker or heavier colors elsewhere – a black bag, a dark metal cuff bracelet, a darker necklace. Hope this helps!

  2. Allie I hav a pair of black suede heels & pair of black tea strap suede heels , can I wear either pair with a white snap satin dress & coat ensemble on April 1st to a luncheon

  3. “and everyone just accept that we can see your “peds” so either wear a full sock or go sockless, the little beige exposed band just ruins the look of the shoe all together.”
    Finally someone that says it! What’s all this fuss about showing that you are wearing, god forbid, a sock! They are stylish and fashionable clothes afterall, if some days a girl just doesn’t feel like going sockless with flats, even if with a skirt, go ahead and wear a pair of nice ankle socks and give your feet some rest :).

  4. Late response. I always love your posts and style, so I feel strange posting for a first time to disagree with you, but there ya have it.

    A quick thought on ballet flats and socks: For me, it depends on personal style, occasion and the length of the vamp. I won’t typically wear socks with ballet flats with a low vamp, though if anyone can stylistically get away with the bobby socks and ballet flats look (rather 50s or Audrey Hepburn), I say go for it. For ballet flats with a higher vamp, I find I can easily treat them as loafers in the winter, and wear with colorful or patterned or thick or etc. socks. It might depend on how conservative your workplace/personal style is. The only diehard fashion rule for me: Make sure the socks fit your feet and shoes well, so there is no bunching of material on the foot.

    1. I actually am glad you piped up with a disagreement. I think many are scared to, and that’s silly. Your opinion is just as valid as mine and honestly, I am not a ballet flat wearer so hearing from those who wear it… well it’s more authentic. I can only give advice from what I see, so thank you!

  5. I always thought ballet flats looked awful on me, too. I have long feet and short legs and always felt that ballet flats made my feet look like enormous dolphin flippers.

    Anyway, one day I tried on a pair of tan ballet flats with a black cap-toe and for once my feet didn’t look longer than my legs. I also have a pair of red ballet flats with a huge flower on the toe because those also don’t look awful.

    Overall, I prefer pointed toes on all my shoes, but especially low and flat ones. I’m so glad they are coming back in style! Now I just have to figure out how to make platforms go away, too.

  6. Hi Allie. Love your site. You inspire me!

    I have rheumatoid arthritis, which means my feet and ankles are very fragile and I have to wear very supportive shoes – typically lace up ones that take an orthotic device. Sometimes clog shoes are ok. Occasionally, dress shoes that take an orthotic will work, but only for a couple of hours. Most of my shoes are SAS brand. (They really do help my feet. I don’t mean to sound ungrateful.)
    The thing is – the shoes look basically OK with slacks but I love to wear floral print dresses and skirts and don’t want to wear slacks all of the time. But I HAVE to wear shoes that protect my feet. I feel like a dork, and just hope people wont notice or care.
    Any ideas how to make this necessity less dorky?

    1. I guess I stumped even you! That’s OK. Don’t worry about it. It’s a tough question which perhaps has no decent answer. For years I’ve pretended that I don’t care about looking dorky and can just continue doing that.

    2. Okay super delayed, so sorry! I had to wear similar shoes when I was younger due to toe walking and pronation and understand your problem. This season is actually in your favor as lace-up shoes has become quite stylish. Everything from Doc Marten to brogues to lace-up booties and tall boots are on trend, and they don’t require heels to look chic. But I honestly think that your shoes aren’t something you need to focus on, it’s important for your health and comfort and that takes top priority. Matching hosiery to your shoes makes them less obvious, or go the opposite route and make them your signature accessory with fabulous colors and textures. It’s possible to jazz up your shoes, many DIY tips to change finishes, add sparkle, do a faux cap toe etc. on the Internet right now, Google DIY shoe makeover for some fun suggestions. I bet people don’t notice as much as you may think, and if you wear the shoes with confidence others either won’t notice or care. Best to you!! 🙂

      1. Thank you for sharing these good ideas and encouraging thoughts! I’ve been doing the shoe thing since I was a young adult, and it hasn’t hurt me romantically or professionally, but lately I’ve been feeling less confident and it just gets to me.

        Since discovering your site about 6 months ago, I’ve shared it with lots of friends. Your message that real women with real lives can find fun ways to express themselves with fashion is terrific.

    3. Hi Beth,

      I’m in a similar boat (heelspurs combined with the aftermath of dislocating my big toe combined with an old ankle injury and now apparently hip bursitis while I’m at it). I need orthotics to be able to NOT collapse in a heap crying every time I go up a flight of stairs.

      I’ve been really happy with Drew Shoes as far as things that are dressier and will still take an orthotic, but I don’t know how well that will work with your ankle.

      Do short lace-up boots work for you? I always liked that look with long flowy skirts. 🙂

      Also so glad to see Allie answer this, because it does feel like messed-up feet can be this total obstacle to looking pulled-together and it makes me very very sad.

  7. You ALWAYS have the best responses to reader questions! And, that’s one of the reasons why I ALWAYS enjoy your blog! Thanks, Allie!

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