Here’s an easy guideline for boot wearers who like the idea of keeping their assortment minimal and versatile. The heel height, colour, pattern, fabrication and style integrity are to your taste, although I’ll make a few suggestions along the way. 

You’ll essentially need five pairs of boots, which sounds like too many for the minimalist wardrobe. But if you have a proper Autumn and Winter, as well as a cold Spring, wearing boots more frequently makes perfect sense. Note that this list does not include snow boots and rain boots. Also, tall boots refers to knee-high boots and mid-calf boots, while booties also includes ankle boot lengths. 

  1. Dressy Tall Boot: Heeled, knee-high boots in a neutral colour with a streamlined fit are extremely versatile. The heel can be as low as one and half inches but heels are a must for dressy boots. Wear them with dresses, skirts and culottes. Flop proof. 
  2. Casual Tall Boot: Go either heeled or flat. Riding boots, Fryes and biker boots come to mind, but any casual tall boot will work. They can be streamlined or slouchy, and ever so distressed. Wear them over jeans and leggings, or with skirts, dresses and shorts.
  3. Dressy Bootie: Again, a heeled version is best for a dressy look, but the heel can be low. A bootie that fits more closely around the ankle tends to look dressier, and is a more flattering option for those with dainty ankles. A neutral shade for this bootie type is a good idea. These days, you can wear booties with anything, which makes them even more versatile. 
  4. Casual Bootie: Cowboy boots, Fryes and Dr. Martens boots come to mind, but any casual bootie will work. The fit can be roomy and slouchy, and the leather distressed. As with dressy booties, you can match the casual version with just about any relaxed outfit. It’s merely a question of whether you like the outfit combination with a high vamped shoe. 
  5. Extra Fun Boot or Bootie: Go wild with this option. Choose any tall boot or bootie style that’s more daring, be it in terms of colour, pattern or design. How about a pair of floral or green snakeskin booties. Or a pair of flat studded over the knee boots. Or yellow embroidered cowboy boots. Or silver Go-go boots. Or three toned colour blocked booties. Or monster wedges. Anything at all. 

Remember that there is life after black boots and booties. Neutral can mean ANY neutral shade that is light, mid toned or dark. Also, those questioning whether they need dressy boots and booties when they lead a very casual lifestyle have a point. In that case opt for either a dressy tall boot or bootie, and double up on one of the casual options.

By all means purchase more pairs of boots and booties if you have ample opportunity to wear them. Also, if you’re just starting out with a new wardrobe, don’t feel that you need to fill out your complement of boots and booties all at once. Working towards your ideal wardrobe is an ongoing effort.

I love to wear boots and booties, and have many pairs because they suit my climate. I can wear booties virtually year round in Seattle and tall boots at least eight months of the year. This means that I have many more pairs than this complement suggests.