Shoe shopping blows more than a Dyson hand dryer, particularly for the large footed among us ඞ. They either don’t exist in your size, are sold out, are too narrow, aren’t long enough, or are simply just like finding a needle in a haystack. The most important thing is patience. You only need ~2 pairs of shoes to make 95% of outfits click and once you have those it’s really just a matter of time and personal taste.

I fell into the trap of only sticking with ‘gender neutral’ options for shoes like converse and other sneakers. It felt like I could never find anything in my size and no matter which store I went to, they always had nothing, or in the case they actually did, it was a special order online that I would need to pay for before it even got to touch my feet. 

My current shoe collection has been pretty slow building over 5 years, as there are few shoes I like to wear that are comfortable and well suited options for year round. I live in a place with harsher winters, meaning the mandatory winter boots are on my feet everyday for about 5 months of the year. This leads me to wearing my other shoes as much as I can, and making many mistakes.

First, you need to think of what shoes are going to be appropriate for the activities you actually wear them for and match your clothing. You aren’t going to wear thigh high suede boots to law school, nor are you going to wear sandals in a chemistry lab (I would hope).

There are 4 main shoes I think you need in order of importance

1. A comfortable, neutral color sneaker
2. A casual-ish black dress shoe/boot
3. A fancy heel/boot
4. A pair of work/hiking boots.
   • Optional sandals instead if you’re living that princess lifestyle where you don’t need working boots.

Here are my own pairs of each. You may notice a common theme of them pretty much all being black. Black goes pretty well with everything and won’t make my shoes stand out, which could clash with my clothing.

4 pairs of shoes is pretty reasonable, but you may find yourself wanting more if you might run into trouble. Shopping for a more diverse range of shoes is going to be difficult but the most important thing is finding your real size!

What I mean by this is using shoe conversion charts EVERY SINGLE TIME YOU PURCHASE A SHOE. European sizing is gender neutral, so always go by this if you can. France and Italy (usually just Italy) have different sizing systems that run a bit smaller than EU sizing but will usually specify ‘FR’ or ‘IT’ in their sizing. I am generally an EU 43 or 42. 

You should also ALWAYS aim to try shoes on in person. Even if you are buying shoes from a brand where you know your size already. The exception is if you are buying a new colored pair for shoes that you already own.

As an example, I bought these running shoes and sandals within a few hours of each other. The size of the running shoes is a 44 EU and the sandals are a 41 EU. If I hadn’t gone in person to try them, they would BOTH be the wrong size.

When buying shoes, I always go for the slightly larger of the two sizes if that option is available because you can’t make a shoe bigger, but you can artificially make your foot bigger by wearing thicker socks! This trick has saved me more times than I can count and even a small difference in thickness is enough to make a shoe go from uncomfortable for long periods of time to perfect. It’s especially important for shoes that do not have half sizing. (So having to pick between a 9 or 10 instead of 9.5)

The 1st core option is the neutral sneaker. Having a comfortable pair of sneakers is important because you need to be able to just live life without having to worry about what you’re wearing all the time. There are plenty of options, from white leather sneakers to black running shoes. I would go for something black because shoes get dirty pretty quickly. Pick a ‘low top’ sneaker for this as ‘high top’ sneakers are a much more sporty look so you won’t be able to wear them to an office unless it is a more casual environment to begin with. 

I usually just opt for them when I know I’ll be doing a lot of walking, or am simply too lazy to put on a real outfit.

The 2nd core option is the ankle boot. When it comes to a ‘casual dress boot’, there are many options to choose from. If you have a hard time finding a size that fits you, going for a Chelsea boot is a solid option. Ankle boots, aka booties, are a more feminine silhouette but may not be so easy to find in every size. They both serve the same function, but a Chelsea boot will be a bit more casual because of the stretch fabric compared to something entirely leather. 

Here is a demonstration of how versatile they can be!

For the 3rd core pair, opt for a dressier kind of heel/boot. That can either be a higher heel, or something made of a more ‘luxurious’ material like suede. There’s plenty of ways to go about this one. I personally don’t like having my feet exposed that much so I opted for boots.

Here are a few outfits I would elevate with a dressier shoe.

The 4th core pair of mine is actually a pair of men’s boots. There’s nothing in particular about them that screams ‘MEN’ apart from maybe their overall size. The small heel also differentiates them from being a standard work boot with flat soles. Realistically, I wanted a sturdier pair of boots and this fit my criteria at the time.

If you don’t need a pair of work boots, get a pair of sandals instead assuming your climate allows it.

The only pair of sandals I have, and the only ones I’ve needed, are these black Birkenstocks. They go with skirts, dresses, and pants (although they will dress down the bottoms).

While it may be tempting to get many shoes that you like but ultimately only fit a certain kind of special occasion, don’t buy more than one pair like this. Getting your sparkly pink 4 inch stiletto heels is as far as you need to push it for over the top heels, you don’t need them in every color of the rainbow as well no matter how tempting it is. 

I have this pair of heels I bought simply because they fit me at a time I wasn’t finding any other shoes that fit me. I have only worn them twice within 4 years. I wouldn’t be able to justify more high heels until I have cycled through these. This is more of a personal issue because I don’t find myself wanting to be 6’7″, but if don’t let it stop you from wearing them around your home if it makes you happy.

If you have one silhouette of shoe that you really like that’s perfectly fine! I really like higher shaft shoes like ankle boots or high top sneakers because they make up the distance for pants that are a bit short.

You just need to make sure the shoes you get are not practically identical save for a few minor details. Different colors and materials are a good reason to get a new shoe even if it has the same shape of one you already own. 

I have a pair of suede and leather ankle boots, which may not be too different from each other other than the material, but that makes them different enough that I feel comfortable purchasing both. 

A more dressy boot can simply be a material change. Suede is a great option for this as it is difficult to take care of and therefore is considered a fancy material for shoes. Higher heels fit this category well and the more of your skin you show, the fancier the shoe. 

“Mens” shoes from more fashiony brands will also be a bit more on the feminine side assuming they’re ‘fashion forward’ (stupid buzzword for ‘progressive’ and not stuck in the past). They will have a greater extent of larger sizing but keep in mind they don’t really make a lot of these so sizes can go quickly. You’ll also probably be paying a bit of a premium in many cases compared to what you may be used to, but they will also be of higher quality. Shoes are absolutely worth investing your money though as you will always be wearing some kind of shoes as a part of your outfit unless you’re a part of homo-erectus. 

These sneakers are also men’s shoes. But there’s nothing gender-norm wise that prevents you from wearing them, they’re just a different vibe. 

Avoiding the pitfall of uncomfortable shoes is also super important for both your wallet, and feet. If you can’t stand wearing the shoes for more than a few hours, don’t. Permanently damaging your feet for the sake of pointed toes means you’ll end up needing clown shoes to compensate for the poor choices you made just so that your feet may recover. I own quite a few pairs that aren’t comfortable so I never wear them for more than hour at a time. 

Also a pro podiatrist tip I learned is that you should avoid leather shoes in the hot or humid weather as they trap heat and moisture, making your feet swell a bit and making it much easier to get blisters on your feet. So focus on filing out core options with comfortable and high quality shoes is an investment that pays for itself in very little time.

Now if you do want more shoes that are more optional to own, riding boots or knee high boots are the most solid option by far. They can be worn year round and when worn with shorter skirts or dresses they really add a feminine feel without relying on shoes like flats or heels. I have 3 pairs, the last of which was the first women’s pair of shoes I ever bought. Granted, I never wear them because they don’t fit me very well but the excitement at the time clouded my judgment.

They also pair well with skinny jeans for all my millennials still out there wearing those, you get a pass on skinny jeans  if you wear them together.

Now you may notice I am biased towards boots, and that is because boots are the most feminine and typically most comfortable option for shoes that come in larger size ranges. Flats can be a good option, but generally they squeeze your feet into a more narrow shape because they resemble ballerina flats. So, if your feet are particularly wide, they won’t conceal that very well (if that bothers you).

Boots can be worn in nearly every scenario that flats can and more, so I recommend making them a priority.

Depending on what you do for work, I would avoid buying a lot of sneakers. I have 11 pairs of converse but rarely wear more than 3 pairs. At the time I purchased them, I worked in a much more casual work setting and I fell into the trap of buying nothing but converse because trying to find other brands with my size was too frustrating. Much like my collection of hoodies in every color, they rarely get much use.

Now out of my entire shoe collection, here are all of the shoes that are mostly collecting dust on my shoe rack. There are a few exceptions here but not many.

A final thing to consider as well is how our feet might change if we take HRT in some cases. The cartilage between our bones will compress further when there isn’t as much testosterone, leaving your feet to shrink a size or even 2 in some cases. Because of this, it’s best to avoid any expensive shoes for a few years, as tough as it may be. It isn’t a guarantee this will happen though, as nice as that would be.

I have purchased a lot of shoes, and you can almost perceive the rest of my style just from the way I purchased shoes. They really are that important to your wardrobe. But to review,

• Always try shoes on in person
• Have a high quality core rotation of shoes
  • Choice paralysis is real!
• Materials differentiate how fancy a shoe is classified
  • It’s much easier to justify a new pair that’s a different material rather than a different color
• Avoid uncomfortable or ill-fitting shoes, they’re not worth it
  • Some “men’s” shoes are not that masculine looking so don’t be afraid of looking in that section if your size is particularly rare
• Have a variety of styles! Locking into 1 kind of shoe will limit what you can form looks around
  • Boots are the most versatile though 🙂