The Curious Case of Cobb Hill

As most of you have noticed in my more recent outfit posts/reviews, I’ve been gravitating towards Cobb Hill shoes. I’m here to tell you, internet – there’s a reason why.  And that reason is: THEY ARE RIDICULOUSLY COMFORTABLE.

See, I do not get along with heels.  Which is odd, because in the late 90s and early 2000s I wore 2 1/2 to 3 inch platform boots every day.

Chunky platform 1990s boots
I swore by boots just like these for probably about 7 or 8 years.  No kidding.

But as time went by, I gravitated more to flats, especially in my work wear.  Ballet flats, pointed-toe flats, any and all flats.  And at some point, my feet decided no more heels.  I tried re-integrating heels into my life in the form of kitten heels, chunky heels, platform heels – no dice.  My feet could not take them.  I thought I’d be doing flats for the rest of my life.

I first heard about Cobb Hill in my Facebook dress groups, and seeing them on a lot of ladies who came in town for DivaCon last year.  The Aubreys in particular are fan favorites among the group, and I can see why: they have the perfect 1940s vibe with their t-strap and chunky heel.  They pair nicely with the vintage-inspired styles from Trashy Diva and other retro repro companies.  But that wasn’t why people were buying them.  They were buying them because they swore up and down that they were some of the most comfortable shoes on the market.

I have a hard time believing hype about comfortable shoes.  I’ve had people swear up and down about shoe styles only to find that my foot hates them.  I have a pair of adorable BAIT oxfords that look fantastic – until I stand up.  Then all my toes slide forward in the shoe, smashing against the front of the shoe, and I end up barely being able to walk back to my car. I’m talking straight up hobbling, y’all.

After hearing rave after rave about them on Facebook, though, I finally decided to give them a try.  I found a brand-new black pair on Poshmark for about 40% off regular price, so I snapped them up.  When they finally arrived at my house and I tried them on, I was OBSESSED.  I first wore them out with my Micheline Pitt Carmelita dress and instantly began searching on Poshmark for other colors.  I now have three pairs of these shoes – one in black, one in tan, and one in pewter.

The Aubrey has a 1 1/2 inch heel, which is perfect for a little lift without feeling like you’re teetering.  They have a steel shank in the shoe for stability.  They’re made out of leather and have plenty of cutouts on the toe and heel of the shoe, plus they’re open on the side, so my feet don’t feel overheated.  The footbed is non-slip and has cushioning in the heel and ball of the foot.  I have worn these shoes all day during a con with little to no aching at the end of the day, and no blisters.  THAT is a major test of strength for a shoe!

Other Cobb Hill styles

With my closet of Aubreys growing larger, I’ve been looking on Cobb Hill’s website so I can try out some different styles.  Check out these awesome styles that I’d love to add to my closet!


Cobb Hill Angelina shoes
Cobb Hill Angelina in bordeaux

The Angelina mimics the look of the Aubrey but without the totally open sides and toe.  As much as I love my Aubreys, wearing them in the winter is not really possible so I’d love to get a couple of pairs of these to add to my closet for colder months, or in places where open toes aren’t possible.  I’ll probably stick with my black and brown, but this bordeaux color is really tempting!


Y’all, I love a good oxford.  Like if I’m really going full Agent Carter 1940s daytime look, an oxford is where it’s at.  The Rashel has that great sturdy Cobb Hill heel and steel shank.  I wish it came in brown, too!  I’d love to have these basics in my closet.


Summertime is here and espadrilles are super hot this season (or at least everyone’s telling me so).  Most of the sandals in my rotation are flats, but there’s some times that a heeled sandal will just provide a little more fanciness to an outfit.  I love the Kairi suede x-strap with the velcro adjustment, and that blue is so pretty!

What do y’all think of these Cobb Hill styles?  Would you add them to your wardrobe?  Comment below and let me know!

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