The Best Winter to Spring Transition Shoes

Happy Monday, friends! I hope you all had a good weekend. I keep getting questions about the best spring transition shoes, so I thought I’d post a roundup!

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If you live in the southern United States, you probably wear your “spring transition shoes” all winter, but this time of year is tough for those of us in colder climates. The days are getting longer, it feels like spring is near, and we’re tired of our boots, but it’s too chilly yet to break out the sandals.

I’ve been getting a lot of questions lately about when to put away the boots and what to wear while we wait for warmer temperatures to arrive, and my answer is always, “loafers and ballet flats!”

And these days, the fashion sneaker trend adds some variety to the mix.

Spring Transition Outfit with Fashion Sneakers

I get it — not all of you are experiencing weather conducive to bare ankles just yet, but many of us are! If you aren’t quite there yet, just tuck this post away for future reference. I promise, spring WILL come… eventually!

So, what’s trending for spring transition shoes this year?

Pointy Toe Flats

Transition Shoes for Spring 2020: Pointy Toe Flats in Leopard Calf Hair

Pointy toe flats are making a comeback this spring, and while they may not be quite as comfy as ballet flats, I like the air of sophistication. They also tend to be more flattering because they visually elongate the line of the leg.

The J.Crew leopard flats pictured above have been a favorite of mine for a few seasons, and they’re finally on sale! They have such a flattering silhouette, and they add polish to the most basic outfit. They seemed stiff at first but broke in very easily. I recommend sizing up half to accommodate for the pointy toe.

I also have the Linea Paolo pair with the notched topline (the pink ones in the picture at the top of this post) and they’re comfortable and flattering as well. They come in a bunch of neutrals and bright hues, depending on your preference. These run TTS ; I have the 8.

Shop Pointy Toe Flats for Spring:


Mules are having a moment right now, and I’m not mad about it. I especially like the loafer-inspired mules like the ones pictured above. A traditional loafer can skew a little too masculine for my tastes, but the backless loafer mule is tailored with a touch of femininity.

I’ve been jonesing for those white Gucci Princetown loafer mules for ages, but I just can’t bring myself to spend that much, so I settled for the Sam Edelman Laurna mules. They look nice, but they’re a little stiff.

Everlane came out with The Day Loafer Mule just a few weeks ago, and I ordered it immediately. It is so good, you guys! I love the low profile, and the leather is soft and supple. The sole is flexible, and they way they’re designed, they actually stay on the foot. In fact, it’s so good that I already ordered another color. Definitely my #1 spring transition shoe this season! You can see them in Friday’s Try-On Haul.

STYLE TIP: Mules looks best with cropped and ankle length jeans and pants.

Shop Spring Mules:


Loafers are a classic style that is also trending at the moment. We’re seeing everything from super preppy menswear-inspired penny loafers to casual drivers, and everything in between.

My current fave is the Everlane Day Loafer because of the low profile and how soft and flexible they are. The Sam Edelman Lior Loafer is more of a classic style with the horsebit hardware, and they are deceivingly comfortable! They have a cushioned footbed, and the leather is super soft.

If you don’t care for the menswear vibe, we are also seeing a lot of the more feminine pointy-toe loafer right now. And of course, smoking slippers and driving shoes are classics that never go out of style.

Shop Spring Loafers:

Fashion Sneakers

Veja Esplar white leather sneakers are one of my favorite transition shoes for spring 2020

Fashion sneakers definitely sticking around for a while, and this is one of my favorite ways to make that spring transition chic and effortless. There are tons of options out there right now, so choose a style that works for you and your wardrobe.

I’m a huge fan of my Veja Esplars, and the new Everlane Court sneakers are supremely comfortable and very much on trend.

For a less spendy style that’s also trendy, check out these Amazon fashion sneaks.

They don’t have to be white either. I love my Vince snake print slip-ons.

I’ll be updating my Fashion Sneaker Review next week, so stay tuned for that!

STYLE TIP: When wearing trendy sneakers, it looks best to leave your ankles exposed, which means no visible socks. If you can’t bear to go without, try a no-show sock.

Shop Fashion Sneakers:


Eileen Fisher Lee Espadrille Flats

These are sort of a loafer, but I’ll give them their own category because I love espadrilles during the springtime! I mean, I wear them all summer long, but they are particularly nice this time of year becasue they usually have a closed toe, but the jute sole makes them summery.

The leather espadrille flats I’m wearing above are suuuuper comfortable. I was really impressed by these last summer, and I can’t wait to bring them out again! The leather straps add interest, and help keep them on your feet. Eileen Fisher is a sustainable brand, too, if that’s important to you. These also come in black and taupe.

Shop Espadrilles for Spring:

I hope this post helps make your winter to spring transition a whole lot easier!

For the Pinners…

The best spring transition shoes for 2020, including product links and style tips!

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photos: Alison Cornell

Join the Conversation

34 thoughts on “The Best Winter to Spring Transition Shoes

  1. I decided to “suck it up” and wear my leopard flats (bare ankles) even though it was in the 30’s when I walked into work today. Ditched the winter coat as well, at least for today. Supposed to be in the 50’s, so I decided to go for it. I just needed a break from booties and boots and winter coat. It is still early for spring in New England, so there will be many days I will need to wear booties (which I love – thank you, Jo Lynne, for turning me on to them.) My husband bought me a great pair of sneakers (for walking) yesterday in a blush color. Very springy, and I love them. Bring on some warmer days!

    1. The sneakers sound cute, and YAY for leopard flats! When I went to college in Boston, I wore ballet flats right into the winter my first year, and I couldn’t understand why my feet were always cold. My friends had to tell me to get boots. You can take a girl out of the South, but . . . 😂

  2. Does anyone actually own something like #3? I love the look but everytime i try something like this on they just don’t “walk well” for lack of a better statement….what i mean is they don’t seem to bend in a way that doesn’t keep the heel from coming off with every step and i don’t have this problem with ANY other style shoe – just the ones with this type of heel base. Thoughts? Also there aren’t any in the picture above but i also like the sandals with just the one wide strap across the toe end of the shoe but when i wear this style i sound like a horse clomping, clomping, clomping – shoot i don’t make that much noise when i wear actual flip flops….maybe i just walk “hard/loud”

    1. I have a pricey pair of YSL espadrilles that I love, but I do find that a lot of other brands are stiff and hard to walk in. I haven’t tried the Sam Edelmans, but the reviews seem like they may be okay. Sounds like they run narrow tho.

  3. Great post!  Over the weekend I pulled my cold weather footwear out of my closet.  Even though I haven’t gotten all of my warm weather shoes out of the attic yet, it feels good to have the others out.  When I saw how many pairs of shoes I have up in the attic, I was totally shocked. I need to carefully assess each pair to decide if they should be in my closet or be donated!  I hope that you didn’t freeze during the photo shoot this morning!  It was 34 when I got up, but it’s supposed to get up to 70.  The wide temperature swing makes outfit selecting a bit challenging.  Have you and Paul decided whether or not y’all are still taking your May trip?  A road trip for the family event this month could be fun!  Have a fabulous day!

    1. Yes, that is a wide swing! We are just taking the wait-and-see approach right now. Our trip is paid for, so there’s nothing to lose by waiting. If the situation gets worse, maybe we can arrange to postpone the apartment and excursions. I don’t think they will give us refunds. My plane tix, I believe, can be canceled… but we shall see.

      1. I hope that everything settles down and things return to normal so that y’all can go!  There are more cases of it showing up in Georgia now, but none real close to us yet.  With Larry being a 73 yr old cancer patient with a compromised immune system, we have to be extra cautious.  There are several events coming up that we’d like to attend, but we can’t be in large crowds.  🙏🙏

        1. Yes, you all will definitely need to take extreme precautions. It has hit around here already, and some schools are closing. It’s only a matter of time until ours does, I’m sure.

  4. Love those leopard flats! But I’ve just never gotten into ballet flats of any kind – they make me look short and stumpy. I do like some of the new loafer styles, though. May have to look into some of those for work.

    1. They can, depending on your body type and all. I do love a good ballet flat – they actually help my long, slim feet not look so long. 🙂 I think you might prefer a loafer.

  5. I have such a hard time with transition footwear. My feet are narrow and I have high arches. Ballet flats, loafers and mules just Don’t work. I’d love a pair of espadrilles but so far every pair I’ve tried on are too wide or too high a heel for everyday running around. Any suggestions? 

    1. My feet are also very narrow with a high arch so I can sympathize with you. There must be a solution that does not involve “walking out of the shoes” or “sliding out the front end” LOL

      1. I think the only solution is finding out which company makes narrow shoes, or stick to oxfords & runners. For that reason, I love booties and have them in several colors, both leather & suede. 
        I was buying Timberland hiking boots that were narrow. Annnnd, they just stopped making them this year as the market for narrow is too small. Really?!  😢 I hunted down a pair and had them shipped ASAP. 

        1. I also have narrow feet. Naturalizer and Bella Vita are two brands that carry narrow sizes but styles are limited. Ugg and Dr. Scholl’s slip on sneakers tend to run narrow per reviews and they have worked for me.

          Jolynne your work navigating through the styles and how to wear them is so appreciated and has been extremely helpful. Thank you!

          1. So glad to hear that, Rosemary. Thank you! And thanks for sharing some brands that run narrow. I used to need narrow shoes, but somewhere along the way, I was able to wear medium. I have a wide toe box and narrow heel – an awkward combo!

          2. Naturalizer does have narrow but I find they don’t always have the latest. I’ve never heard of Bella Vita but will goggle them today.
            I find lace up sneakers fit the best. Slip ons…well…slip.
            Thanks for commenting. 😀

    2. Yes I would look for the shoes that run in narrow sizing. It will probably cost more in the specialty stores , but will be worth the fit. I had a AAA foot width and high arch until I had children, then went to being able to wear the M width in stores, still have my high arch  ( I still have to watch the styles though ) as some can still be too wide and with a narrow heal I walk out of them ( that’s when I add a heal grip) . I know the shoes that have a buckle around the ankle and open toe aren’t for me as I walk right out of them …

    3. I have flat feet with a wide toe box and narrow heel. It’s a pain at times! But I have never dealt with the high arch, so I’m not sure what to recommend. Glad to see others chiming in!

  6. Yes during the transitional time I’m so sick of boots.. I’ve been wearing my white sneakers and slip on sneakers. It’s a little early for mules and sandals well that will happen in June lol… looking forward to your fashion sneaker review 🤗. Today it’s 44 but tomorrow could be in the minus temps again. Who knows? I’ll just take it while we have it:)

      1. Yup I am.. yesterday was a beautiful 44 no wind and today it’s -6 with the windchill but reads plus 2 as a high. (34). Last year we had no spring… the nicest day was the day of our daughter’s wedding when it was sunny and 80. Other than that it was cold and damp.. I’m hoping that because we had colder temps earlier in November that we might see a spring but it’s a season we often miss:) so far getting 30-40’s in March is nice as odd as that

  7. Are the white Converse tennis shoes (I think they’re called Shoreline with the back elastic) out of style? I bought mine two years ago. Loved them and found them comfortable. But a few times last year they would hurt the backs of my ankles after awhile. Anyone else have this issue?

    1. Was wondering the same. Also bought mine 2 yrs ago and haven’t worn a lot. Was thinking since white sneaks are in, I might get by with these another year.
      Haven’t had the back of ankle issue….

    2. I wouldn’t say they’re out of style, just not really trendy at the moment. My 14-y/o wears hers a few times a week, not that we want to dress like a 14 y/o, lol, but I don’t think they’re out of style.

  8. I can’t keep a loafer on the back of my foot to save my life. My foot is wider across the front and narrow in the back. Do the ones with elastic in the back, like the Everlane Day Loafer, work better for a narrow heel? One saving grace is that I can wear, and am actually most comfortable in shoes without any arch. So I just bought some pointed toe Mary Janes from Old Navy for $15 that are very cute and quite comfortable for me. Crazy, I know. 

    1. I don’t know… I just don’t really get them that dirty. I do have some light colored ballet flats that I wore so much, they got worn looking, and I just replaced them. But I got a couple years of very regular wear out of them.

  9. Great round up! I actually find the Steve Madden pointy flats much more comfortable than my Tory Burch round toe flats because they allow more room for my bunions! The regular flats tend to cut just at the bunion so I can never wear them for long while I can walk the dog etc in the point toe- just go up a half size! 

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