The Tomboy’s Guide to What to Wear with Gray Shoes

So you’ve got your eye on a snazzy pair of gray shoes, but you’re not really sure what kind of outfits you would wear with them. Not to worry! There are a surprising number of ensembles that work with gray or silver shoes, and lots of situations where it’s appropriate to whip them out.

What Time of Year to Wear Gray Shoes

Fall is the ideal time of year to wear your gray shoes. They’re perfect for lightening up a wardrobe that can otherwise be dark and heavy, especially if you switch to denim pants in the fall. Some high quality gray oxfords are unusual enough of a color that they communicate both playfulness and sophistication, so they can work with both formal and casual outfits. Worn out with a pair of dark jeans and a cozy sweater in a classic autumn color, your shoes will declare that you know it’s getting colder but you’re not ready to give up being cheerful with your fashion choices just yet!
The neutrals of fall work relatively well with gray, but the sharpness of some grey shoes in winter really lends itself to use in the coldest months as well, if you’re wearing them indoors or have a pair that are relatively weather resistant. If you’re going to wear vegan leather or genuine leather dress shoes outdoors in the winter, take care to keep them dry and maintained with shoe polish when they’re not being worn.

What Colors to Wear with Gray Shoes

When you’re picking out outfits to go with gray shoes, you want cooler tones. Blues, greens, purples, and of course black and white and gray. Pairing gray shoes with a mostly black or dark blue outfit gives it a little pop of lightness and personality. If you wear a lot of black, the gray shoes offer a non-black option that matches the aesthetic but gives you some variety to work with.
You may actually want to steer clear of matching gray bottoms to these shoes – the match has to be absolutely perfect for it to look deliberate, and if it doesn’t look deliberate it just sort of looks like a clumsy wardrobe choice that resulted in a misbalance in your outfit.
Gray shoes are an excellent choice if you want to rock some patterns; the shoes act as a balance that is both neutralizing and cheerfully encouraging. As long as you don’t overdo it – you only really need one pattern with this kind of outfit, not three patterns and a dozen statement piece accessories – you can achieve a wonderful and visually pleasing balance between your top and bottom.
Remember that you can mix your neutrals! If you’ve got a solid capsule wardrobe your foundation pieces should consist of a lot of neutral tones that you can safely wear out and about with your gray shoes without having to stress too much about it.

What Belt to Wear with Gray Shoes

There’s a whole system for knowing what belt you’re supposed to wear with what shade of shoe, and it can be a bit overwhelming. The easiest way out is to wear a matching gray belt, but that can mean having to balance the rest of your outfit to look appropriate with both the gray shoes and the gray belt.
Although typically it’s a no-no, most people won’t scrutinize too hard if you choose to wear a dark brown belt with gray shoes, and you’re always safe if you just go with a simple black belt with a silver buckle. Grey shoes are the perfect item to pair with a belt with a pattern, like a black tooled leather belt with white accents.
If it fits with the rest of your outfit, this is actually a rare pair of shoes that can be paired with a white belt for a clever and flashy combination. The main thing you want to avoid wearing is a light brown belt, which is just close enough in tone to be in competition but just different enough to clash.


What Formal Clothing to Wear with Gray Shoes

If you’re a person who wears suits or dress shoes to the office every day, we’d advise that gray shoes are an excellent addition to a wardrobe, but maybe not the ideal starting point. If you wear black men’s dress shoes every day, nobody is going to notice; the same cannot be said for gray shoes. If you already have a nice pair of black shoes and a nice pair of brown shoes, however, gray shoes are an excellent next step for bringing a little variety and aplomb to your presence in the board room.
You can wear light gray dress shoes with a navy suit or a black suit, or a very dark charcoal suit. These rules also apply for weddings, where you can up your dapper quotient by adding a matching gray vest to your ensemble to really balance out the lightness of the shoes with the heaviness of the suit and pants. Alternately, you could go for a vest that matches your jacket and elect to wear a light gray tie on a white dress shirt.
If you’re stuck for wedding wear ideas, just remember that you can’t go wrong with a black pants and jacket with a white dress shirt, and a pair of gray shoes absolutely fits the bill for that combination. You might bring up the fun levels of such a suit with a gray bowtie to play off the shoes and a vest in a color like blue, purple, or burgundy.


What Accessories to Wear with Gray Shoes

Gray shoes are particularly forgiving when it comes to accessories. Unlike blue shoes, which count as a statement piece in their own right and require your fashion arithmetic account for them when you’re keeping yourself from committing the fashion sin of wearing too many statement pieces at once, gray shoes are neutral enough that you still have room to add more flair on top of them.
You’re freed from the obligation of staying matchy-matchy with these shoes – you could wear a little bit of silver or gray in your watch strap or in a necktie or piece of jewelry, but you actually will look better with a little color instead of sticking to pure gray. This is especially true of outfits that are comfortably neutral or uses dark, cool tones – you can confidently rock your favourite accessory as long as it matches the rest of your ensemble.

1 comment

  • Justin

    this was so helpful thank you

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