Ally Shoes Penny Loafers: A Classic, With a Slightly Preppy Twist

This blog post is a paid for advertorial in collaboration with Ally Shoes.
Items that were received as PR product are marked with an asterisk * 
Read the disclaimer about affiliate links & PR products here. 

Ally Shoes have just released their new Penny Loafer – a slightly different direction from what we’ve traditionally seen from the brand, with a more masculine, preppy feel that still feels very Ally.

Ally loafers* (use ‘VEEFLATS10’ for 10% off; sz US 6.5), Venroy knit top* (sz M), Nobody Denim jacket* (sz S), Uniqlo trousers – AU link; US link (sz S, in-seam length altered to 64cm), Status Anxiety sunglasses, Oroton bag*

Many of Ally’s styles lean toward the more classic, feminine end of the spectrum (which is exactly what first drew me to the brand). The Penny Loafer, however, brings a slightly more tailored, borrowed-from-the-boys energy. That said, it’s still very much a classic penny loafer – clean lines, timeless silhouette, and the kind of shoe that slots seamlessly into an existing wardrobe. The styling possibilities really are endless.

I opted for the Moxie Mocha pair, a beautiful chocolate brown suede that I already know and love from Ally Shoes. I also own their kitten heels in this same shade, and they’ve become my most worn heels from the brand. There’s something about this rich brown that feels softer than black but just as versatile.

Ally loafers* (use ‘VEEFLATS10’ for 10% off; sz US 6.5), Venroy blazer* (sz S), lululemon t-shirt* (sz S), Sezane skirt (sz 36), Parisa Wang bag*, Oliver Peoples sunglasses

One of the first things I noticed about the Ally Shoes Penny Loafers is how soft they are. If you’ve tried the brand’s City Loafer, you’ll know that style has a bit more structure to it. In comparison, the Penny Loafer feel a lot softer and more flexible, which for me is a huge tick.

Comfort has always been one of the main reasons I’ve gravitated toward Ally Shoes. They originally came onto my radar for their comfortable heels for work, as is well documented on my blog. Their shoes are podiatrist-designed, with thoughtful comfort features built in – something I’ve spoken about before, and something that genuinely sets the brand apart.

L: Ally loafers* (use ‘VEEFLATS10’ for 10% off; sz US 6.5), Venroy blazer* (sz S), lululemon t-shirt* (sz S), Sezane skirt (sz 36), Parisa Wang bag*, Oliver Peoples sunglasses; R: Ally loafers* (use ‘VEEFLATS10’ for 10% off; sz US 6.5), Venroy knit top* (sz M), Nobody Denim jacket* (sz S), Uniqlo trousers – AU link; US link (sz S, in-seam length altered to 64cm), Status Anxiety sunglasses, Oroton bag*

Even with a more structured, traditionally masculine silhouette like the Penny Loafer, that comfort element is still very much front and centre. The penny loafers feature a cushioned insole, built-in arch support and a flexible construction, which makes them particularly comfortable for all-day wear — and, in my experience, a big part of what keeps me coming back to Ally Shoes.

Ally loafers* (use ‘VEEFLATS10’ for 10% off; sz US 6.5)

The result is a shoe that looks polished, feels comfortable, and works across a range of outfits — from tailored trousers, to denim, to flowy if you’re leaning into that slightly preppy aesthetic.

Ally loafers* (use ‘VEEFLATS10’ for 10% off; sz US 6.5), Sezane shirt (sz FR 36), Uniqlo jeans – AU link; US link (sz 26)

If you’re interested, you can take advantage of my discount code VEEFLATS10 for 10% off.

Ally loafers* (use ‘VEEFLATS10’ for 10% off; sz US 6.5), Alemais shirt* (sold out, sorry!), Uniqlo trousers (sold out, but here’s a similar pair of linen trousers), Bellroy bag*, Status Anxiety sunglasses

And because heeled styles were what first put Ally Shoes on my radar, I also wanted to call out a couple of my long-time favourites: the kitten heel and the lower block heel. Both feature a walkable 2″ / 5cm heel, and I genuinely consider these my everyday heels for the days when I want a little extra height without sacrificing comfort.

Kitten Heel:

Ally heels*, Scanlan Theodore t-shirt (sz S), Scanlan Theodore jeans (sz AU 8), Dragon Diffusion bag, Oliver Peoples sunglasses

The Ally Shoes Kitten Heel is one I reach for regularly – polished, understated, and genuinely comfortable. It’s the kind of heel that works just as well for the office as it does for more casual styling. You can read my dedicated review here.

Lower Block Heel:

Ally heels*, Scanlan Theodore t-shirt (sz S), Scanlan Theodore jeans (sz AU 8), Status Anxiety sunglasses, Saben bag*

For another style well documented on my blog, the Lower Block Heel offers a little more stability while still maintaining that elevated feel. Another easy, everyday option that doesn’t compromise on comfort.

If you’ve been curious about the Ally Shoes Penny Loafers, this new release feels like a very natural – and very wearable – addition to the lineup. I hope you found this to be helpful.

As always, thanks so much for stopping by!

P.S. You can have a read of my other reviews of Ally Shoes styles here.

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