Boot Season

The boots I'm turning to this A/W

The flip-flops have been packed away and the boots are out

Knee High Boots Over Dress 2025

It felt like the right moment for a boot rundown, the pairs I’m reaching for now and the shapes setting the tone for the season ahead. Boots (along with a good coat) are two of the most important wardrobe investments for A/W.

Get them right and they’ll instantly elevate your outfits – and last for years. When it comes to choosing the right style, start by looking at your wardrobe and what you wear day to day. For me, that means three: an ankle boot for daily wear, a flat boot for ease, and a knee-high when I want to elevate things.

Once you know what shapes actually work with your wardrobe, it becomes simple.

Boot Edit Substack Over Dress 2025
  1. The Ankle Boot

An ankle boot fits best with both my outfits and my lifestyle. I live in straight-leg or baggy jeans, and a slight heel with a pointed or rounded toe works perfectly with those shapes. I also reach for tailored trousers a lot – a sleek, close-fitting boot sits neatly underneath and keeps the proportions right.

I make sure my jeans are long enough to cover the top of the boot so no skin shows between the hem and the boot, a small detail that instantly makes the look feel more considered and modern. I tend to stick to black leather for longevity. A straight-leg jean, low-heel boot and a great coat will be my go-to uniform all season.

 

Ankle Boot Edit 2025 Substack Over Dress
Ankle Boots Over Dress Substack
  1. The Chunky Boot

The practical pair, the ones I reach for on off-duty days with relaxed jeans, joggers or leggings. I’m drawn to brown lace-up or zip-up styles this season; they feel softer than black but still grounding. Perfect with an oversized knit or long coat for an easy, pulled-together look that still feels lived-in.

Combat Boots Over Dress 2025 Substack
Brown Boots Over Dress Outfit
  1. The Knee High Boot

The pair I reach for when I want to elevate an outfit. I usually wear my knee-high boots under a longer silk or maxi pencil skirt, so the shape shows subtly through a slit as I walk. I’m not keen on them over jeans or leggings, I prefer a cleaner line. I do, however, love a flat, chunky knee-high in summer with a shorter dress – it balances the proportions and adds that grounded contrast I always look for.

Knee High Boots Substack
Knee High Boots Over Dress Substack

A Chelsea boot with a mid-heel is my go-to this A/W. Mine are from Arket or look to Dune or Toteme for a similar style

Arket Boots Over Dress

The Boot Edit

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