To boot:

An uncomplicated guide to boot styling

We’ve reached the melding of many seasons. Mercifully, the least complicated of them all might be ‘boot season’.

Boot styles don’t generally change drastically from season to season. So if you didn’t trash your boots walking in salty slush last year (that’s a me problem), then you’re probably sitting on some great options. So here’s a guide to wearing the boots you probably already own!

These boots are noisy AF and rattle like a set of keys but I love them! Anine Bing biker boots (or go for TikTok’s current obsession, the Frye boot, or Target’s version here) Z&V sweater, Ozma skirt, Jenn Lee bag

The Golden Rule of Ankles:

Wondering where your pants should hit in relation to your boots? The answer is almost always “ankle bone”. This especially applies to round and square toe boots (and now that I’ve called it out, I promise you’ll notice it when you see it done correctly).

The Khaite Marfa: most perfect specimen of a square toe boot. Strikingly similar version here, or go for an even more walkable version here

My beloved Target Chelsea boots from last year are a copy of these Ganni boots (currently on sale, comfy and weather proof).

Ankle rule applies here too:

Stacked heel boots from Amazon (a copy of these) and a cute waterproof option here

No time to tailor? Be like this chic woman I saw in Paris and roll your jeans.

Learn the rules, then break them:

Ankle rule doesn’t apply in the case of long baggy jeans & trousers.

Allison Bornstein

breaks this down in a video, but know that “pointy boot” has entered the chat:

Pointy boots elongate your legs in a baggy pant. Wearing this Jcrew sweater (a favorite), Agolde jeans (these run big), and Anine Bing boots - similar option here (code ABBY30 for 30% off until 11/24).

The long and tall:

There’s no cozier winter look than tall boots paired with a dress or skirt. Cold? Add tights. The gold standard is always Wolford. I’ve also had good luck with these opaque tights at Target and if you want to be extra toasty go with fleece lined tights like these or these.

The right boot does ALL THE WORK. Pair tall boots like these from Khaite (or similar from Madewell ) with a sweater dress like this from Alex Mill (leave the bottom buttons open) or a mini skirt and sweater

I got these riding boots from COS to wear with holiday dresses

Tall boots from Dolce Vita paired with a flowy maxi dress from Natalie Martin

Boots need a comfort boost? Try these footpads or these if you get a boot blister

Of course you know that Black Friday is HERE and some of the deals are stellar; Anthropologie is offering early entry today with code ABBY30 and includes some of my most loved pieces like the Donni kick flare pants, Citizens jeans (these and these) and the best black jeans (code ends 11/24).

Todd Snyder is 30% off site wide with code BLACKFRIDAY30 starting 11/23 (you know who is getting this and this)

And Madewell is 30% off site wide with code MADEBETTER

The deals abound but don’t go overboard - there’s nothing worse than staring at a pile of stuff you got on sale, hate, and have to return.

‘Til next time!

xo

Abby