Style Guide: Comfortable and Stylish High Heels

November 2, 2015

As a blogger with a main focus of ‘wear-to-work fashion’, it is probably not surprising that the one question I get asked more than anything else is what heels are comfortable enough to wear to work. So, today I am bringing you a Guide To The Best Heels.  And by “best” I mean most-comfortable while still being fashionable.

I’ve sorted the guide into three price points, to make sure there are heels for every budget. I also give you my own personal opinions and ‘coles notes’ (if you will) on each.

I hope you find this guide helpful! I saved the absolute best heel for last. Trust me, you need to check out this comfortable shoe! *happy dance*

Also – I will do my best to update this guide every couple of months to ensure that the shoes profiled are still available for purchase.


Before we get to the guide, I wanted to briefly talk about why I feel qualifies to write such a guide. If you are a regular reader of LLB, you know that I am always in heels. I actually only own one pair of flats. Because I am predominately a courtroom lawyer (ie. I don’t sit at a desk during the day) I am very used to spending 8-10 hour days in heels and often (according to my fit bit) walk over 10,000 steps in them. So, when I tell you a pair of heels is comfortable, gurrrrrrl, you better believe I have put those things through the ringer in testing said comfort! Alright, enough of me talking, let’s get to the guide:

The Most Comfortable (Best) High Heels:


Splurge ($300+):

1) Paul Green “Suzy” Pump – $319

A crowd favorite, these are considered to be some of the most comfortable designer shoes. They do have a chunkier heel (which is not my personal favorite look) but for comfort, they can’t be beat!

2) Manolo Blahnik “BB” – $595

The BB pump is renowned as being one of the most comfortable designer pumps. As an added bonus, this pump comes in a number of colors and patterns. One day I will own this pump. #shoegoals.

Affordable ($100-300):

1) Naturalizer “Anna” Pump – $150

I just got these and the cushion sole make such a difference! These are well worth the price.

2) Sam Edelman “Hazel” Pump – $120

I have these in black patent, nude and black suede because I just love the fit in the toe box. I would say though that these are a bit on the narrow side throughout the length of the foot – so, excellent if you have narrow feet, but not the best choice if you don’t.

3) Michael Kors “Flex” Mid-Heel: $100

The flex aspect of this pump creates an insole that is far more comfortable than the average heel. I have both the mid & high heeled heights as I love having the option between wearing high or lower heels every morning.

4) Michael Kors “Dorothy” Pump: $100

This higher version of the flex heel provides the same insole comfort with added height for those who prefer it. The only downside to this heel is I that with wear, the toe “wrinkles”; leaving a crease in the leather at the toe. It’s a bit strange, but not a deal breaker.

5) Cole Haan “Vesta” Pump: $180

Another great shoe because it comes in a number of colors, so once you decide you like the fit, you can stock up! I haven’t yet tried these pumps, but I have heard from multiple readers that they are very comfortable so for that reason I am including them. I do know from personal experience though that in general that Cole Haan shoes are great for comfort.

6) Blake 12-Hour Pump: $118

This shoe from Banana Republic was specifically designed, as the name clearly implies, to be comfortable for 12 hours of wear. I found this shoe needed a bit of breaking in (it felt stiff and therefore not that comfortable in the toe box the first few times I wore it) but after 3-4 wears this became one of my favorite pairs of heels. I actually plan on picking it up in some of the soft colors for spring!


Budget Friendly (under $100):

1) Calvin Klein “Gayle” Pointy Toe Pump – $95

These pumps are simply beautiful. Such a gorgeous, classic shape. I love that they come in so manycolors as well. These have comfort padding in them and so,especially for the price, are a truly great heel!

2) Naturalizer “Natalie”– $98

Naturalizer is known for their focus on comfort – especially when it comes to the insole and general shape of a shoe. This classic looking pump is their version of a work friendly comfort heel – and they definitely did a good job! I have been told by a few readers that this is their personal favorite shoe.

3) DexFlex “Jeanne” Pump– $30

These are the best cheap pumps you can buy. At a payless price tag, but with workmanship to create a comfortable insole and shape. Every woman should have a couple pairs of these in the closet (or under your desk .. where I like to keep a spare pair!) These are great for those days whenyour feet just need a break.


Currently on SALE:

1) Vince Camuto “Kain” Dress Pump – on sale for $98! 

edit August 11, 2017: These are my new favorite every day pumps! I bought them last week and just wore them for the first time today. Even as brand new shoes they were comfortable enough to get through the whole work day! I do find them a bit tight though so if you are between sizes I would size up a half size (I did).

2) Cole Haan “Air Juliana” – check Ebay, etc. 

I saved the best for last. YOU MUST GET THISSHOE IF YOU CAN. You may not know, but way back in2010 Cole Haan paired with Nike to introduce the Nike”air”concept into their heels. What this oh-so-heavenlycollaboration created was some of the most comfortableheels ever made. The collaboration ended in 2012 (sadly)but you can still find some of the “Air” shoes if you scourthe internet. The Juliana’s are my personal favourite because oftheir timeless look, but the Air Chelsea’s and Air Tali’sprovide the same comfort, if you like their look and can get yourhands on them.



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