Easy Shoe Choices for a Modern Mid-century Wardrobe

vintage shoes

Do you notice my blog's little tagline? Modern Mid-century Sewing and Style. I always wondered where people came up with those catchy slogan since all I could ever think of was "My sewing blog." Then the concept of "Modern Mid-century" just came to me! I thought it was perfect: I love sewing and wearing vintage patterns from the early 60s--that era we've collectively come to call "Mad Men"--but I really can't compare to some of the super dedicated vintage bloggers out there who do an incredible job of recreating past styles, some of them on a daily basis. I think of myself as having a modern style informed by fashion of the 50s and 60s: not Mid-century Modern, but Modern Mid-century.

Although I mostly talk about clothes here (sewing them, specifically), you can't go around barefoot! I've made a little round-up of vintage-inspired shoes for those of us who love our full skirts and shift dresses of the 50s and 60s but don't dress full vintage every day. All of these shoes can be found easily and are adaptable to everyday wear and more authentic vintage looks.

Mary Tyler Moore as Laura Petrie in ballet flats via
1. Ballet Flats: The simplest choice. Ballet flats are so popular now that they don't scream "retro" by themselves, but paired with a vintage or vintage-inspired dress they look lovely, or channel Laura Petrie and wear them with cigarette pants! I currently have pairs in brown, pink, and red, and I like to have two pairs of black flats in my closet: a nicer pair (this year's purchase) and a beater back-up (last year's "nice" flats) that I wear to go out to the bar or a concert.

2. Block Heels: Even though Salvatore Ferragamo didn't design the "Vara" until 1978, this block heeled pump epitomizes the mid to late 60s to me--you want to keep them pretty low for a more vintage look. This is a silhouette that is hard to do really well and a lot of block heels just look clunky to me, but I love my one pair of Varas (my wedding shoes). I also just like block heels because you get some height and a little more comfort than a kitten heel or something similar.

Jackie Kennedy in Navajo Sandals via
3. Jack Rogers Sandals: The iconic Jack Rogers sandals are a good choice for a casual 60s vibe. At least in my part of the world, these sandals are everywhere, and commonly spotted with another classic item also popularized by Jackie Kennedy, the Lilly Pulitzer shift. "Lilly and Jacks" is a go-to combination for Southern girls, so unless you want to look like a sorority girl (which is fine, I am one #chioforlife) I would amp up the retro hair and makeup. A bouffant and winged eyeliner would not be out of place here; that's how Lilly Pulitzer wore hers!

Audrey in socks and loafers via
4. Penny Loafers and/or Saddle Shoes: Not everyone in 1965 was wearing Mondrian dresses and white patent go-go boots! Just about every fall I find myself inspired by the "Ivy League" look. Think plaid midi skirts and borrowed-from-the-boys preppy classics like button-down oxford shirts and cable-knit sweaters. For this, I love penny loafers (Bass's weejuns are classics) or saddle shoes. I wear my loafers sans socks all year round, which is not very "historically accurate" I don't think.  I find saddle shoes slightly harder to style than loafers or flats; they're a more distinct "look," but I always get compliments when I wear mine. (There's an interesting article about Vassar girls and the origin of this style here, and I'll have to write a blog post about this favorite of mine at some point this fall!) Bonus shoes that can also fit into this category: white keds sneakers.

5. Espadrilles, either flats or wedges: Popular since the 40s, nothing is quite so summery than an espadrille in either a wedge or a flat version. I prefer wedges, and navy blue fabric is more versatile than black if your summer clothes skew toward nautical like mine do. Who wants to wear black in the summer? Not me!

So there you are, my top five easy shoe choices for your "Modern Mid-century" closet. All of the shoes I picked are easy to find in stores (at least in the US) and can easily adapt to a full-on vintage day or a more casual look.

Lastly, I am totally of the mindset that you should buy the nicest version of a thing you can afford, and take care of it to make it last. I had a cheap pair of penny loafers a few years ago, but they didn't hold up very well, so when I bought new penny loafers, I got Cole Haan. They are so much nicer than my last pair, and I got them at a Nordstrom Rack (I think, it was years ago) so they weren't exorbitantly expensive. Same goes for boots: I have a pair of Frye boots I bought three years ago (the not particularly vintage-looking Melissa--as I said, I'm a sorority girl) and I'm about to get them resoled; they should last me for ages.

What do you wear with your vintage-style clothing? Have any shoe recommendations for me?


p.s. i got a shopstyle account, so you can see my little shopping widget down below. i'm going to try to use it to link to accessories like shoes in my outfit posts. let me know what you think--annoying? convenient? 

Shop this look via ShopStyle in the widget above.  These contain affiliate links, which means I get a few cents (at no cost to you) if you click or purchase. 

allie J.


  1. Love this post! I feel lucky that I can make clothes just as I like them, but I feel shoe-making is a frontier I'll never cross! Ballet flats and boots are my go to - ballet flats if I'm feeling sweet and demure and chic; my thick-soled lace-up boots if I want to make my ensemble a bit more modern and edgy. It's funny how much a pair of shoes can change up your look!

    1. There are a couple of bloggers who have done shoe-making classes but I'd rather buy mine and have more time to sew!

  2. Block heels! I love that style but had no idea what they were called. You just solved a big mystery for me. :)

    1. Happy to help! Currently if I do a search for "block heels" I get a lot of sandals with block heels rather than pumps but I think that's just the season :)

  3. 60s shoes are my fave!! actually all shoes are! i love the block heel look from the 60s, i have quite a few pairs that I've bought mainly from ASOS which are all adorable and cute! its very hard to get original 60s shoes in size 10/11 for my giant feet so i always have to buy new. There was also that one time i got a pair of shoes custom made from Milk and Honey, but their gone now and the company that took over them, don't have the block heel option and are terribly expensive! but at least i got what i wanted when they were around :)



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