Last updated on December 27th, 2021 at 11:43 pm

What are transitional shoes?  You actually already know.  They are the shoes that you struggle to find twice a year.  The first time it happens is when it’s not quite spring, meaning it’s too warm for boots and too cold for sandals.  And the second time is early fall, when the opposite occurs. 

For me, personally, I find it hard to find shoes I really like this time of year.  I’ve historically not wanted to invest in shoes that I’ll only wear for a short period of time. But I found that this year has been a little bit different.  Since we’ve all done a “pandemic shift” with our wardrobe this year, I’ve found myself more interested in fun, casual shoes.  These are the shoes that look good with leggings and jeans, since that’s mostly all I’ve been wearing.  Here are my top picks for casual transitional shoes.  

Full disclosure:  I am only 5’3”, so wearing flat shoes is a little tough for me.  So I typically try to find something with a little bit of a heel if I can.  I also have a wide foot and if you do too these shoes should work well for you also.  Here’s a little tip on wide shoes — Target has a lot of wide shoes on target.com that you can’t find in stores. It’s worth checking out.

The Picks

Speaking of Target, I found these cute little gems on their target.com for only $22.99. Because they are tie-dye and very trendy, I didn’t want to spend too much.  They could end up being a one-season shoe, but for $23, why not?  They only come in whole sizes – I am typically a 7.5 so I sized up to the 8 and they fit great.

Everyone needs a classic white sneaker.  What I love about this Adidas shoe is just the touch of “metallic copper” on the heel. Adds just a little bit of fun.  I found these on dsw.com for $59.99.  They are also offering them this year with a bright green and burgundy heel accent. The green/white also come in men’s and kids, if you want a matching family set!

Next up is probably my new favorite pair of transitional shoes – a great combination of both style and comfort.  Technically a training shoe, it’s my go-to “run errands in leggings” shoe.  Made by New Balance, they are very comfortable and I love the houndstooth pattern.  Houndstooth is both on-trend and a classic pattern, so I can see me being able to wear these for quite some time. I got my pair at dsw.com for $59.99.  They have limited sizes left at DSW,  but they are also available at shoecarnival.com for $64.99. 

I have a Leopard wedge sneaker that I love that I bought a few years back.  My shoe is no longer available, but I did find this one that is very close to what I own.  Leopard print makes for great transitional shoes — they are classic and season-less. I found this Caslon pair on the Nordstrom Rack website for $49.97.  A bonus here is that they are water resistant – perfect for the upcoming “April showers”.

I also like a d’Orsay flat – they work well for my wide feet and I think they are just a little bit more stylish than a traditional flat.  Target sold a great d’Orsay flat that I own for several seasons but it has been discontinued.  I found this Catherine Malandrino one that I like (and may need to order!), also at Nordstrom Rack.  It’s a great transitional color and the perforated nubuck leather makes them perfect as both spring and fall transitional shoes.. Best of all they are on sale for only $39.97. 

As I mentioned, I have a hard time wearing flats because I’m a little on the short side. I usually like a little bit of a heel to elongate my look.  But I decided to go looking for a flat that I could try to love.  Here’s what I found – these adorable Steve Madden pointy mules in a fun plaid print.  Available also in solid black, leopard and snake prints. They have just a teeny heel and the pointed toe also helps to elongate the foot. They are $49.97 on nordstromrack.com

Now that you’ve got your shoes, check out Jen’s blog post on her favorite loungewear and create the perfect outfit!

And let me know what you think!  Did you find a new favorite in this collection?