Best Ways To Wear Jeans With Sneakers/Trainers, Boots, Dress Shoes For Men

There’s many different types of shoes and jeans/denim you can wear but depending on the shoes, your jeans need to be certain colors and fit certain ways in order to look their best, so today we’re going to show you the best ways to wear jeans with High and Low top Sneakers/Trainers, Boots, Chukka Boots, Chelsea Boots, Work Boots, Dress Shoes, Brogues, Monk Straps, Loafers, Penny Loafer and more. 

 

Low-Top Sneakers

Due to the low profile of lowtop sneakers its really hard to mess this up. They’ll work with almost any cut of jeans.

As for denim colors or styles, unless they’re all black sneakers (which we discussed before), you can pretty much wear any color or style you want. The one caveat is that if you’re wearing white sneakers and dark indigo jeans, they can stain the tops of the shoes. So soak the pants in cold water for about 30 minutes to get rid of any excess dye that may rub off on the shoes and then spot clean the shoes, as necessary.

If you want to avoid staining the shoes all together, either get them hemmed or cuff them to not touch the tops of the sneakers. We’ve done a whole article and video about cuffing your jeans here.

Hi-Top Sneakers

If you’re going to buy hi-top shoes and wear them with the hem going past the tops of the shoes, you should just get a lowtop pair of sneakers instead. We’ll assume you are wearing hi tops because you like the look of them and want to show off the whole shoe.

To do this well, either gets your pants hemmed shorter or cut them with scissors for a frayed look to show off the shoes or simply roll them to just below the top of the hi tops. Never more than twice, though, otherwise you’ll have a really thick cuff on the bottom and it will look very heavy and off on your shoes.

Running Shoes/Trainers

There’s two schools of thought here and it depends on how “chunky” the running shoes are. If they’re low-profile and sleek, then stick to a similar cut as low-top sneakers – which means wear any cut of jeans. You can even cuff your pants if you want a sportier look.

If you’re going for the Dad/Ugly sneaker look, then the chunkiness of them dictates you go for a straight leg, more relaxed cut. The more stonewashed, the better!

Dress Boots

These will pair really well with dark-wash or black jeans. Just make sure you’re jeans have a slight to no break to match the sleeker and more polished dress boots. Wearing dress boots and stacked hems is like wearing tuxedo shoes with jogger pants – it just doesn’t look good.

Work Boots

These boots tend to have a chunkier sole and more casual appearance, so definitely play up the workwear version and wear them with dark wash denim or denim that has some fading. And cuffed or uncuffed, you can wear them anyway you want. If you’re going for the super slim fit jean and chunky boot look (Justin Theroux), get them hemmed or roll them up to be shorter and leave no break. If you want a super vintage look, then try a single, oversized cuff and a more relaxed fit.

Desert & Chukka Boots

Wear them with any color and cut of jeans you prefer and they tend to look best with a slight or no break, depending on the look you’re going for. You can achieve this by cuffing your jeans or getting them hemmed.

Chelsea Boots

As we talked about in a separate video, Chelsea Boots are not for everyone- if you’re a bigger guy, stick to work boots unless you want to look like Humpty Dumpty with little tiny legs. Chelseas need to be paired with slim jeans to look their best. The color and material of the boots will determine what you should pair them with.

If you’re wearing black leather or suede chelseas, they’ll look best paired with black or gray skinny jeans. Anything outside of this will be much harder to pull off.

For brown or tan suede Chelseas, especially with a gum sole, go with a lighter blue or gray denim, which can also have some distressing.

If you’re going with brown (not tan) leather Chelseas, a dark wash denim will look best since browns and dark denim are a match made in heaven.

Debries & Brogues, Oxfords, Wingtips, Monkstraps (Dress Shoes)

Derbies, like Doc Martins, feature a chunkier profile, so they’re better suited for casual outfits that include denim. Black looks great with black or dark wash denim, while brown looks great with dark washed, stonewashed or even distressed lighter denim. If you want those late 80’s or early 90’s vibes, pinroll your jeans and wear them with white socks (I know we’ve talked about our hate of white socks before, and that still holds true 99.9% of the time. This is literally the .1% of times it will look good due to the specific, era-related look you’re going for.

For Brogues, as a general rule, the sleek, minimally detailed brogues will skew more formal while chunky, hole-punched ones will skew more casual. The color of the shoes affects which jeans your brogues will or won’t work with, going from black at the formal end and getting gradually lighter towards the casual end will work best. Casual tan brogues pair well with indigo or lighter denim while other colors like oxblood and black will look good with black denim. As for cut, they’ll work for any cut of denim you wear, regardless of the length of jeans you wear.

You can pull off Oxfords with black or indigo jeans, as long as they’re slim, and either cuffed or hemmed with no break so they’ll feel a little more casual, but still sleek and polished.

Loafers & Penny Loafers

The penny loafers’ low vamp (that’s the section of upper that covers the front of the foot) combined with a wide leg opening can make your feet look weirdly stubby. So opt for jeans that are tapered and cropped or pin-rolled. As for colors, we love a medium brown pair that goes well with dark wash indigo but can also be paired with any lighter colors up to white denim. Black penny loafers will look great with gray or indigo denim.

Sneakers Every Man Should Own

I talk a lot about what a crucial part of your wardrobe sneakers are and they definitely shouldn’t be an afterthought.  There are many great ones out there, but not all sneakers are created equal. Having a selection of classic, versatile styles will definitely take your casual wardrobe to the next level.  With that, here are my picks for the sneakers that every man should own!

 

Canvas Sneakers

PF Flyers 

These were also my top pick this year for shoes you need to own in 2018, and for good reason, they’re cheap, breathable, comfortable and have a unique take on the classic canvas sneaker.

Vans Classic or Converse All Star

If the PF Flyers aren’t up your alley or you want something other than white, consider one of these super classic, never-go-wrong sneakers. They’re cheap and look awesome with pretty much everything. I love them in white, navy, gray or even black.

Leather Sneakers

Stan Smith or Common Projects Achilles

I’ve talked about white leather sneakers a ton; I love how they’re clean, classic and add a little extra polish to a casual outfit. If you’re not a fan of white, definitely get the gray or blue versions of these.

Running Shoes

New Balance Retro Sneaker

Like I mentioned in my top shoe video, these New Balance retro running sneaker are affordable, look great, and are very comfortable. I love the woven upper, as it makes them extra breathable and very comfortable-just like wearing socks.

Adidas P.O.D. S3.1 or Ultra Boosts

Ultra boost soles are like walking on marshmallows, they’re the most comfortable sneakers I’ve ever worn. Plus these are cool and unique without being crazy loud like other running shoes can be. If you want something less flashy, the classic Ultra Boosts are the way to go.

High Top Sneakers

Converse All-Stars

I like the all-white over all-black because the all black is really heavy-looking on your feet. If you want black, I’d actually suggest getting a version by John Varvatos, they’re a well-designed take on the classic Converse-style high top.

Nike SF Air Force 1

For those of you who really like a sporty high top sneaker, here’s one of my favorites that I’ve styled on a couple of my clients. I like the black and white colorway of these but the all-white ones look great too. I love the clean silhouette and the dual zippers at the heel make these shoes super easy to get on and off.

So those are my top picks for sneakers every man should own, hopefully you’ve got a few of them lined up in your closet!

Should I keep this new M65 jacket?

He wanted to know whether he should keep the jacket or not. I say HELL YES! The fit is perfect, and it breaks up the black color pallet he’s wearing, as well. I really like the small band of gray shirt at his waistline. He did a great job of breaking up a huge swath of black under the jacket.

I’m not the biggest fan of his printed t-shirt, but I’m not a fan of logos or artwork on clothing in general, so it’s just my preference.

Click here to see more of the thread.