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.

5 Men’s Shoe Styles Women Love

By now you know how important a strong shoe rotation is to your overall wardrobe. As we talked about in our previous video, Shoes Women Hate, your footwear is a big part of what women notice about your right off the bat. Outside of choosing the right style, it’s important to keep in mind that you also need to wear the right shoe for the right occasion, too formal or too casual a shoe with the wrong outfit can throw off your entire look.

In this video, we’re going to flip the coin and run down the key styles that women will really notice. From sneakers to dress shoes, here are 5 shoe styles women love.

5 Shoe Styles Women Love

1. Casual Leather Sneakers – Classic and versatile, they go with almost every casual outfit. Just make sure to keep them clean! White, Gray, Tan, Black.

Penny Loafers – Another classic, they elevate every casual outfit with a little bit of polish. Wear them with denim, chinos, and even dressier business casual outfits.
Chelsea Boots – These boots are super sleek and sexy, a perfect fashion-forward item to give your wardrobe a little bit of edge. Leather or suede works.
Classic Lace Up Dress Shoes – When you’re dressed to the nines the wrong shoe can absolutely ruin how awesome your suit looks. Stick to a clean, classic oxford in dark brown, it looks powerful and professional. Don’t forget to keep them shined.
Lace Up Boots – A nice boot looks amazing with denim or chinos and is a great way to add a bit of ruggedness to your wardrobe.

POTW: Johnston & Murphy Burgundy Cap Toes

I was prepping for a fitting, and I came across these Johnston & Murphy burgundy cap toes that I thought you should know about. I’m not normally a fan of burgundy shoes because I often find the color to be difficult to wear and usually ends up being too much of a statement piece. But, these are different because the darker color is closer to a burgundy brown instead of the more reddish-oxblood color you often see with other “burgundy shoes” and that makes them much easier to wear. So, I had to make them my pick of the week!

$155 – Johnston & Murphy Burgundy Conard Cap Toe

Best Ways to Wear

The decorative broguing along with the brown soles adds a casual look to them making them easy to wear with your summer suits, like a green or navy cotton suit, or with some chinos or dark wash jeans. Blues, greens, and khaki go great with burgundy. If you’re ever unsure how to wear these, just know that whenever you wear brown dress shoes with a more casual outfit, you can easily wear these instead.

I also want to address the contrasting stitching. On more formal shoes it can be very distracting and pull the attention away from your outfit and really focus it on the shoes. But on a casual dress shoe, such as these, it works because you’re never going to be wearing them with a really formal outfit. So if you’re thinking about doing that, then please don’t.

Like I’ve said before, accessories are a great way to add some fun touches to your outfit and these shoes do exactly that.

Look 1

$40 – J. Crew Slub Cotton Deck-Striped T-Shirt
$68 – J. Crew Navy or Green Stretch Chino Pant in 770 Fit
$30 – Uniqlo Slim Fit Flat Front Chino in Navy

Look 2

$69 – Brooks Brothers Selvedge Oxford Sport Shirt
$70 – Levi’s 511 Slim Fit Stretch Jeans (in blue flame, dark hollow and stump town)
$228 – JBrand Tyler Fit in Blue Hood

Look 3

$358 – J. Crew Ludlow Suit Jacket in Italian Cotton Oxford
$188 – J. Crew Ludlow Suit Pant in Italian Cotton Oxford
Shirting – See my dress shirt article
Ties – See my ties article

21 Things Men Should Never Wear

In this video, I talk about the 21 things men should never wear! These are the things that’ll curl your toenails, and offend even your grandmother. Just don.do.it.

1. Gaudy Rings & Pinky Rings

2. Too Much Cologne

3. Socks with Sandals

4. Sandals In General

5. Shorts That Go Past Your Knees

6. Old dirty shoes

7. Cartoon printed boxers

8. T-Shirts with Brand Logos

9. Baggy, Ill-Fitting Clothing

10. Tank Tops

11. Skinny Jeans

12. Pointy & Square-Toed Shoes

13. Deep V-Neck T-Shirts

14. Big, Square, or Monogrammed Belt Buckles

15. Leather Bracelets

16. Elongated Shirts

17. Soul Patch

18. Crocs

19. Earrings and Facial Rings

20. Short-Sleeve Sweaters

21. Dress Shoes with Tennis Shoe Soles

The #AskAW Show Episode 11

Articles/Stories Referenced In Video

Weekender Bags

How To Match and Wear Colors

Suits & Sport Coats/Blazers

Oxford Dress Shoes and Monk straps, Wingtips, Brogues

Men’s Dress Shoes – Monk Straps, Brogues, Wingtips

Let’s talk about my favorite and what I consider the best men’s dress shoes for Fall and Winter – Monk straps, Brogues, and Wingtips.

Quick note: Wingtips are technically Brogues, so I’ll be lumping them together throughout this article. Just know when I refer to Brogues that I also mean Wingtips.

I prefer these during the cooler parts of the year because they go much better with the heavier wool and cotton items you wear in your Fall and Winter outfits. Don’t get me wrong, they also work year-round, but I think there’s better options out there for the other parts of the year. Check out my Summer Essentials Ebook and Wardrobe Essentials Series for details about those options.

Below are the things I look for in a good pair of Monk Straps or Brogues.

MATERIAL

As I said in my Fall/Winter boots story, I love a good calf skin. Don’t get me wrong, I love a suede monk strap or brogue, as well, but if you live in an area with snow or rain, you’ll regret the day you wear them outside. So let’s wait to get into those until Spring or Summer.

SHAPE

I will say this about dress shoes until the day I die, but you want a nice, slim profile with a rounded toe box. Ain’t nobody got time for square or large, bulky toe boxes! – See the video near the top of the article if you’re unsure about what they look like.

COLOR

As for colors, I love a nice dark chocolaty brown, or even a medium brown, like a walnut. Black is also good, but the first color I’d get is brown because it goes better with all the Fall colors in your wardrobe. All these colors are represented in my suggestions at the bottom of this article.

SOLES

If you live somewhere with a bit of rain, ice or snow, then you can and should definitely have these with Dainite or rubber inset soles for added traction. If you don’t live in that kind of climate, then a regular leather bottom that you’ll find on 99% of dress shoes is perfectly acceptable, but I’d probably look for a Dainite or rubber insert sole as my default. There’s also lugged soles, which are pretty popular right now (and I included some in my selects below), but I have a feeling they won’t be around for the long haul. They’ve already come and gone with fashion a few times in my lifetime. When it comes to Fall/Winter boots, though, I love me a lugged sole.

MONK STRAP SPECIFICS

I prefer a double buckle because a single buckle looks less refined. (Example in the video at the top).

If you get black Monk Straps, make sure the buckle is silver, because gold or brass tends to look gaudy, but is perfectly fine on brown monks (examples in the video).

Also, please make sure the buckles are on the smaller side as opposed to some big ass buckles you’ll find on a colonial gentleman.

As for medallion toes and other flourishes, I like all of them, so check out my recommendations below.

Best Ways To Wear Dress Shoes

H&M Blazer Slim Fit
Burberry White Slim-Fit Poplin Dress Shirt
The Tie Bar Navy “Score Check” Tie
The Tie Bar Olive Green 1″ Tie Bar
The Tie Bar Grey Southeast Plaid Wool Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt
Allen Edmonds Black Strand Dress Shoes
Tom Ford Snowdon Sunglasses
IWC Portugieser Automatic Watch

Topman Light Brown Wool Rich Formal Coat
Burberry Slim Fit Cotton Poplin Dress Shirt
The Tie Bar Webster Medallions Tie
J.Crew Slim Merino Wool Cardigan
John Varvatos Grand Sunglasses
J.Crew Ludlow Suit Pant in English Donegal Tweed
Johnston & Murphy Nolen Double Monkstrap Shoes

Brogues & Wingtips

Budget Friendly

Vince Camuto Tallden Black Wingtip Oxford

Vince Camuto Tallden Brown Wingtip Oxford

$130 – Aldo Bartolello
$165 – Johnston & Murphy Jennings Wingtip
$195 – Vince Camuto Tallden – Wingtip Oxford (2 colors)
$225 – Vince Camuto Benli Oxford

Designer

$395 – Allen Edmonds Strand Cap-Toe Brown Oxfords with Dainite Rubber Sole

These, to me, are the quintessential Brogue. If you’ve seen my other dress shoe article then you know my love of Allen Edmonds. They make amazing products with great value – and they don’t pay me to say that. I’m just a huge fan.

I love this color and the Dainite soles. They’re just perfection.

allend-edmonds-mcallister-wingtips-ashley-weston

churchs-toronto-cap-toe-leather-oxford-ashley-weston

George Cleverley Henry Pebble Grain Wingtip

George Cleverley Henry Pebble Grain Brown

$395 – Allen Edmonds McAllister Wingtip with Dainite Rubber Sole
$395 – Allen Edmonds Strand Cap-Toe Black Oxfords with Dainite Rubber Sole
$650 – Church’s Toronto Cap-Toe Oxford Brogues
$780 – Prada Runway Hybrid Wing-Tip Oxford
$1,990 – Tom Ford Austin Cap Toe Oxford Shoe

Monk Straps

Budget Friendly

$185 – Johnston & Murphy Nolen Double Monk Cap Toe

These hit all the points I look for in a double monk – the beautiful chocolaty brown with the matching soles, the silver hardware and the rubber tread inset for added traction. On top of that, they’re a GREAT price and my clients always comment about how comfortable they are. My other favorites are the Allen Edmonds Monks below, if you’re looking for something higher quality.

Kenneth Cole Regal Bearing Black Monk Strap

Kenneth Cole Regal Bearing Brown Monk Strap

Vince Camuto Briant Black Double Monk Strap

$99 – Kenneth Cole Regal Bearing Leather Monk Strap Dress Shoe (2 colors)
$160 – Aldo Caresien
$225 – Vince Camuto Briant Double Monk Strap Shoe (2 colors)

Designer

$395 – Allen Edmonds St. Johns Black Double Monk Strap

Allen Edmonds St Johns Brown Double Monk Strap

Crockett & Jones Lowndes Black Monk Strap

Crockett & Jones Lowndes Brown Monkstrap

Crockett & Jones Harrogate Double Monk Strap

$395 – Allen Edmonds St. Johns Brown Double Monk Strap
$395 – Allen Edmonds Mora 2.0 (3 colors)
$435 – Crockett & Jones Lowndes (2 colors)
$700 – Brooks Brothers Peal & Co. Double Monk Strap

Men’s Summer Essentials Ebook

In this ebook, I’ll detail the items you need for summer, why you need them, and where to get them – in designer and budget-friendly options.

These items will work very well with the rest of your year-round essentials, so if you haven’t seen that series, check it out first.

My goal is to ensure you’re comfortable, wearing appropriate colors and items for the season, while looking amazing and not like a douchebag.

So fill out the form below, download the book, pour a glass of… something (I prefer rosé) and let me show you the good stuff!

James Bond Casual Style

This article & video is part of the Celebrity Style Inspiration Series, where Antonio Centeno from RealMenRealStyle.com and I pick out great outfits from movies and tv shows and demonstrate how to recreate and incorporate them into your wardrobe.

As Antonio and I discussed in our other video about James Bond outfits to emulate, I really love the casual outfits Daniel Craig wears, so I wanted to recreate this one from Quantum of Solace, because it’s clean, simple and looks amazing on every guy, regardless of his age or body type.

Unlike the other video, where I switched out some items for more practical options, this one is already very practical, aside from the shoes. But we’ll get into that in a moment.

Here’s the full outfit I’m going to recreate. Apologies for the blurriness, but they don’t show this outfit for very long and the full-length shot is focused on a woman in a bikini to the right of Bond.

The Cardigan & Shirt

Daniel Craig is wearing a black shawl collar cardigan which is so warm and comfy. I certainly wouldn’t advise wearing this during summer time, but for any other time of year, there’s nothing better than a shawl collar cardigan. I put my model in one from Todd Snyder, but check the outfit details at the bottom of this page, because Todd Snyder no longer makes that cardigan, but I included a very worthy substitute.

Now, with the shirt, you can either go with an Oxford button down, like I have my model wearing below or you can go with a semi-spread collar dress shirt. if you wanted to dress it down a bit more, you can go with a white v-neck t-shirt, like Daniel Craig also wore in Casino Royale.

Pants, Shoes & Sunglasses

As for the pants, tan or sand colored chinos are perfect here. Just please make sure that they fit properly, otherwise it won’t look so great.

In the full length image at the top of the page, you’ll see bond is wearing brown suede chukka boots, which as I mentioned in the companion video to this one on Antonio’s Real Men Real Style channel, I’m not the biggest fan because they get gross and dirty quite quickly. So instead, I’d go for something like brown oxford dress shoes. That way, you’ll keep the same general profile as the original outfit and you hopefully already have these in your closet, so it’s a perfect way to incorporate them into a more casual outfit. I find a lot of men have a problem with mixing their dress shoes into more casual outfits and this is a perfect example of when it’s appropriate to add them in.

The final piece of the puzzle is the sunglasses. Daniel Craig is wearing aviators by Tom Ford in the film, but whether you should be wearing those or another style is dependent on your face shape. Since my model has a more oval face shape, I went with squared Tom Ford wayfarer-style sunglasses instead.

My Version of this outfit

I also wanted to mix a more budget-friendly piece, like the chino pants, with less budget-friendly items, because for some reason, a lot of men think that if they’re wearing an expensive item, everything else has to be equally expensive or it just won’t look right. Well, hopefully you see that this couldn’t be further from the truth.