Shoe Wardrobe Essentials

This was a reader question from Becky. She wanted to know:

I’m an avid reader of your blog, and I especially enjoy your fashion advice. Your ‘Wardrobe Essentials’ were really useful for me as I find I always skip buying the boring basics and go for the one-off pieces that really catch my eye but don’t go with anything in my wardrobe… anyway I followed your advice and haven’t had any “I have nothing to wear!!” moments for a while now. And I seem to have saved a lot of money too… 

I would love to see your advice on Shoe Essentials – I’m not good with shoes and never seem to buy practical pairs that go with lots of different outfits. So if you’re looking for a new topic to cover, it would be great to have some advice on shoe must-haves, please!


I did 10 essential shoes that you should own, and sorted them by seasons, and even offered a couple of extra options.

The seasons are as follows (just in case, not trying to insult your intelligence)






So, here goes!

Things to consider


I am not going to tell you that you MUST buy 3″ heels for your fancy heels or you must only wear flats to save your feet.

This is totally up to you.

If you can pull off 3” heels every single day in all of your shoes, by all means go for it (but I don’t recommend that because podiatrists will tell you that it’s awful for your feet!).

Personally, I stick more to the flats, or at the most, 2” in heels. And I like spiky heels too, not chunky ones, so I tend to be careful about how many shoes in my closet have heels especially since I walk a lot.


Don’t cheap out on things like Winter Boots and your Everyday Flats. Those are the ONLY TWO I can really recommend if you’re on a budget to NOT cheap out on.

I really suggest leather for most of your shoes because leather breathes and it stretches, as well as molds nicely to your feet to be super comfortable.

They are what you use the most, and what you want to have as very comfortable. The rest, can be of lower quality since you won’t be wearing them as often, or sludging through snow and ice and hoping not to fall on your pretty little butt.


Not all of the shoes here might fit your lifestyle. This is just the broadest range of essential shoes I could come up with while appealing to a wide range of women.

If you don’t feel like you’re a knee-high boots, or ballet flats kind of girl, DON’T BUY THEM IF YOU WILL NEVER WEAR THEM. What’s the point?

For me, this entire list is what I would use on a regular basis, and I (naturally) have more shoes than I actually “need” for a complete shoe wardrobe, but if you are on a budget, don’t ever think that you have to buy every single pair right away.

Take your time, buy the most important ones first, buy quality and make sure you love them because they are supposed to last you at least 3-5 years if not longer.

I’d call it investment shoe shopping, but investments make you money, and these shoes don’t actually generate dividends ($$), so that term is misleading and I refuse to call them investments out of principle as a PF (Personal Finance) blogger 😉

Knee-high boots

I would totally suggest that knee-high boots be strongly considered. There are plenty of cute knee-high boots out there in high heeled forms, or even in a flat form. Don’t go for a winter-style, knee-high boot that’s flat. That’s your winter boot. This pair of knee-high boots is meant to be casual, a bit dressy, and fun for specifically SPRING and AUTUMN.

You should be able to wear them with skirts or with skinny jeans tucked into them. I like the idea of a knee-high flat riding boot for myself, because it’s dressy enough to match a lot of the skirts and pants that I own, without being too wintry in the sense that it’s sheepskin-lined, with heavy duty rubber bottoms, and are waterproof to the max. You know what I mean.

The best, would be a boot that can go either casual or dressy. A thinner leather boot, that hugs your leg, with a slight bit of a heel if it’s comfortable would be your best bet. You can go for something a bit fun, and totally impractical for winter (this is where I’d have a 2” heel), because you aren’t going to be walking on ice or snow, you’re really showing off the boots here, and giving yourself an option to wear tights with boots, and to make your skirts last longer than the summer or late spring.

Winter Boots

This is where you should really think about a thick, warm comfortable, sweat-wicking, low-heeled, rubber-soled, waterproof boot. If you live in a city like Montreal the way I do, you will NEED waterproof boots.

Alternatively, you could buy rainboots and wear really thick winter socks. Just a thought. Not much more I can say on this, but try and keep ‘em cute, but remember: fashion is NOT FUN without function.

Your winter boots may look cute, but if they don’t keep you warm and dry, what’s the point?

Everyday Flats

I like ballet flats for this. I know many people don’t, or they feel their feet are too big for ballet flats, or whatever else. But I think they’re great and they look casual enough to wear them with jeans, and nice enough that you could wear them with trousers.

You can also buy really pretty ballet flats with a bit of detail, like in a quilted bronze, that is still a neutral colour, but FUN because it’s a metallic neutral.

These are the flats that you wear almost every day (except for Winter of course). You walk in them until they have formed around your little toes (which is why I suggest leather), and you will pretty much live in them all the time.

If those everyday flats in ballet slippers are not your thing, you don’t HAVE to buy them, you can buy casual trainers instead and save the moolah on these shoes.

Black Formal Heels

*Winter with a cab

These are not only black heels that you can wear to work, but they are appropriate heels to wear to any formal event because they are:

A) Not too strappy
B) Not too high
C) Not too fancy
D) Not in some wild fabric like satin with a trailing silk ribbon that’s difficult to tie
E) Appropriate for all formal events/work

Sounds kind of boring right? Let me explain why a classic black heel is required. You can wear it to business meetings, funerals (I know, I know, but I had to say it), and to events that require you to be formal, but not sexy (I don’t know, maybe an awards dinner or something that’s stuffy and boring).

Black generally goes with everything, especially with almost any suit (actually all I think, even white or pale colours. It looks a slight bit odd, but it works in a pinch if you have to use them).

In this case, you can buy leather or you can buy in a fabric. Personally, I lean towards leather because it stretches and moulds. But whatever’s your preference.

Think: Classic and Formal, not Trendy and Fun. There are shoes that are appropriate for that.

Neutral Heels

*Winter with a cab

Know how I said that black pumps go with almost everything, even the lighter colours, even if it looks a bit odd? This is where if you have the cash, spend it wisely on a pair of neutral coloured shoes.

Personally, I don’t think that brown, navy, grey or taupe (please, no white!!) are the only neutrals out there. A neutral to me, can also be a burgundy red , a deep not shiny bronze or a deep pewter. Those colours compliment and look nice with a range of many colours and it looks pretty to boot while giving a bit of sass and personality. You already HAVE your formal black pumps!

Party Heels

*Winter with a cab

So now that you have your formal black pumps, your slightly more fun neutral pumps, this is where you can go HOG WILD.

Buy a pair of party heels. The sky is the limit here, but I do want you to keep in mind that these party heels have to work with your wardrobe.

If all you own is the colour blue for example, don’t buy blue party pumps. Buy them in a bright yellow satin with a bow or something. Make sure that whatever pair of party heels you buy, will be complimentary to your party wardrobe, and comfortable to boot.

Who wants to go out to dinner and dancing in 4” heels that look fantastic but hurt like hell? Be reasonable.


Kind of essential for a lot of cities. This could do double-duty as a winter boot (depending on how warm your winters are), and just wear some really thick winter socks and it could work for a warm, slushy winter.

Alternatively, if you live in a rainy city like Vancouver, then these are a MUST-HAVE for you.

If you feel like you can’t be bothered to spend the $50 on a pair of rainboots because it’s quite dry, hot and dusty where you are, then put the money to good use in another pair of shoes that you deem to be useful.


The choice is totally yours. When I say trainers, I mean shoes like those Puma or Adidas shoes you see. They aren’t REALLY work out running shoes from Nike or Reebok (those are Optional as not everyone works out and/or needs workout shoes).

No no, these trainers are like your everyday flats. They are more casual than a ballet flat, but just as cute with some jeans, and a white t-shirt and a warm cardigan.

It’s a shoe that you can throw on for activities that a ballet flat can’t quite fit because it may slip off easily, whereas a trainer can lace up and stay on your foot as you’re dangling it.

I am not sold on wearing these trainers with skirts, but I’ve seem some girls do it, so go for it if you can rock the look. Personally, these trainers are only for trousers or jeans. Period.


I am not talking about flip flops here. Those are an essential, but so are sandals. Sandals are NICE open-toed shoes that are great for the summer (think of the gladiator sandal) with skirts or with pants, but are not so casual that you can’t wear them to an event.

Who shows up to events in flip flops anyway? No one. But you also don’t want to go in closed toed shoes sometimes because it can get kind of hot and icky.

So the sandal is a nice option to that.

Flip Flops

The basics of all basics for me. I like those really foamy flip flops, but they suck for your feet or so my podiatrist says. So I tend to prefer the kind of classier flip flop that has a hard bottom, with a leather thong across the front between my toes.

You can wear them to the beach, out on a summer day or around to the grocery store.


You can always expand on a shoe wardrobe, but these are the 3 major areas that I think you may need if you wanted to spend more money to kind of bulk up your shoe wardrobe.

Running Shoes – Workout


This is if you work out a lot. But if you don’t, then MEH. 

I own a pair, but only because I used to work out a lot. But I use them for when I go hiking or when I go walking a lot and I don’t want my feet to get tired.

Not really required since you have Everyday Walking shoes…


Dressy boots


This is if you want to have casual flat boots that are knee-high and then have dressy boots that are knee-high, you just NEED to have two pairs of boots, don’t you? 🙂 

I have 2 pairs of boots because sometimes a casual boot just won’t work and you need something with a bit of a spiky heel….

I like having two options because a boot can’t be totally dressy and totally casual at the same time. It’s kind of hard.. at least, I’ve never found a boot like that.

Other types of sandals

This is for if you love wearing sandals. You can buy more sandals with heels, without heels, closed-toe sandals, open-back/slingback or many others. I could see someone having fancy dress sandals, flip flops and more casual sandals as their 3 types of sandals, but this is only if you really like sandals in the summer and you wouldn’t really use trainers or ballet flats.

About the Author

Just a girl trying to find a balance between being a Shopaholic and a Saver. I cleared $60,000 in 18 months earning $65,000 gross/year. Now I am self-employed, and you can read more about my story here, or visit my other blog: The Everyday Minimalist.