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