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The Comfiest Shoes I Own

Helllooo from an *over-indulged in way too much fun over the last 5 days* Jess. ?

We got back from Montana yesterday (we had a 6am flight and had to get up at 3:30am ?) If you missed it, I was there for our best friends’ wedding–two of not only the most important people in our lives but at the top of the “funnest people we know” list–it was a raging good time full of our amazing group of friends, lot’s of late nights and way too many beverages, but it will hands down one of the best highlights of our lives.

The first part of the trip, the entire wedding party (and significant others) rented out an entire lodge, and then after the wedding we moved to rent out two gorgeous ski in/ski out condos at the base of the mountain. 

I am now paying for that fun, because I have one day to work and re-pack before I head off to Phoenix for a Beautycounter conference with Blair at the crack of dawn on Thursday. ?AM I CRAZY? Yes. But I’m also so excited for this upcoming weekend as well despite my stress levels being quite high. ?

Anyway–speaking of lot’s of travel, I get so many questions on comfy shoes–which obviously, are ideal for travel, but the older I get, the lower tolerance I have for uncomfortable shoes in everyday life as well. You too? Good, because today I’m rounding up my comfiest pairs of shoes for ALL seasons and all weather! ??

The comfiest flats: 

Gucci Brixton Loafers

Gucci Brixton Loafers

I get a LOT of questions on my Gucci loafers–I can confidently say that yes, they are worth every penny. Neal got these for me for Christmas a few years back and they are one of my favorite gifts ever. ❤️

I think you will have them until the end of time, they are a beautiful, classic staple that is exceptionally well-made. They also happen to be one of comfiest pairs of flats that I own–they are truly the most buttery, soft leather and they don’t require any breaking in. I have the Brixton loafers–they are technically convertible (i.e. you can fold them down into mules in the back) but honestly I’ve never worn them that way because I like them better the normal way and I don’t want to wear down the backs! 

Sizing: I wear a US 8 and went with the 37 1/2 (European sizing) and they fit perfectly. 

Sam Edelman Loafers 

Sam Edelman Loafers 

Whenever someone asks for my favorite gucci dupes, I tell them Sam Edelman’s pair–both the Lorraine or Lior Lorraine loafers are tough to beat–(the only difference is that the Lior has a twisty horsebit and Lorraine has the more traditional horsebit). I have them in leopard but they have traditional black, brown, and just about every other color you can imagine too. I think Sam Edelman is probably my #1 most worn shoe brand of all time. Everything they make is great quality, stylish, and importantly–always comfortable! Run true to size. 

See more ways I style both the leopard and Gucci loafers here

Steven Greece Slides: 

[one-half-first]Steven Greece Slides[/one-half-first][one-half]

Steven Greece Slides


THESE SANDALS. I own them in so many colors and they are truly the best.  I got mine when they first came out a couple of summers ago and they are still my absolute favorites. They look like Hermes, and are only $79!

I often get asked how they compare to Hermes. I don’t know because considering how much I wear my sandals into the ground, Hermes slides do not feel like a smart investment for me personally–but my guess is that no they do not feel as high end as Hermes. They’re $79! Let’s be real! BUT they are real, soft cowhide leather, they don’t rub or require breaking in, and truly, the comfiest slides ever, and I don’t usually think slides are comfortable. I even wore them all day walking all around Capri. I could not love a flat sandal more. Run true to size. 

See more ways to style the Steven Greece sandals here

The comfiest heels:

Halogen Demi Heels 

Halogen Demi Heels 

You have seen me wearing these on the blog and instagram a lot lately, for good reason. I’ve said it about 10 times now and I’ll say it again: I typically find one pair of new seasonal heels and I wear them into the ground for the year. These are going to be that pair. They aren’t just stylish, but they’re super versatile, they go with everything, and they are best of all–comfortable! They are made of nubuck so they’re very soft (and don’t dig into your toes) and the perforated material is great for keeping your feet cool when it’s hot out but for those times when it’s chillier, you’ll be glad for the extra material as well! They’re a really great transitional heel! Run true to size. 

See these shoes also styled here, here, and here

Sam Edelman Yaro Heels 

Sam Edelman Yaro Heels 

Speaking of running shoes into the ground–this pair is another one! I’m pretty sure all my friends have at least one pair of these heels in various colors. They really are the best shoes for weddings (whether you’re in one or just attending one). I love them especially in cork because they are neutral but add a great textural element to take your outfit up a notch! Run true to size. 

Because I know someone will ask–comparing the Yaro sandals (and the Carrson sandals below) to the Halogen sandals–I don’t think you can compare them. They’re just different! I think the Halogen sandals are more interesting, but the Yaro and Carrson sandals are more versatile simply because they can be dressier (i.e. worn for a wedding, whereas the Halogen ones cannot). If you’re looking for strictly comfort, go with the Halogen sandals because the heel is wider and lower. 

Steve Madden Carrson Heels: 

Steve Madden Carrson Heels

Most recently worn in my What to Wear to a Spring Wedding post! The Carrson sandals are basically an identical shoe to the Sam Edelman version above–I think they’re pretty interchangeable. For some reason I think the heel feels higher on the Steve Madden version but the descriptions both state 4″ so it must be all in my head. ?I’ve had a couple different pairs of these over the years (my other pair is a suede blue which is sadly no longer made) but I have always loved them! These run true to size. 

Sam Edelman Hazel Pumps 

Sam Edelman Hazel Pumps 

Another pair of heels I have worn forever–I think these might be my oldest pair of shoes that I own. We’re talking like…at least 6? Maybe 7? Years. (Which is why mine are an older version). Another Sam Edelman pair–the Hazel Pumps–which, I’ve turned so many people onto over the years and always get dm’s of thanks over, haha! They are the truest definition of an elegant, classic pump–I love them in suede–they are my go-to date night shoe when its cold and they are perfect for any work setting as well. (I have run through many an office in them late for a client meeting ?) These run true to size! 

See more ways to style the Sam Edelman pumps here

Everlane Day Heels 

Everlane Day Heels 

Ah, the heels I NEVER shut up about–Everlane’s Day Heels. I never really know if I should put these in the “heels” or “flats” category because they’re kind of in-between. I love them SO. MUCH. If you’re the kind of girl who can’t stand heels purely for comfort’s sake (or because you’re always on your feet for work)–these are going to change your life. They are so comfortable I have walked MILES in them in one sitting. I brought them to Italy. I’ve walked from Michigan Avenue to Wicker Park in them in the summer. They are truly unparalleled. Sizing: go up 1/2 size if you’re in between! 

See a bunch more ways to style the Everlane Day Heels here

The comfiest boots and booties:

Everlane Day Boots 

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How to wear ankle boots to work


So, now that you know about my Day Heel obsession, it should be no surprise that The Day Boot also tops my list. If you don’t believe me, I wore these walking around the cobblestone streets of Portugal, back to back, for multiple days, and they were perfect. They are truly the chicest booties, and because they are the same structure as the Day Heel (just with more leather, obviously, haha) they are the comfiest pair of booties I own. They come in lot’s of colors, too, but I am partial to the beautiful tan! 

Blondo boots

The Comfiest shoes - Blondo boots

Come on, did you really think any shoe roundup of mine wouldn’t include Blondo boots?! I know they’re probably a little out of season now with winter coming, but I wanted to mention them anyway in case you’re traveling to a cooler climate or happen to be perusing this post several months from now. 

Blondo makes the best booties and booties ever. They are ALL waterproof, all super comfortable, and all very high quality. The ones I’m wearing above are again, years old, but very similar to the Velma pair that is in stock now! I would highly recommend checking both Nordstrom and Lord and Taylor’s selection–both have a lot to choose from! 

More reading: How to wear Over The Knee Boots 12 Ways 

The comfiest sneakers: 

Tretorn Sneakers 

Tretorn Sneakers 

I loveeee love love love these sneakers. They are my new favorites–feel like soft slippers (no break in!) and are minimalistic and chic enough to pair well with cute dresses. They run true to size and come in lot’s of colors, but, you know me–old school and classic, I love the all white version! 

See more ways to style these sneakers here

Allbirds Sneakers 

Allbirds Sneakers 

Last but CERTAINLY not least– Allbirds! I have them in both dark grey and light grey and much to my surprise, I actually wear the dark grey a lot more. They are made of 100% wool and are machine washable. They also feel like slippers, and I love the way they look! I’m not a super sporty kind of girl, so they are the right mix of classic and sporty for me. If you need a shoe that is supportive but still cute, these are going to be your thing! 

I’ve been asked a few times lately if I had to choose between the Tretorn and Allbirds, which would I choose, but that’s basically asking to compare an apple to like…a coffee machine. ?

There is very little cross-over with what I wear each pair with (I guess, other than with jeans and tshirts).

Allbirds are comfier, chicer, more minimalistic stand-ins for your trainers. You would rarely be able to pull off Allbirds with a pretty feminine dress without looking like you were commuting somewhere and planning to change your shoes eventually. (However, I have worn them with something like a super casual t-shirt dress!) I love them for running errands, traveling, etc–times you want to be really comfy (i.e. feel like sweats, but actually look put together). They’re sportier, but still classic, you know what I mean? 

Tretorns are more versatile, and while super comfy, they are also more fashion forward, so you can wear them with a girly sun dress and not feel frumpy–whereas that would be much harder to pull off with Allbirds. I hope that helps, haha! I promise to post a “what to wear with Allbirds” post soon!! 

Was this a helpful post!? I hope so!! Whether you’re looking for comfy travel shoes or everyday shoes, you cannot go wrong with any of these pairs!