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.

Top 3 Men’s Shoes For Summer

Warm weather and summer events make for special shoe demands, so you want to be prepared with the right summer footwear. You want shoes that are going to keep you cool and also look stylish with your summer looks. One caveat before we jump in though: while you may be tempted to wear flip flops all summer, don’t do it! Unless you’re headed to the pool or beach you should be wearing a proper shoe, so keep them in the closet unless there’s water present.

Don’t forget to check out all of our picks below!

 

 

 

Boat Shoes

A summer classic, these are great all around casual shoes. Stick with the classic style in leather and look for colors like brown, tan, navy, or grey. Despite what you may have seen, these aren’t meant to be dressed up though, only wear these with shorts and very casual chino outfits.

Boat Shoe Picks:

Sperry

L.L. Bean

Rancourt & Co.

 

Espadrilles

A stylish warm weather canvas shoe, espadrilles are very lightweight and breathable. These look great with everything from shorts to chinos and you can get them in solid colors or go for a fun pattern.

Espadrille Picks:

Soludos

Diegos

Castaner

 

Suede Driving Mocs

A great casual shoe with a little more polish, you can wear driving mocs with everything from shorts to chinos and a blazer. I recommend these in suede over leather because in the warmer months leather can just look a bit to heavy and formal. Two rules about drivers I always see guys break: never wear them with a suit (too casual), and always wear them without socks or with no-show socks.

Suede Driving Moc Picks:

Tod’s 1

Tod’s 2

M. Gemi

Budget-Friendly

Dorian’s Outfit

Floral Shirt

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.

  1. 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.

  2. 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.

  3. 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.

  4. 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.

5 Men’s Shoe Styles Women Hate

It’s a fact that one of the first things a woman notices about you is your shoes.  So obviously it’s important to make sure your shoe game is on point. We always talk about how important it is to regularly clear out old and out of style items, and shoes are no different.  Shoes are a key part of your overall look, and a few wrong choices or out of date items can easily ruin an otherwise great look. 

Here are Ashley’s picks for 5 Men’s Shoe Styles That Women Hate!

5 Shoe Styles Women Hate

  1. Square toed dress shoes
    Out of date and out of style, get rid of them right now. Get yourself a proper pair of dress shoes instead.

4. White loafers or loafers with contrasting stitching
Your loafers should always have same-color stitching and white loafers are another out of date style nobody should wear. Try our Loafer Guide for better options.

3. Chunky basketball/gym sneakers
The gym or basketball court is fine but outside of that, these shouldn’t be worn with casual clothing. White sneakers or dress sneakers are a much better look.

2. Rubber flip flops
Unless you’re at the beach or pool these aren’t a good look.

1.Slides
Keep them to the bathroom or inside the house, nobody should see these!

3 Loafers Every Man Should Own

When you’re talking about versatile, stylish footwear, there are few styles I like better than loafers. I love that they can be dressed up or dressed down, and work for pretty much every season. There are many varieties out there these days, from simple to complicated, but I’d like to focus on three primary types that deserve a place in your closet, plus a few that maybe don’t.  Get ready, it’s loafer season for a reason.

 

Penny Loafers

A classic style that has stood the test of time, penny loafers are perhaps my favorite out of all the loafers. I love how versatile penny loafers are, they can be dressed up with a suit or dressed down with everything from jeans and a buttondown to chinos and a polo shirt. Brown and black are the two ideal colors here. For a secondary choice, a classic burgundy or oxblood color is an excellent option.

My Picks

Designer:

Prada

Ferragamo

Budget -Friendly:

Johnston & Murphy

Bass Weejun

Driving Moccasins

Originally designed for, you guessed it, driving, I love this style because they’re super comfortable and work well in a variety of casual situations.  They come in a few variations but I prefer the versions with a nubbed rubber sole or a full rubber sole for the look and comfort. For colors, the basics like brown and tan are great of course, but I also recommend versions in grey or navy for a pop of color.

My Picks

Designer:

Tods

Budget-Friendly:

Zappos

Boat Shoes

Another shoe that evolved from function – the no-slip rubber sole and lightweight design worked well on boats – boat shoes have become a classic warm-weather staple. I like them best with chinos and shorts for a relaxed alternative to sneakers. On the color front, go with blue, brown and grey for maximum wearability.

My Picks

Sperry Top-Sider

Alternative Loafer Styles

There are a few other loafer styles out there but I don’t generally recommend them because they can lean too specific in their look and style.

Tassel Loafers

This dandy look is popular with a lot of style bloggers out there, and while I don’t hate them, I just don’t think they’re ideal for most men from a style standpoint. Just like your clothes, your shoes should be streamlined, and while the tassels can give them somewhat of a “distinguished” look, I find them to be distracting, like an untucked pair of shoelaces.

Horsebit Loafers

Another type with a dandyish vibe that has become popular again (you may know them as Gucci’s iconic loafer), I am not a fan of them at all. They immediately age you up (and not in a good way), and I always expect a lawyer or Wall Street guy who is trying way, way too hard to wear these.

Venetian Loafers or Smoking Loafers

Both of these have a similar, streamlined shape and a formal look. Venetian loafers are unadorned and usually in leather while smoking loafers are typically velvet and have embroidery or embellishments on top of the shoe. I always view these as super formal, and that’s why I really only recommend wearing the patent leather or velvet versions with a tuxedo if you want to add some flair. I don’t recommend more casual versions in regular leather because it’s a style that’s quite outdated and doesn’t have the versatility I like. 

My Picks

Christian Louboutin

Vince Camuto

So no matter what you’re wearing, casual or formal, get out there and wear some loafers this season, your feet (and style) will thank you.

Top 3 Outfits For Spring & Summer

The warm weather will be here before you know it so it’s time to start thinking about your Spring and Summer wardrobe options. With that in mind, here are my Top 3 Favorite Outfits for Spring & Summer 2018. All of these looks are super versatile and are going to have you looking stylish no matter what’s on your calendar. Don’t forget to check out all the info below for each outfit’s details.

 

 

Outfit #1

For this first outfit, I started with a lightweight blue suit that’s great for summer and paired it with a fun Hawaiian print shirt to add some extra personality. You could also try a floral or botanical print shirt, and it’s a great way to give your suit a whole new vibe. I then added a tipped pocket square that picks up some of the colors in the shirt and finished the look with penny loafers and a cool pair of blue framed sunglasses. For a relaxed suiting look like this, I also like having a slightly shorter hem on the pants to show a bit of ankle.

Outfit Details

Designer Suit: Brooks Brothers Suit

Budget-Friendly Suit: H&M Linen Suit Jacket and Linen Suit Pants

Floral Shirt: J. Crew Shirt 

Shirt Alternative: Topman Shirt

Pocket Square: The Tie Bar Pocket Square 

Designer Loafers: Prada Loafers

Budget-Friendly Loafers: Johnston & Murphy Loafers

Sunglasses: Warby Parker Sunglasses 

 

Outfit #2

For the second look, I went with an everyday monochromatic look that’s relaxed but still well put-together. This light blue shirt in linen very lightweight and breathable and I paired it with another summer staple, a crisp pair of chinos. I finished the look with grey suede driving loafers to bring it all together.

Outfit Details

Shirt: Uniqlo Linen Shirt

Chinos: J.Crew Chinos

Alternative: Uniqlo Chinos

Belt: Brooks Brothers Leather Belt

Shoes: Tod’s Suede Tie Driving Moc Loafers 

Loafer Alternative in Brown: Tod’s Suede Driving Moc Loafers

Budget-Friendly Loafer Options: Zappos

Sunglasses: Warby Parker Sunglasses

 

Outfit #3

For the third and final look, I went with another “elevated casual’ outfit that’s great for both the week or weekend. I started with a lightweight, unlined blazer and paired it with a relaxed mandarin collar button up and some green chinos for a splash of color. As I mentioned in my color matching article, I love pairing blues and greens together and the crisp white shirt is the perfect complement. I finish it with some fresh white sneakers to add a relaxed vibe.

Outfit Details

Blazer: Brooks Brothers Blazer

Budget-Friendly Blazer: H&M Blazer

Button Up Shirt: Topman Shirt

Chinos: J.Crew Chinos

Chinos Alternative: Uniqlo Chinos

Sneakers: P.F. Flyers Sneakers

Sunglasses: Tom Ford Sunglasses

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






The #AskAW Show: Episode 02

Have a question you’d like me to answer? Ask in the comments of this youtube video or send me an email.

Show Notes & Links

Q: I’d like to find a good pair of suede Chukka Boots, but I’ve got big feet – Size 15, can you help?

Allen Edmonds - Dundee Suede

Allen Edmonds – Dundee Suede

 

Q: What can I wear with my blue suede wingtips?

Dark wash jeans 

 

Q: How can I dress nicely in really warm weather?

Polo Shirts

 

Linen Button Up Shirt

 

Chino Pant

 

Shoes

 

Q: What watches would you recommend for a guy with skinny wrists who wants a brown band?

 

Q: What do you think about the proportions of this jacket?

Fashionbeans.com story I commented on.