The One Boot Style I Buy Again and Again, Plus, My New Go-To Easy, Smart Outfit

Hands up if you have that back-to-school feeling. After saying farewell to the summer via our heavenly supper club at Templeton Garden’s Pippin’s restaurant, I sure do, and I’m chomping at the bit to be granted some time off from parenting to give my wardrobe a seasonal changeover—not sorry for admitting that! Ahead of my most indulgent fashion moment, I’m spending time pondering my options, thinking about what I wear on repeat when autumn rolls around and where my mood is heading for the season. This helps me prioritise any new purchases, as well as dry-cleaning, repairs or alterations that need to be done, making the most of what I own and filling only the most essential gaps.

This newsletter is dedicated to the outfits and items that go the distance during these colder months, from the boot style that never lets me (and my chunky calves) down, to the new outfit formula taking precedence over dresses.

As always, you can find me at @hannahalmassi. x

Here's What I'm Obsessed With in September

1: I WON’T SHUT UP ABOUT: STRETCHY BOOTS

If you’ve been reading this newsletter from the start, you’ll know about my personal struggle with knee-high boots. I’ve always had small feet but thick calves, and this ratio means that knee-highs have never been my friend. I discovered one leather, zip-up pair that works (shout-out again to Realm), but otherwise, there’s a particular style I always go back to: stretchy suede-and-leather pull-on boots. The offering now is far chicer than when this kind of hybrid leather fabric was first introduced, and my collection includes styles from brands such as Whistles, Me+Em and Charles & Keith, all the way up to Prada, L’Autre Chose (a now-defunct French shoe label, which was so good) and Dora Teymur. If there’s a stretchy, chic knee-high boot out there, I will find it. I like that they provide a sleek finish for many outfits, working well with midi skirts and even under trousers.

Shop my Favourite Stretchy Boots:

2: UNDER THE RADAR: SKIRTS ‘N’ SHIRTS

Shh! Don’t tell my dresses, but right now, I only want to wear one specific outfit formula: skirts with shirts. There’s something grown-up and polished about wearing separates, and I feel you can add a little more personality to an outfit you actually have to assemble. This combo is ideal for the in-between weather days of early autumn, where you can pair a woollen skirt with sandals, for example, or a flippy summer skirt with some cool knee-high boots (now that you know where I like to buy them!). Typically “masculine” shirts help counterbalance the prettiness of a skirt and provide a smart option for office days. I recently bought a perfect pink shirt from COS and have my eye on a skirt from Róhe. I’m sure both would get plenty of wear in this format, as well as with other separates, such as jeans (the shirt) and knits (the skirt). Pictured are some examples I’ve worn recently: Farm Rio (the banana-print set), a Prada skirt with a COS shirt and an M&S Collection skirt with a Soeur shirt.

Shop Skirts and Skirts:

3: ASK HANNAH ANYTHING (about style)

“What are your favourite niche places to buy knitwear?”

Hannah says, Readers, you know I love a challenging question, and this one is certainly that! But, being the experienced editor I am, I have answers. If you’re looking to support small brands that prioritise great knitwear, here are six, and they’re all British!

1. & Daughter: Excellent for a chunky knit or trending colour.
2. Navygrey: The place to stock up on sumptuous basics.
3. Madeleine Thompson: My go-to for something with a bit of drama, like a cape.
4. Hades: For rebellious motifs and slogans.
5. Rise & Fall: Slouchy shapes with a designer feel.
6. Slowlove: Pure yarn knits for homemade feels.