Nothing kills an outfit like the wrong shoes. I see it all the time, guys wearing running shoes with a giant athletic logo splashed across the side with their day to day outfits. Guys, please don’t do this. Save your running shoes for the gym, there’s a much better looking and equally comfortable solution that should have your attention instead: The Dressy Sneaker. You’ve probably seen me mention “dressy” sneakers as a wardrobe must and they are! In this post, I’m going to dive a little deeper to explain exactly what is a “dressy” sneaker and how and when you should wear them.

Don’t let the word “dressy” throw you off, it’s just a way to describe a sneaker not meant for the gym or other athletic activities. Instead, dressy sneakers are great for day to day wear like hanging around town, coffee shops, brunch, bars, casual dates, picnics, running errands, day parties, casual work enviornments, travelling etc. Alright, let’s dive in to the wonderful world of dressy sneakers!

What Are Dressy Sneakers?

When the word sneaker comes to mind, it’s easy to think of your classic Nike or Adidas brightly colored running shoes. There is nothing wrong with those shoes, but I don’t want those to be your go-to shoes for casual wear. Dressy sneakers are more sleek and subtle by usually being solid in color, made of leather or suede, and have a 1 inch flat rubber sole.

Compare the footwear in the image on the left and right….

Good Example

Bad Example

Photo Credit: Pinterest, I Am Galla

The right looks so much better and way more intentional and put together. The one on the left looks amateur.

How Do You Wear Them

Whenever you want to dress casually or dress down a dressy look, your sneakers can help you achieve this without sacrificing style. Whether it’s t-shirts, henleys, button downs or jeans, chinos or shorts, your sneakers will work with all your looks. To better explain how to put your outfits together, let me breakdown a couple of looks for you.

Casual

Photo Credit: Pinterest

Outfit Breakdown: Sweatshirt, joggers, white sneaker

Note: The white sneakers make this very casual look very well put together.

Photo Credit: Primer Magazine

Outfit Breakdown: Henley, cardigan, jeans and sneakers

Note: This is such an easy and comfortable look and the rolled up jeans and sneakers pull the look together perfectly.

Photo Credit: D’Marge

Outfit Breakdown: Bomber jacket, t-shirt, shorts and sneakers.

Note: The beauty of sneakers is they can go with shorts and make a very casual outfit look very stylish and sophisticated.

Photo Credit: Pinterest

Outfit Breakdown: Casual denim shirt, white t-shirt, rolled up black jeans and white sneakers

Note: If you’re into the unbuttoned shirt look, your sneakers will work really well with it.

Smart Casual

Photo Credit: He Spoke Style

Outfit Breakdown: Leather jacket, tucked in button down, chinos and leather sneakers.

Note: If you like looking a little more dressed up, your sneakers can keep the look relaxed, but still sophisticated.

Photo Credit: Pinterest

Outfit Breakdown: Crew neck sweater, casual slacks, brown leather slip on sneakers.

Note: If you want to make the most of your slacks, you can dress them down by wearing no show socks and sneakers. If you hate laces, this is a great example of slip on sneakers instead of lace ups.

Photo Credit: I Am Galla

Outfit Breakdown: Button down, chinos, brown leather sneakers

Note: If you love a classic button down and chinos look, your sneakers can help make this look weekend friendly.

Photo Credit: Pinterest

Outfit Breakdown: Casual blazer, t-shirt, chinos and white sneakers

Note: This is the perfect example of how sneakers can make a casual blazer look very comfortable, stylish and weekend appropriate.

Photo Credit: TheCuff.co

Outfit Breakdown: Half sleeve button down, rolled up chinos, no-show socks, and white leather sneakers

Note: I love this look for summer, it’s so stylish and easy to wear. You will be sure to stick out of the crowd in a very stylish way.

Dressy

Outfit Breakdown: Casual suit, dress shirt, sneakers

Photo Credit: Lifestyle By PS

Note: If you’ve ever wanted to wear a suit casually, your dressy sneakers will help you achieve it.

Photo Credit: Lifestyle By PS

Outfit Breakdown: Casual suit, dress shirt, sneakers

Note: Curious to try a t-shirt and casual suit look? Throw on a pair of dressy sneakers and you’ll be good to go! Jay-Z (the rapper) wears this look a lot and I love it. The key is to wear a cotton or other casual fabric suit.

No Show Socks

Photo Credit: Pinterest

Wearing no show socks when you’re wearing joggers or rolling your pants with your sneakers is going to earn you 100x style points. This small detail shows you know how to rock a pair of dressy leather sneakers the right way. No-Show socks can be purchased from anywhere. The key is to have a rubber backing in your sock to prevent them from slipping. Trust me, the most annoying thing is when you need to constantly pull up your no show socks. Here’s what I found on Amazon!

How To Lace Them

Some laces end up being very long and you end up getting a giant bunny loop situation happening in your shoes, which throws off the clean and sleek look. It happened with a client of mine, he had these beautiful black dressy leather sneakers on and every time he’d try them on with an outfit, something was putting me off. I couldn’t quite figure out what it was that made them look very amateur and young. I took his shoes and hid the bunny loops behind the tongue of the shoe and he slipped them on. Boom! There it was, the amateur look was gone and a minimal sleek sneaker was shining in all its glory. He was even blown away of how big of a difference this small detail made.

Photo Credit: Pinterest, TheCuff.co

The laces on the left look terrible, the laces on the right look so sleek!

To achieve this clean look, try the “Display” shoelace method.

Photo Credit: FatSuckingMisquitoes.tumblr.com

“Display” refers to how stores set up their shoes to look nice and sleek. The key have the very top of the laces go into the lace hole rather than come out. You can tie the laces behind the tongue and make them slip on shoes. Additionally, you can get Shoelace Lock Clips, so you don’t have to constantly re-tie your shoes.

Slip-On Sneakers

If you hate the thought of laces all together, you can go for dressy slip on sneakers. You can wear them exactly the same as lace up sneakers.

Photo Credit: The Style City

Slip on sneakers look slightly more casual than sneakers with laces, however, they can achieve a very similar effect. Who doesn’t want shoes that are easy to slip in and out of?

Hybrid Sneakers

Hybrid sneakers are interesting mix of dress shoes and sneakers. They offer a stylish and unique look if you’re ready to step up from a simple sneaker. Hybrid shoes have the look of a dress shoe (i.e. oxford, derby, monk strap etc.) at the top, but the sole of a running shoe. My personal favorite is the hybrid monk strap sneaker.

Photo Credit: Cole Haan, Florsheim

The photo on the left is an Oxford Hybrid Sneaker. The photo on the right is a Monk Strap Hybrid Sneaker.

Photo Credit: DG Manila, Pinterest

The key is to wear no shoe socks and ankle pants to make this look modern and sleek. You can wear this style of sneaker with a blazer and chinos for a Smart Casual look as well.

Colors

My top recommendtions for dressy sneaker colors are: white, black, grey or brown. These neutral colors will go with almost all of your outfits. Let’s look at the colors in more detail!

White

Photo Credit: Common Projects

White is pretty classic when it comes to dressy sneakers. You will notice the majority of my photos had white sneakers because those are the ones that look the freshest. However, they do require a bit more maintence because you want to keep them white and clean. If you’re up for the challenge, I personally say white sneakers look the most stylish.

Black

Photo Credit: Greats

If white makes you feel overwhelmed, go for black sneakers instead. They’ll go with everything and be easier to maintain.

Brown or Burgundy

Photo Credit: Magnanni

Grey

I personally love brown sneakers, especially when they have a “wood” finish like the example above. They are great for breaking up dark outfits and are more rare than black and white.

Photo Credit: To Boot New York

If you want something softer than black, but not as bright as white, try grey! Grey shoes are very neutral and will go with a lot of colors. Grey suede is a favorite of mine because it has a softer effect and looks very classy. However, you never want to wear suede out in the rain because it will get ruined. Alternately, grey leather is a great option if maintaining suede scares you.

Care

Photo Credit: Amazon

Get a protect all spray (left) and an odor spray (right) .

The more you take care of your shoes, the longer they will last. Clean your shoes every couple of months (or when they start looking a bit worn) and spray them with a water-repellent protector. Protectors are great because if you spill anything like red wine on your white shoes, the drops will slip right off. I like the Jason Markk spray because it doesn’t yellow your shoes like some sprays can.

Dirty laces are a style killer, so make sure your laces look fresh. You can wash your laces if they start to look dirty. However, if they are really looking worn, replace them.

If you have a tendency to ruin your shoes because of odor, keep a odor fighting spray around and spray them after a couple of wears or more often if you need to. I personally like this Spray. It’s normal for shoes to smell eventually, especially if you are wearing thin socks. Don’t ever not wear socks for the no-show sock look, you will ruin your shoes much faster.

When Are Dressy Sneakers Appropriate?

Just because they are considered a “dressy” sneaker, doesn’t mean you should be wearing them at formal events or parties. Save your leather sneakers for your casual and smart-casual outfits. If your workplace is casual, you can wear them there.

The casual suit look with sneakers is best for weekend or vacation, when you want to look sleek and relaxed. Day time parties are great for this look as well!

When Are Actual Running Shoes Okay?

For the most part, save them for the gym or athletic activities. However, if your outfit is very casual like joggers or sweatshirts, you can wear your running shoes out and about. When you are wearing jeans or chinos, don’t wear your running shoes. I know sneakerheads won’t agree with me on this, but we’re aiming for smart and classic styles, not trends.

My Top Sneaker Picks

Dressy leather sneakers can range anywhere from $50 to $500, depending on what you are looking for and your budget. The most important thing to look for is comfort since you’ll be wearing these instead of your running shoes. Try a couple of different brands on to see what fits your foot the best. There are new brands popping up everyday specializing in dressy sneakers, so it’s best to order a couple of pairs and see what fits the best. Here are a couple of my top recommendations going from the lowest to highest pricetag:

Adidas Stan Smith or Neo ($45+)

Photo Credit: Adidas

Adidas is a classic brand that comes to mind when it comes to sneakers. They have their Neo white on white sneaker that is super clean and at a low price point. The Stan Smith is their more popular one, which will run you about $75.

Cole Haan Crosscourt ($70+)

Photo Credit: Cole Haan

Cole Haan makes really lightweight classic dressy sneakers at a good price point. You can typically find them for $70 to $100, depending on if you can get them on sale. Cole Haan also plays around with hybrid sneakers a lot.

Ecco Soft 8 ($150+)

Photo Credit: Ecco

Eccos are one of the most comfortable shoes you will probably try on. I especially like their Danish collaboration for very minimal and sleek sneakers. Eccos will run you about $150, but you can sometimes find them on sale.

Greats Royale ($180)

Photo Credit: Greats

Greats is a Brooklyn based brand that has been around for a couple of years and produce excellent quality Italian sneakers. They have a weatherproof version too! Greats will run you about $180 for the classic leather sneaker, but you will get free shipping, free returns and great customer service. If you sign up for their email list, you can get 10% off.

To Boot Knoxx ($325)

Photo Credit: To Boot

If you’re ready to invest in your sneakers and absolutely love quality and crafttmanship, To Boot makes an excellent dressy sneaker. If you love the suede look, they have a couple colors out every season. They will run you about $325. Keep a look out for them on sale.

Magnanni Elonso ($325)

Photo Credit: Magnanni

Common Projects ($400)

If you’re ready to splurge, Magnanni is an Italian brand that nails the dressy leather sneaker as well. I love their wood finish sneaker I showed in the brown category as well as the clean look they offer. You can sometimes find them on sale, so keep a look out. These will run you about $325.

Photo Credit: Common Project

If you’re looking for the trendiest brand and quality dressy sneakers, Common Projects could be for you. They are handmade Italian sneakers that became very popular in the last couple of years. Be prepared to spend a shiny penny, but they do look pretty sleek and have a cool logo. Common Projects will run you about $400.

There you have it, one of the easiest and most comfy swaps you can make in your wardrobe to look modern and stylish. Hope you enjoyed the post! Feel free to reach out if you have any questions or want me to tackle other burning questions you may have.

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Supreet Chahal

Supreet is a Fashion Stylist from San Francisco, CA. She helps both men and women establish a sense of style and dress with confidence. If you want to work 1:1 with Supreet, visit StyleBySupreet.com. If you're a guy looking to learn more about style, check out PocketStylist.io, a site dedicated to teaching men how to dress well.

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