The Geek’s Guide to Picking the Right Shoes

You’ve asked for it, so now let’s do it: a geek’s guide to picking the right dress shoes!

The weather is getting warmer, and you may find yourself needing to put on a suit, or at the very least a shirt and tie (that hopefully we’ve helped pick out) and a pair of slacks, and head to a springtime event: maybe a graduation, or a wedding, or maybe someone’s just hosting a dinner party now that it’s not so cold outside that everyone just wants to shut themselves in and hide under blankets for three months.

So you have an invitation in your inbox, or worse, someone actually mailed you something so now you know you have to go and there’s no squirreling out of going or out of the fact that you’re going to have to wear something nice. Before you go into the attic and grab your Dad’s hand-me-down white wingtips with the airflow holes in the top, take a minute or two and read through this guide.

I promise, if you apply a logical mindset to the issue and take these tips to heart, I can help you show up in style, and with a little shopping around you won’t spend a ton of money on it either.

I know, I can hear you now: “How often do you actually look at someone’s feet? It can’t be that difficult to find a pair of shoes!” You’d be right: there are a lot of things you can get away with when it comes to formal and semi-formal footwear. The problem is that when you violate one of the bigger principles, it’s not that there’s a high likelihood that no one will notice, it’s that you’ve gone and created a situation where there’s a high likelihood that someone will notice.

For example, the old adage that your belt should match your shoes? Yeah – that’s an important one. If you haven’t heard it before, take it to heart, it’s a freebie. If you’re wearing brown or earth-toned shoes, wear a brown belt. If you’re wearing black shoes, wear a black belt. You can bend this rule if you don’t expect your belt to be seen, but since it’s pretty likely it’ll be visible from some angle, try to stick to it, okay?

That said, let’s dive into three specific suggestions you can take with you when you’re looking for a pair of formal or semi-formal dress shoes.

  1. Comfort Comes First

    The first thing you should do when you go shopping for formal or semi-formal shoes is get yourself fitted. I’m serious – I don’t care if you just bought a pair of Vans or picked up a pair of running shoes. See, it’s not that I don’t trust that you know what size your foot is, but….I don’t trust that you know what size your foot is.

    Really, when you go shopping for a suit, unless you’re hitting the thrift store (and there’s nothing wrong with that) someone will probably take your measurements to make sure the suit you buy fits you perfectly and falls the right way. The same thing should apply to any type of clothing that you expect to wear infrequently, or that you don’t buy Moncler outlet often. If you buy a pair of dress or business casual shoes every week, then you can skip this step: clearly you know your foot size and you don’t need help. But if the last pair of shoes you purchased were sneakers, and the pair before that were loafers, and the pair before that another pair of sneakers that you’ve now replaced with the ones you just bought? Get fitted.

    Making sure you have the right sized shoes will make sure that your feet are cozy and comfortable in what are clearly some of the most uncomfortable shoes known to man (with the serious exception being virtually every type of women’s shoes. Seriously gentlemen, cut the ladies some slack – heels hurt like no one’s business and any sympathy she shows you about your dress shoes is clearly a ruse to make you feel better.)

    The other benefit of making sure you get sized is that you can point out to the person helping you that, for example, the wedding is outdoors and you’ll be standing a long time (in which case you might buy a pair of insoles, and a pair of shoes that can accommodate them. See where I’m going?) or that the person sizing you can point out that you’re not really an 11 1/2, but an 11 1/2 wide, which can mean a world of difference in hurt versus comfort.

    Oh, and in case it needs to be said? Try on the shoes before you buy. Wear dress socks so you get a good feel for how they’ll fit on your feet when you need them, or ask for the nylon disposable try-on socks that virtually every store has.

  2. Consider The Need

    The next thing you need to remember, and maybe you should think about this before you go shopping instead of while you wander the stacks of shoes, is that different events call for different types of shoes. One handy rule of thumb to take with you to the store is that the darker black and more mirrored the shoe is, the more formal the engagement. (Clearly there are exceptions to this, like uniform shoes, which are almost always shiny at the least, and patent leather in some cases.)

    Some people like to say that brown shoes are too casual for any formal event and that you should stick with black. I don’t think I completely agree there, but I do think that most formal engagements will probably call for a black or charcoal suit, in which case you’ll want black shoes anyway. However, you can get away with some chocolate and mocha shades of brown shoes in gray or lighter charcoal suits, even if you’re headed to a wedding or a dinner party. Clearly you don’t want to head to a cocktail party in anything but black, though.

    Hopefully you’ll want to pick a pair of shoes that works in multiple situations. You know what I’ve said about multi-tasking pieces of your wardrobe. That may not always be possible if you’re buying shoes for a very formal affair, but if you’re headed to a friend’s wedding or a job interview, try to find a pair of shoes that’s sharp enough to make a good impression but also to wear when you land the job.

    The other adage that I want to dispel is that decorated shoes: the kinds with patterns on the top or wingtips or buckles are all indicative of casual affairs, but nice enough for business casual events or workplaces. First of all, I wouldn’t suggest any of them – with the possible exception of solid-color wingtips (I think they’re due for an ironic comeback, but only in the super-glossy black form, with jet black suits. That’s probably the only exclusion I’m willing to offer.) – mostly because I think that highly decorative shoes have fallen out of fashion regardless.

    Buckles, ties, and tassles were far more popular in the 70s and the 80s, but the more sleek, clean, and smooth modern lines of modern suits lend to a very streamlined appearance. If you look sleek and Moncler outlet smooth all the way down to your feet, where there’s suddenly a huge sterling silver buckle on your matte black shoes, you’ve gone and killed that streamlined look. Ditch it and go for a pair without them. Don’t get me started on brown shoes with tassles. Seriously. Cut it out.

    Ultimately? You can’t go wrong with black, but pay attention to the formality of the event and the shininess of the shoe. You can get away with brown in the right situation, as long as it doesn’t clash with your clothes. Speaking of the shininess of the shoe and clashing with your clothes, that leads me to my next point.

  3. Consider The Outfit

    While you consider the event that you’re planning to attend, you should also consider the clothes you’re going to wear to that event. Again, like above, not everyone has the luxury to pick a pair of shoes for every occasion, but there are some basics you should follow. Like I mentioned above? If you’re going to wear a belt – and you probably will with a pair of dress pants – try to match your shoes to it as closely as possible. This is another “can’t go wrong with black” moment.

    Even if you’re not wearing a suit and you’re just wearing a pair of slacks or dress pants, try to match your shoes to your pants, or go with a darker color. Yes, this is another “can’t go wrong with black” thing. Are you seeing a pattern yet?

    Very light brown shoes should be worn with colors that work with it – which frankly aren’t too many. Now you see why a lot of people perceive lighter shoes as casual shoes – you can get away with a bright brown pair of shoes or even cowboy boots if you’re wearing jeans, but if bright mocha shoes are peeking out from under jet black slacks, they’re going to attract attention. Like we said, the point is to make sure the adage holds true: no one should be looking at your feet specifically, and they shouldn’t be the source of attention. Your shoes should compliment what you wear, not stand out against it.

    If you’re really interested in adding some color to your shoes, I applaud you – there’s nothing wrong with being adventurous, as long as you do it intelligently, and I know you can be intelligent: you’re a geek! So remember this: Black shoes go with virtually everything, especially black, navy, charcoal, or gray pants. Brown shoes should be dark, and should work with the pants you’re wearing, which are also hopefully either brown/beige or tan, some charcoals, and dark earth toned pants (which I hope you wouldn’t be wearing much of anyway.) Bright tan shoes? Keep them for jeans or really light colored pants or leave them on the shelf, okay?

Here’s the trick though: if you’re the type of guy who thinks “can’t I just have one pair of shoes that works with everything,” then you’re missing the point. You will, hopefully, have one pair that works with 90 percent of the clothes you have and the events or occasions you have to attend. It’ll be the super-formal affairs that will make you drag out the glossy black shoes, and when those events come around, you’ll be glad you have them.

One of the best tips I’ve ever been told when it comes to men’s dress shoes: every man should have two to three pairs: one semi-formal black pair that goes with everything and can be worn for just about any occasion from weddings to work, one glossy black formal pair, and one solid brown pair for those times when black won’t do it.

Oh – and a note about the material? If you’re like most of us, you’re on a budget. You can’t go out and spend a ton of money on hand-made Corinthian leather with natural fiber stitching and whatnot. Stick with standard, durable leather and look for a brand you’ve actually heard of if you want the most longevity out of your shoes. You may also consider a shoe tree for your fancy not-often-worn shoes, but if that’s too much, just keep the box you bought them in. Keep an eye on them, keep them stuffed with the paper that came with them (or something some clean newsprint) to keep their shape, and don’t forget to polish and shine them occasionally to keep them healthy, moisten the leather, and to stave off dry-rot.

Now then, I hope that helps you pick a few pairs of shoes to keep in your closet. After all, there’s no way to tell that the next job you have will let you wear your chucks to the office every day, and when you interview for that next job, you won’t want to wear them anyway. Now go forth and dress up your feet! You can thank me later.





One response to “The Geek’s Guide to Picking the Right Shoes”

  1. kanundra Avatar

    I just picked up 3 new pairs of shoes- Running, dress, and casual. This article came a little late for me, but I’m a sucker for good fitting shoes. I guess that’s what I get for having 4E-5E wides (and that’s narrow for my family)!

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