Wardrobe From Scratch, Part 6: How to Choose Shoes

It’s been a hot minute since I first wrote the Wardrobe From Scratch series 3 years ago.  (THREE?  OMG!)  Anyway, one thing I didn’t cover was SHOES!  And one of the questions I get asked most often is from people who are rebuilding their wardrobe and looking for guidelines on shoes.  What are basic shoes to buy when starting out?  What are your must-have shoes?  How many should I start with?  How do I choose colors?  How many shoes should I start with?  What kinds should I get?  HELP–it’s overwhelming!  

Today we’re finally talking about it!  It’s taken me so long to answer this question because I didn’t think I had much to offer–I mostly wore tan flats.  It was pretty simple in my mind, and kind of silly for me to just tell everyone to buy tan flats.  Haha!  But as I thought more about it and heard more people’s shoe questions, I began to understand why shoes could be confusing.  There are a lot of things to consider: which types of shoes will best fit your lifestyle, how to choose among the billion styles of shoes, determining which colors to buy of which style of shoe, and so on.  All of those considerations can be overwhelming, so let’s talk through a few of them!

If you are not building a wardrobe from scratch, please leave a comment with your top must-have shoes and your lifestyle or style to help give others ideas of what their shoe arsenal could be like.  Thanks in advance for your input!



Before looking at any kinds of shoes, I would review what you determined as your lifestyle needs from Part 1 of WFS because that will tell you what kinds of shoes you need.  For example, if you work in an office most days out of the week you will need different kinds of shoes than someone who chases kids most days of the week.  Don’t worry, you don’t need to know what kinds of shoes will fit these activities yet.  We’ll get there.  For now just clarify your lifestyle needs.
My lifestyle looks like:
  • casual work environment 4-5 days/wk
  • super casual activities (errands, park, or playtime with toddler) 3 times/wk
  • dressy-casual activities (church, work events) 6 times/month
  • dressy events (weddings, parties) 2 times/mo
YOUR TURN: What types of activities do you do, and how often do you do them?

Types of Shoes

With all the different kinds of shoes out there, I’ll list a few basic ones here and which kinds of lifestyle activities they’d be best for.Below each category I’ll also show a few examples to give an idea of what’s possible.  The prices range from $25 to $130, though I tried to only show more expensive ones from trusted brands.  Some of these come in multiple colors that are not shown in the widget.

Flats – Can range from everyday casual to dressier, from ballet flats to D’orsay flats to oxfords to boots to sneakers.  But no matter the style, they will be comfy and easy to walk long days in.

Wedges – Whether closed toed, peep toe, or sandals, I love wedges for being between casual and semi-dressy.
They also tend to be easier to walk in than pumps because they provide more support

Pumps & Heels – Easily dress up any outfit.  They can instantly make an outfit polished, professional, or dressy.  Most of my heels are very simple pumps (shown in the image at the bottom of this post), but there’s a huge variety of designs for heels.  I stuck with showing simpler ones, as I imagine if you are someone who finds shoes overwhelming you likely wouldn’t be ready to get loud or fancy heels yet.

Sandals – These can come in all heel types listed above (flats, wedges, heel).  I find they are usually better for casual wear or dressier events (with a heel…which I just realized I didn’t show any of, but oh well…) and harder to incorporate to office looks, especially if it’s a business environment.

Boots / Booties – These also come in all heel types and are a girl’s best friend in colder months.  They come with all sorts of shaft heights: ankle height booties, then mid-calf, knee length, and over the knee.  They can also range from casual to dressy.  See the post on choosing the right ankle boots HERE.

Also included here should be any weather appropriate boots you need here, such as rain boots or shoes for snowy commutes.

Sneakers – These can look sleek and stylish for everyday wear, not just going to the gym.  You just have to find the right ones!  Below are examples of great everyday sneakers.

There are definitely more than these, and each of these categories has its own nuances, but hopefully this helps you narrow down options.


Types of Toe Shapes

Then, for each of the styles listed above the shape of the toe can make a big difference in the style of the shoe.  Some basic toe styles are:

It’s up to you, your lifestyle, and your style preferences.  I prefer pointy toed shoes for a sharper look when I’m trying to look professional or a little more dressed up and rounder toed shoes (usually almond toe for me) for more casual vibes.  Though I know plenty of people who don’t like pointy toed shoes, they can really help elongate your leg line, especially under trousers where feet tend to get lost.  Almond toes are kind of an in-between of rounded toes and pointy toes and are a great alternative if you don’t love pointy toed shoes or are worried about your feet sticking out too much but still want the sleeker line of a pointed toe.

To decide on colors, I would review which neutrals and colors you determined for your Starter Kit Wardrobe.  (See Part 2 of Wardrobe From Scratch on choosing colors HERE.)  If you’re just building your shoe collection virtually from scratch I recommend sticking to mostly neutrals because they are the most versatile.  And then, because my style board shows that I love a pop of color, I personally would add a couple of bold colored shoes as well.  (See Part 1 of WFS on determining your style HERE.)

I started writing a lot on this, but then I stopped myself, remembering that most of you who’ve asked me about shoes have expressed feeling overwhelmed by them.  Talking about materials was making it even more overwhelming.  There are many types of materials shoes are made of and also the type of finish on the shoe.  I don’t even want to list examples because that’s where it could get overwhelming!All I’ll say is I pay most attention to whether or not I want the shoe to be shiny, matte leather, suede, or like a canvas type of material.  For some reason I’m very drawn to suede for pumps as opposed to patent leather.  I feel a little less corporate in a suede heel, and it helps me wear my pumps in more casual settings.

Starter List of Shoes

Once you’ve determined your lifestyle and colors we can create a starter kit list of shoes that will work for you!  A very easy thing to do if you are starting out is to choose one shoe from each category under “Types of Shoes” in one of your neutral colors.  If you know you won’t need or wear a shoe in one category, ignore that category.  If you want to choose more than one from a particular category, go for it!  If you want a couple of neutral shoes and a colored pair in the same category, that’s fine too!  Seeing shoe types and how they function differently in your life will at least give you a starting place, but mold and change the list to make it work for you.

For my lifestyle, my personal starter kit looks like this:

Shop Shoe Options:

Swipe through the widget below to see shoe options.  Click one to shop.  If I own them or have tried them, I wrote notes underneath each item for sizing and comfort.  SIZING: I’m usually 8.5 to 9 in shoes.


I listed shoes for all seasons, but if you want to narrow it down even more, just focus on shoes you will need for the current season.

I do have more shoes than this, but if my entire shoe wardrobe were limited to this list (plus shoes for working out or necessary weather appropriate shoes for commuting*), I would be satisfied.  That’s just to say that you can have a shoe wardrobe of around 10 pairs, give or take a few, and I believe most of your shoe needs will be taken care of year round.  Now, if you have a shoe addiction, that’s a different story…but then you wouldn’t need this post to begin with!  🙂

(Remember, if you live in a snowy/rainy climate, include weather appropriate shoes when thinking of shoes in the Boots section!)


Which of these are on your list of shoe staples?

**For all 6 parts of the Wardrobe From Scratch Series, click HERE.

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