How Should Dress Shoes Fit?

This article is part of my Men’s Clothing Fit Guide.

I’ve seen so many articles and videos taking how to get the proper dress shoe fit that are completely unnecessary and just create more useless work and steps for the poor readers. Of course, if you ask a shoemaker or shoe salesperson about what goes into fitting for a pair of dress shoes, they’ll tell you about the painstaking process you must endure as they pull out their Brannock device and start measuring the length of every toe hair in relation to the current barometric pressure. As someone who dresses and fits men for shoes as part of my career, it’s all hogwash.

Never once, in all my years, with all my clients, have I ever needed to get an exact measurement of their feet – and this is because the brands and manufacturers don’t work this way. Their sizes aren’t universal and can vary wildly between brands. So a 9 in one brand might fit the same as a 10.5 in another brand. Each one is different, so it’s great that you know your right foot is 10.236 inches long by 4.789 inches wide, but that really doesn’t matter unless you’re getting custom made shoes.

So what you have to do is try on dress shoes and figure out how to get the best fit in that style/brand. Let me show you how.

Before Trying On Dress Shoes

You should know and do these few things before trying on dress shoes.

1. Know Your General Shoe Size

I’m assuming you’ve worn shoes before and have a general idea of your size? Great! That’s all you need. Like I said earlier, since each manufacturer has different fits and sizing for their shoes, it’ll all be trial and error anyways. The thing you want to do is get in the ballpark and use that as a starting point.

2. Dress shoes should fit perfectly the first time you try them on

If they don’t, they’ll never fit. Leather, especially in dress shoes, will stretch very, very little, so “working in” a pair of dress shoes is not going to happen and will be a waste of your time and money. One of the worst things ever is wearing a pair of uncomfortable shoes – as a woman, I know this all too well!

3. Your feet swell throughout the course of the day

So, if you can, try on shoes in the afternoon. This way, you’ll get the most realistic size and fit of the shoes.

4. Your feet are not the same size

Make sure the shoes fit your larger foot first, not the smaller one. Slightly too big is not uncomfortable, slightly too small is very uncomfortable.

How To Try on Shoes

When you’re trying on shoes, here’s the things to do and look out for.

Socks

Wear the type of socks that you will normally wear with these shoes. In other words, don’t wear your thick woolen socks, or your super thin ankle socks when trying on dress shoes.

Length

If you feel ANY bunching in the toes or feel the shoe pressing against any of your toenails, they’re too short. I see some places talking about your toes grazing the front of dress shoes – this is not correct.

Your feet shouldn’t be touching or grazing anything in the front. If they’re grazing, that means when you walk, your toes will be jammed into the front of the shoe, because your feet will shift slightly forward as you walk, which is very uncomfortable. Either go up a half size and if that doesn’t fix the problem, it might be a style or width issue. So try a different style or a different brand that makes the same style. Luckily, with dress shoes, they’re pretty darn similar, so you’ll find an equally great one, I promise.

Width

The shoe should not be putting any pressure or squeezing on the sides of your foot – anywhere. If you feel anything like that, you may need to go up half a size and see if that fixes the issue. If it doesn’t, you can see if they make a wider size in the same style. If they don’t, then try a different style or brand. Some brands are wider than others.

On the flip side side of that, you also shouldn’t have any room on either side of your foot that allows your foot to move left or right when it’s laced up. If this happens, go down half a size and see if that fixes the issue. If not, you can ask if they have a narrower width in this shoe. If not, you may need to try a different style or brand.

The average man has a medium width of D. If a brand doesn’t specify a width, which most of them don’t, this is probably the width they use. Again, though, a brand’s definition of a D width varies, so watch out for the differences. A narrow width is a B, a wide width is E and an x-wide width is 3E.

If your foot falls between a B and a D, go with the larger width.

I see some places saying that if they’re lace-up shoes, like an Oxford Dress Shoe (Which they almost always should be, if they’re dress shoes!), you should not be able to tie the laces so tightly that the two edges of the shoe meet. I don’t adhere to this advice because some of my clients just have less meat than others on the tops/profile of their feet and when this happens, it’s not a problem. As long as the shoe fits everywhere else, I wouldn’t about this part.

Heel

If you have the width and length in check, this shouldn’t be an issue, but just in case: You want a little bit of space between your heel and the shoe, but not too much. My one finger test for sneakers is not applicable here. They should fit a little snugger than tennis shoes do in the heel, but should not be pressing against your heel as to be uncomfortable.

Lace up both shoes and take a short walk in them. There should be little to no slippage in the heel. If there is, they’ll create blisters on your heel and that’s not fun.

Also, since I hear this complaint a lot from guys – If there’s anything like a seam or stitching rubbing against your heel, don’t get those shoes. This is mostly typical in cheaper shoes. This area will never “break in”, so if something is rubbing against your heel when trying them on, it’ll never go away, so stay far away from them unless you like blisters on your heels!

The Best Dress Shoes For Men

See my Men’s Wardrobe Essentials – The Oxford Dress Shoe for my picks.

The Dark Wash Jean

Jeans, Denim, Blue Jeans, whatever you call them – the bottom line is that they’re a staple in every man’s wardrobe. But that doesn’t mean most guys know how to choose the right pair.

Every day, I see looks of dissapoinment slapped across people’s faces as the men in their lives waddle around in poopy-pants, flop about in the moo-moo version of jeans or show off their twig and berries.

Let’s fix this.

Have questions? Curious what others think?

Join us in the comments section of the video above.

Every single man, no matter their size, age or body type should have a few pairs of dark washed jeans in their closet. They work for nearly all occasions outside of a formal setting and look good with virtually everything- especially my list of men’s wardrobe essentials. They’ll never steer you wrong and are likely the pants you’ll wear a majority of the time.

The 5 Aspects Of Jeans

1. Wash or Rinse

This dictates how light or dark the jeans are as well as how they’re treated. Light wash = lighter colored. Dark wash = dark.

My preferred wash is dark blue, sometimes called indigo, depending on the brand.

Because of the title of this article, you know I’m recommending that you own dark wash jeans. The reason is because this wash looks great on everybody, hides skinny or thicker legs better than any other color and can be dressed in a casual or less-casual way. I love them so much that I put them on every single one of my clients.

2. Style

This is also called the “cut” and sometimes also called the “fit” of the jeans. Depending on your body type, you should be wearing a certain style. We’ll get into that in a minute, but the most common styles are (in order of slimness):

  • Skinny
  • Slim
  • Straight
  • Boot Cut
  • Relaxed

3. Size

The waist and inseam (leg length) measurements of the jeans. Ex: 32×32 (inches).

If you’ve seen my Fit Guide, you know appropriate jeans sizing, but here’s a quick refersher:

  • They should fit your waist without needing a belt. They can even be slightly tight, as denim will loosen as you wear them.
  • The inseam (length) should leave a slight or full break where they meet your shoes. Anything shorter will look odd and anything longer will bunch at your ankles and throw off your proportions.

4. Denim Type Or Fabric Blend

Denim material can be blended with a variety of other fabrics. Some jeans may have two to three percent spandex and others might have polyester blended into them.

A quick thought if you go with spandex blends:

  • Spandex blends, while a little more comfortable and forgiving in the thighs, tend to stretch out and not retain their shape as well as 100% cotton blends. I’ve definitely seen some “poopy pants” as a result of this.

It’ll depend on what you prefer, I can go either way on this – some of my recc’s below are blends, some are 100% cotton.

5. Fit

I get asked all the time “How should men’s jeans fit?”

Here’s the the trifecta of how your jeans should fit, regardless of age or body type:

  • You should be able to pinch a minimum of 1 inch of fabric, but no more than 1.5 inches on either side of the thigh.
  • They should fit your waist without a belt.
  • They shouldn’t be too short or too long – having a slight or full break. 

Check out my Fit Guide for more in-depth info.

The Best Dark Wash Jeans For Your Build

A quick note about your height: It doesn’t matter. My clients range in size from 5ft 3in to almost 7ft and I’ve never put them in different jeans because of their height. These are the best jeans for short men, tall men, medium-sized men and so on. The only thing that matters is your build: slim/regular or larger.

Slim or Regular Build

You’ll want to get a “Slim” fit. Slim-fit jeans tend to slightly hug the thighs, knees, and calves while tapering down from your knee to ankle.

A lot of my slim & regular built clients initially believe this style will make them look too skinny. This couldn’t be further from the truth. It’s just that they’re used to wearing super baggier clothes to try and hide their slimness, which, coincidentally, just makes them look slimmer. A proper fitting pair of jeans just looks right, regardless of your build, and doesn’t make you look one way or another – I promise.

Things to avoid:

  • Don’t make the mistake of thinking “Skinny” fit is the same as “Slim” fit. “Skinny” fit jeans are usually skin-tight and not appropriate
  • Avoid “Straight Fit” jeans. Like the name implies, the leg of the pants are looser and will be cut straight down from the knee to ankle. This cut will look terrible on you. 
  • If you can pinch more than an 1.5 inches of denim on either side of your thighs, you need to move down to a slimmer cut or get the legs taken in. If you can avoid it, don’t rush to the tailor. Try a size down first or another brand. This is costly for a tailor to do. Having too much fabric on your thighs will make you look smaller, shorter or wider than you are.

Designer

I’ve personally worked with and touched each pair of these jeans (in all sections) and they’re awesome. The fit is very accurate, the pocket placement and stitching is great. Diesel runs a little larger in the waist, so go down a size (ex: if you’re a 34 waist, get a 32).

Tom Ford Slim-Fit Stretch Indigo Denim Jeans
RRL Slim Fit Selvedge Jeans
JBrand Tyler Taper Fit in Rasalas
JBrand Taper Tyler Fit in Blue Hood
Diesel Buster Jeans

Budget Friendly

I love these because the quality in relation to the price is very good and you can never go wrong with a classic like Levi’s and I love Uniqlo’s wash and they also offer free hemming!

Uniqlo Stretch Selvedge Slim Fit Jeans
Levi’s 511 Slim Fit Stretch Jeans

Larger Build

The classic “Straight-Leg” fit is perfect for you. No matter a man’s build, but especially in your case, it’s all about balancing your body’s proportions to make sure your bottom half complements your upper half.

There are a few great brands out there that offer straight-legged jeans with a slightly roomier thigh area which will hopefully solve your frustrations with finding jeans that fit properly.

Things to watch out for:

  • Avoid any cut of jean (all pants in general, for your build) with a taper in the legs. A taper will make you look really top heavy.
  • If you can pinch more than an 1.5 inches of denim on either side of your thighs, you need to move down a size, go to a slimmer cut, try a different brand, or get the legs taken in by a tailor. Don’t get the legs taken in if you can help it, it’s costly for a tailor to do. Having too much fabric on your thighs will make you look wider than you are and completely throw off your proportions.

Designer

The wash, quality and fit of these are great and I use them all the time for my larger clients because it makes them look really sharp.

AG Graduate Jeans
JBrand Kane Jeans 

Budget Friendly

Just like I said for the slim to regular built options in this category: I love these because the quality in relation to the price is very good and you can never go wrong with a classic like Levi’s and Uniqlo’s wash is great and they offer free hemming!

Levi’s 514 Tumbled Rigid Jeans
Uniqlo Selvedge Straight Leg Jeans
Gap 1969 Straight Fit Jeans

3 Ways To Wear

Ashley-Weston-Dark-Wash-Jeans-Look-1-Full

Levis Sunset Pocket Tee
JBrand Tyler Taper Fit in Rasalas
Allen Edmonds Wide Basic Belt
Vans Authentic Sneakers

Ashley-Weston-Dark-Wash-Jeans-Look-2-Full Ashley-Weston-Dark-Wash-Jeans-Look-2-Detail

Brooks Brothers Suede Barracuda Jacket
J. Crew Garment-Dyed Henley
JBrand Tyler Taper Fit in Rasalas
Allen Edmonds Wide Basic Belt
Vans Authentic Sneakers

Ashley-Weston-Dark-Wash-Jeans-Look-3-Full Ashley-Weston-Dark-Wash-Jeans-Look-3-Detail-2 Ashley-Weston-Dark-Wash-Jeans-Look-3-Shoes

Modern Fit Travel Tailoring Virgin Wool Suit
Brooks Brothers Red Fleece Spread Collar Sports Shirt
JBrand Tyler Taper Fit in Rasalas
The Tie Bar Knitted Tie
The Tie Bar Cotton Pocket Square dark Charcoal Tipping
Johnston & Murphy Fielden Cap-Toe Dress Shoe
IWC Portuguese Automatic Watch

Outfit Inspiration

 

The Gray Notch Lapel Suit

If you’re over the age of 15 and don’t own a 2 button Gray Notch Lapel Suit (sometimes called medium gray, grey or charcoal), we have to rectify this – immediately! It is the most important suit you’ll own and is the quintessential foundational piece that will work for you no matter your age or body type.

FashionBeans.com put my love for a gray notch lapel suit perfectly:

“It can take you from your first interview all the way to your final address to the board – including all those weddings, funerals and formal events in between. There is nothing it can’t do. Even if you’re only going to need your suit for weddings/funerals/special occasions, this is still the one suit you should always have in your wardrobe.”

The suit is a perfect blank canvas from which to experiment with. You can imbue your personality easily into an outfit via colorful shirting and accessories. If you’re going to play with shirt colors outside of white or light blue, keep the tie a basic/neutral color – black, blue or gray. Same goes for a colorful tie, keep the shirt neutral – white or light blue.

“But a Gray Suit is Boring”

A lot of my clients say this when I first start working with them and building their wardrobe. The reason we choose gray is because it is a neutral color and works with everything in virtually every occasion. If you want colors and/or to spice it up, it can easily be done with the colorful & patterned accessories and shirting. There’s a reason painters start with a white canvas and not a colored one, because you can make it your own!

The classic rookie mistake is thinking that suit colors = more fashionable or stylish. Menswear is all about the details. So leave the large pieces “boring” and spice up an outfit with subtle details and punches of color.

Trust me on this one.

What is a ‘notch lapel’?

It’s the style of lapel that has a little “notch” on each side of the lapel. See the below graphic for the different lapel types. You want a Notch lapel because a Peak lapel is very aggressive and doesn’t work on everybody and a Shawl lapel should never be part of a suit. A Notch lapel is as classic and timeless as it gets.

lapel types

How Many Buttons?

Two buttons, nothing more, nothing less.

Sometimes you’ll see 3 button suits and 1 button suits, but trust me, you NEED a 2 button suit because it never goes out of style, every other variety will come and go as fashion dictates.

Vent Type?

Ideally, you’ll want to go with a double vent. This style of vent has been around for quite a while and is flattering on every body type. With that being said, a single vent is not a poor choice, but it’s definitely second in my book. Just make sure that, no matter what, you never go with a suit that has no vent.

suitvents

Can I Break This Suit Up Into Separates?

My suggestion for now, is to avoid breaking this suit up unless you really understand fabric weights and texture pairings.

I see a lot of sites saying that a gray suit is great because you can break it up – wearing the pants and jacket separately with other pieces – like jeans.

While this can work sometimes, in my experience, pairing suit items with other non-suit clothing, like jeans, looks great on camera, but really weird in-person if the fabric is too lightweight. You should really know what you’re doing to pull this off. If there’s any doubt, go without.

Fabric

Depending on how much you’ll be wearing this suit, I’d highly suggest getting a wool or wool-blended suit because it’ll last much longer than non-wool or polyester blends and just looks better and will be more comfortable.

It’s also important that your suit not have too much of a sheen or shine to it. You can tell a cheap (or really tacky) suit by how shiny it is. Don’t be afraid to compare suits while at a store to see which ones are more matte finished.

How Should My Suit Fit?

Fit is the most important part of a suit. Head over to my Suit Fit Guide and see how every suit you own should fit.

The Best 2 Button Gray Notch Lapel Suits

Budget Friendly

Topman Grey Twill Cotton Slim Fit Suit Jacket
J.Crew Ludlow Suit in Worsted Wool

If you’ll be wearing a suit less than a handful of times a year and/or are budget-conscious, I’d go with Topman’s Slim-Fit or Skinny-Fit suits or J.Crew’s Ludlow wool suit. Don’t let the horrible image of the Topman suit fool you, it looks much better in person. For the price, they’re constructed well and as long as you make sure the fit is spot on, it’ll look great.

Designer

Emporio Armani Single Breasted Suit in Worsted Wool
Z Zegna Gray Super 110 Wool Suit
Brooks Brothers Red Fleece Grey Suit Jacket 

My preference, if you want high quality, is to go with Emporio Armani, Z Zegna, or Brooks Brothers wool suits. My clients have topped GQ and Esquire’s “Best Dressed” lists in these and I use them often because the construction, fabric, and overall quality is impeccable and well worth the investment.

3 Ways To Wear

Ashley-Weston-2-Button-Gray-Notch-Lapel-Suit-Full-LengthAshley-Weston-2-Button-Gray-Notch-Lapel-Suit-Detail-Short-Edge-650

Brooks Brothers Red Fleece Grey Suit Jacket 
Brooks Brothers Red Fleece Grey Suit Trousers
Brooks Brothers White Milano Fit Spread Dress Shirt
The Tie Bar Grenafaux Black Tie 
The Tie Bar Solid White Cotton Pocket Square 
IWC Portuguese Automatic
Allen Edmonds Carlyle Dress Shoe

Ashley-Weston-2-Button-Gray-Notch-Lapel-Suit-Look-3-FullAshley-Weston-2-Button-Gray-Notch-Lapel-Suit-Look-3-Detail

Brooks Brothers Red Fleece Grey Suit Jacket 
Brooks Brothers Red Fleece Grey Suit Trousers
Armani Exchange Pima Crew Tee
IWC Portuguese Automatic
Allen Edmonds Carlyle Dress Shoe
Brooks Brothers Calfskin Belt

Ashley-Weston-2-Button-Gray-Notch-Lapel-Suit-Full-Length-Look-2Ashley-Weston-2-Button-Gray-Notch-Lapel-Suit-Look-2-Detail

Brooks Brothers Red Fleece Grey Suit Jacket 
Brooks Brothers Red Fleece Grey Suit Trousers
Brooks Brothers White Milano Fit Spread Dress Shirt
The Tie Bar Grenafaux Satin Dot Tie
The Tie Bar Silver Shot Tie Bar
The Tie Bar Solid White Cotton Pocket Square  
IWC Portuguese Automatic
Allen Edmonds Carlyle Dress Shoe

Outfit Inspiration

Graphics: FashionBeans | Model: Michael Tribby

Chambray Shirt, Sport Coat, Chinos, and Dress Shoes

The casualness of a chambray combined with the sharpness of a sport coat is a guaranteed to turn heads in the office or at any wedding. Wear an indigo button-down chambray shirt, a grey wool sportcoat, blue chinos, and black oxford dress shoes. Spice things up with a lively pocket square and a simple plaque buckle belt.

 

Designer Options

Budget-Friendly Options

 

The Holiday Party Series – Part 3: How To Dress For A Family Party

In Part 1, How To Dress For The Office Party, we went over what to wear and how to act at this year’s formal or informal work party. In Part 2, we covered How To Dress For A Friend’s Party. In this, the final post of the series, we’re going to go over how to dress and proper etiquette for a family holiday party.

If you’re going to your in-laws or (maybe) future in-law’s holiday party, your girl will use this as an opportunity to show you off to the people who’s opinion probably means the most in her life. If you show up looking like a slob and her family is similar to most, there’s going to be gossip. Yes, it’s not the end of the world to you, but to your girl, it might as well be. Trust me on this. How you’re presented to the family matters a lot to the woman in your life. So it’s your job to be her arm candy this time.

If you’re single, you’ll likely be with your family. So yes, you’re not there to show off to your potential future in-laws, but you should at least want to show your family that you’ve got (some of) your shit together.

H&M Black V-Neck Merino Wool Sweater, $50
Zara White Plain Shirt, $50
Topman Grey Check Ultra Skinny Fit Suit Pants, $75
H&M Leather Dress Belt, $20
Allen Edmonds Park Avenue Cap-Toe Oxfords, $395

Pair a black v-neck sweater over a crisp, white dress shirt. Tuck the shirt into a pair of charcoal wool pants. I don’t recommend jeans because they’re too informal when you’re trying to make an impression – regardless of the audience.

Just like I recommended for How To Dress For The Office Party, finish everything off with a black belt and dress shoes.

Tips & Etiquette

  1. You should never show up to a family function empty-handed. Grab a bottle of $10ish Merlot (red wine) and present it to the host(s) when greeting them.
  2. As soon as you enter the party, greet each person. If you haven’t met them before, introduce yourself, and tell them who you are in relation to the family. Example: “Hi, I’m Daniel – Sara’s boyfriend.”
  3. After greetings have been exchanged with everyone, ask the host(s) if there’s anything you can lend a hand with.
  4. Once the meal has concluded, don’t ask, just walk over to the kitchen and start putting things away or cleaning up or doing the dishes. And yes, they’re going to tell you it’s OK and not to worry about it. But you just keep doing it anyways. The in-laws or future in-laws will especially love you for this, and you’ll win major brownie points for years to come. If you’re at your family’s place, your Mom or Grandma will appreciate this just as much.
  5. When it’s time to leave, if you came with your girl, put her coat on first, in plain view of everyone else. She might not know it yet, but she’ll love the family watching you attend to her.
  6. Say goodbye to the oldest people first and then down the lineage line until you say goodbye to the hosts last. You’ll thank the hosts again for having you over and then leave the party immediately.

The Holiday Party Series – Part 2: How To Dress For A Friend’s Party

In The Holiday Party Series – Part 1: How To Dress For The Office Party, we went over what to wear and how to act at this year’s formal or informal work party. In Part 2 of the series, we’re going to discuss how to dress for your friend’s holiday party.

A friend’s party is usually a more relaxed, but that still doesn’t mean it’s time to pull out the sweatpants and hoodies.

If you’re single, the holidays are a perfect time to meet someone special – for the night, the month, the year, or for life. And showing up like the well-dressed gentleman that you are, definitely helps your chances.

If you’re attached, your girl is going to love watching the other women ogle you from afar. I know that when someone looks at my man, I always think, “Yeah, that’s right, keep looking – he’s with me!” Any woman can appreciate a well-dressed man and they will, whether you’re attached or not.

Topman Dark Green Marl Slim Fit Sweater, $35
Brooks Brothers Non-Iron Regent Fit Mini Pinstripe Dress Shirt, $92
JBrand Tyler Taper Fit in Rasalas, $228
H&M Leather Dress Belt, $20
Allen Edmonds Park Avenue Cap-Toe Oxfords, $395
Topman SELECT Homme Grey Salt and Pepper Wool Rich Suit Jacket, $220

Throw on a dark green v-neck sweater over a crisp, light blue dress shirt. Leave the top 2 buttons undone and make sure the collar tips are tucked underneath your sweater.

Finish with a pair of slim, dark wash jeans. Avoid jeans that have whiskering, fading, or holes because they’ll make your entire outfit look sloppy.

Don’t forget to add a black belt (making sure the buckle isn’t too large) and black leather dress shoes to complete the look.

Another option is to pair the above outfit with a sports coat. If you go this route, add a pocket square to finish it off. Remember: It’s all about the details.

If you missed Part 1 of The Holiday Party Series: How To Dress For The Office Party, I talked about the thing that’ll make or break this outfit is whether you’ve layered properly. So keep those layers on the thinner side!

 

Tips & Etiquette

  1. Bring a nice bottle of wine to thank the host/hostess for throwing the party.
  2. Bring a few business cards, just in case.
    You never know who you might run in to.
  3. Introduce yourself to every person in the room.
    Avoid only talking to the people you know. It’s not weird or inappropriate to go up to strangers at this party because they were invited by your friend/host, just like you were. So use the fact that you have a mutual friend to introduce yourself.
  4. Before leaving, make sure to say goodbye to the host(s) as well as the people you spoke with that night.
    In the adult world, it’s extremely rude to leave without saying goodbye.

The Leather Jacket

This post is part of my Men’s Wardrobe Essentials Series. In the series, I give my tried-and-true men’s wardrobe essentials/basics/must haves that every guy, whether a teenager, in their 20’s, 30’s and well past their 50’s should own in order to be a classic, stylish, well-dressed man.

For well over 70 years, leather jackets have represented individuality and a rebellious, manly side throughout American history. Marlon Brando, The Ramones, WWII fighter pilots, and Springsteen all come to mind when I think of leather jackets. A well-made leather jacket is an essential addition to a man’s wardrobe because it will never go out of style, can be dressed up or down, will generally last a lifetime and fit like a second skin.

Watching a man put on a leather jacket is like watching a prize-fighter standing over his opponent after he’s been knocked down. There’s just something about it that harkens back to a classic, badass, bygone era.

What Type Of Leather Jacket Is Right For You?

There are many different types of leather jackets available, some better than others. The biker jacket, what Marlon Brando is known for, is what usually comes to mind when thinking about a leather jacket. As iconic as this jacket is, I don’t recommend it for most guys. The buckle straps, zippered cuffs, and buttoned collar and lapels are a bit much in my opinion. Unless you’re going for the ’50’s greaser or heroin-chic rockstar look, it’s best not to go this route. It often looks much better in print or on the screen than it does in person.

If you like the classic ruggedness of the biker jacket but want a cleaned-up version, the motocross jacket is perfect for you. It has a tabbed collar and less… stuff all over it, which makes it much more versatile. I prefer this style over the biker jacket because the clean design won’t add additional bulk to your frame, so it’s a great choice for all body shapes.

My hands-down favorite of all leather jackets is the bomber style jacket. It has a clean, timeless body style and the elastic, ribbed cuffs, collar, and waist allow the jacket to hug your body nicely, while adding more comfort than the more traditional styles. The leather on these jackets is usually very soft and supple compared to the other styles, so it makes for a perfect everyday type of jacket.

Best Ways To Wear It

The Biker Jacket

If you go the biker jacket route, I highly recommend this AllSaints ‘Conroy’ leather biker jacket ($670). It has all the classic biker details and an awesome slim fit, which is important since you don’t want it to add bulk to your frame. I’ve personally worked with this jacket, and like all of AllSaint’s leathers, the quality and attention to detail is exceptional. The jacket a steal at this price.

Going on a date? Pair with a white button-up shirt, wool trousers, and lace-up leather shoes and watch her salivate the whole night. Switch out the dress shirt with your favorite t-shirt and a pair of dark washed jeans for beers with the guys.

The Motocross Jacket

I’m recommending this Zara jacket for its awesome fit, super clean design, and perfect cognac shade of brown. You may be wondering why it costs less than $100. That’s because this is actually a synthetic leather jacket. But I can assure you, no one will notice. If anything, this jacket is softer, both in feel and in the hit to your bank account than real leather, which is a plus in my book. A brown jacket pairs well with shades of blues, so go with a light blue striped dress shirt, solid navy tie, light brown v-neck sweater, and a pair of dark jeans and brown dress boots to pull this awesome look off. Nix the v-neck sweater if it’s a little warm out or you tend to run warm-blooded.

The Bomber Jacket

If you want something that looks great, is super versatile as well as comfortable, then look no further than the bomber jacket. Whether going out at night or running errands during the day, I’d pair this jacket with a white t-shirt, charcoal or dark brown wool trousers, and lace-up black leather boots. You’ll look put together and not like you’re trying too hard.

Final Thoughts

In my opinion, a well-made leather jacket is an essential addition to a man’s wardrobe because it will never go out of style, can be dressed up or down, will generally last a lifetime and fit like a second skin. When you throw one on, like a well-tailored suit, it’ll make you feel and look better. You’re not just investing in a leather jacket. You’re investing in yourself. Remember that and let’s see those leather jackets!