How To Wear Patterned Shirts

Whether you want to level up your business casual and weekend wardrobe or complement dressy looks, the right patterned shirt can do wonders. No matter if I’m dressing my clients formally or casually, I rely on patterned dress shirts to add both style and visual interest to whatever they’re wearing, and I’m going to show you how to do it so you look great – every time.

First, a quick word on formality.  While it’s not a hard and fast rule, in a basic sense, the bigger or bolder the pattern, the less formal the shirt is. For most of you dressing casually or in business casual, you’re home free, most patterns will definitely work. But, for some of you guys that work in more formal office environments or if you’re dressing up for a fancy wedding or evening event, keep in mind that the more subtle patterns will be much more appropriate. So now that we’ve got that established, let’s get some patterns in your life.

Stripes

Stripes can come in all manner of widths, from wide (sometimes known as Bengal stripes), to medium (pencil stripe), to thin (pinstripes) and since they tend to lean a bit more conservative, they’re also an easy place to start if you’re new to the game.

How Best To Wear Striped Shirts

As a general rule, the wider the stripe, the bolder the statement, and just like matching colors, the bolder the choice, the more simply you should approach the rest of your look. For casual and business casual looks, a simple pair of chinos or dark denim is a great option.  I also like stripes when worn with solid-colored or textured suiting and under a solid v-neck sweater with dress pants, denim, or chinos.

Checks

The world of checks is a wide one, but there’s no better way to add some instant personality to your shirt arsenal than with a few carefully chosen checked shirts.  There are many different options available, but, in my opinion, the three with the most versatility and style are windowpane, tattersall, and gingham. Both windowpane and tattersall feature types of graph patterns that can range in size and thickness and gingham goes one step further with a bolder, thicker check pattern that often combines a base color like white and one other color.

How Best To Wear Checked Shirts

As with stripes, the level of statement can vary, but my go-to rule remains, keep the rest of your look simple.  Dark-colored denim, chinos, and dress pants are the ticket, and if you’re going to dress them up, I recommend solid-colored suits and solid or subtle ties. On the tie front, I think geometrically patterned ties can look a bit too matchy-matchy with checked shirts, so be wary. Protip: for a less formal tie option, try a knit tie in a solid, complementing color. The texture and slightly less formal nature of a knit tie work really well with blazers, chinos, and denim for a dressy hybrid that’s great for business casual or a dressed-down Friday.

Geometric and Floral Prints

Now more popular than ever, print shirts are a great way to add a cool, modern edge to your casual looks and even suiting and dress clothes. Small-scale geometric prints are a great place to start if you want to keep it subtle but, I definitely recommend trying a bolder floral print too, it’s an easy, fun way to add a bit of stylish personality to your vibe.

How Best To Wear Geometric and Floral Prints

The printed shirt is all about letting the shirt do the talking, so I highly recommend denim or dark chinos in navy, tan or gray, especially if you’re going with a floral print, and finish with sneakers or loafers (I like driving mocs). Don’t be afraid to dress up a printed shirt too, pair it with a slim dark suit and some penny loafers or dressy leather sneakers for formal-but-not-stuffy settings like a cocktail party, fun summer wedding or night out. For a black belt-level move, try rocking the air tie (top button buttoned, no tie).

Plaids

When you’re talking plaid shirts, usually the pattern involves multiple colors and lines/boxes and the more things happening with the pattern (color, width, etc) the better suited the plaid will be to casual dressing. Be warned, though, it’s a slippery slope to full lumberjack hipster, so chop firewood at your own risk!

How Best To Wear Plaids

Ultimately these patterns are busy, and I recommend keeping plaids casual and subtle, so try them with denim, chinos, and shorts in solid colors, and finish them with shoes like sneakers or chukka boots. You can always “turn down the volume” of a plaid by layering it under a solid-colored sweater, lightweight jacket or pairing it with a dark-colored blazer in dressier situations.

Now that you’ve got some know-how and a few tips in your pocket, have confidence and make these patterns work for you! Your shirt rotation (and your wardrobe in general) are about to get an upgrade.

The Best Men’s White Sneakers For Every Budget

As you probably know by now, I’m a huge fan of a classic white sneaker, they’re just one of those essential items that every well-dressed man should have and wear regularly.  They’re the anchor of a solid casual wardrobe, especially during the Spring and Summer months. As I mentioned in a recent video, white sneakers aren’t one of those items that have any kind of age restriction and everyone can wear them, it just comes down to styling them correctly, with age-appropriate pieces.  Plus, the great thing is, no matter your budget, there’s a white sneaker out there for you.

The Budget-Conscious

Converse All Star – $40

Talk about classics, these guys have remained nearly unchanged since they were first introduced in the 1920’s, and for good reason, they’re simple, affordable, and versatile.  You can knock around in them all spring and summer (a BBQ, the bar, the beach, wherever) and not have to worry about wrecking something expensive.

Wear Them With

Since they’re made from canvas and are the most casual, wear them with just about everything from shorts and a t-shirt to your favorite pair of denim or chinos.

The Mid-Range

Adidas Stan Smith – $75

Also a classic athletic style from back in the day (tennis, this time around), Stan Smiths take it up a notch since they’re made from smooth leather.

Wear Them With

Obviously, they’ll work with all your casual stuff like shorts, t-shirts, and denim, but since they’re made from leather, don’t be afraid to dress them up a bit with dark denim and a polo or long sleeve button down shirt.

The High End

On the high-end/designer side, you’ll have more diverse choices. These are some of my favorites:

Common Projects Achilles – $400

Sure, $400 may seem like a lot for a pair of sneakers, but these are worth it, I promise.  Invest in them like you would your dress shoes because they’re crafted in Italy from incredibly high-quality Napa leather and are very durable.  In short, they’re well worth the price.

Saint Laurent Court Classic Sneakers – $495

If you’re looking for a stylish hybrid of Stan Smiths and Common Projects, look no further.  They also come in a bolder version if you’re looking for a little extra pop of color.

Valentino Flycrew Leather Sneaker – $695

Now, if you’re a little more adventurous and want to go with something truly unique, you definitely can’t go wrong with go with the Flycrew sneakers by one of my favorite Italian brands, Valentino.

Christian Louboutin Rantulow Leather Sneakers – $850

Ready to stand out? For the crème de la crème, and something you really won’t see on anyone else anyone else, grab these. I use them a lot with clients and they’re absolutely fantastic.

Wear Them With

These super-clean design all work really well with dark denim, t-shirts, and button downs, but the higher-end designs and nice leather are also elevated enough to wear with a dressed-down suit or blazer if you want to try a more fashion-forward look.

Now that you’ve got your white sneakers ready to go, don’t forget to keep ‘em clean! Here’s a quick video on how to do it right, it’s simple, quick and effective!

How To Wear and Match Colors Like A Pro

I know you’ve probably experienced that sense of dread as you’re standing in front of your closet, possibly pantless, definitely shirtless, thinking to yourself “How the hell do I figure out what shirts go with what pants?” or “How do I know which colors go well together?” So before you throw your hands in the air and wear your bathrobe to the office (not recommended, by the way), take a deep breath, I’ve got you. Here are a few of my foolproof strategies for wearing color; master them and in no time you’ll be looking sharp, feeling chill, and have your morning routine dialed in.

Keep It Simple

If you don’t know where to begin, I always say keep it simple. On the dressy side of things, that means starting with a solid white shirt and a neutral black, charcoal, or navy tie. No matter your suit or blazer color, a white shirt and one of the mentioned tie colors will work every time. On the casual side, the same holds true: a white shirt never fails. Whether it’s a basic button-down oxford, one dressed up with a blazer, sweater, or lightweight jacket for a night out, or a T-shirt paired with denim or chinos, the white shirt just works.

Go Monochromatic

Here’s another approach I like to use with my clients. Going monochromatic involves pairing different shades of the same color for a complete look. This is not only simple to execute, but it looks both cool and modern.

I recommend starting with blues or greys because they work best visually and are the easiest to execute with everyday pieces. By all means, throw in some subtle patterns (like in your shirt or tie) when layering to add a visually interesting element. I also like an all-black look, but the key to making it work is layering different textures/fabrics.

Consider Your Skin Tone

Our final piece of the puzzle has to do with your skin tone. Now I get asked all the time about matching clothing colors to eye and hair color and the only thing you need to know about that is this: it doesn’t matter one bit. Women pay attention to their eye and hair color when putting on makeup because certain colors can highlight their facial features. When it comes to men, this does not apply unless you’re wearing makeup. The only thing that you should consider is your skin color in regards to clothing choice.

Yellow Skin Tones

For men of Asian descent or those who have yellow tones in their skin, you’re going to want to avoid lighter/pastel versions of the following colors: tan, off-white, yellow, and orange. They’re only going to make your skin look sickly or muted. Solid, darker versions of these colors are ok, and from there, you can wear any other colors.

Brown Skin Tones

If your skin is on the brown spectrum (anything from light to dark) you want to avoid any brown color that closely matches your skin color. Otherwise, you’ll look dull and lifeless. Choose something darker or lighter from your skin and you’ll be in great shape. I highly recommend wearing colors like reds, yellows, greens, and blues, because they’ll look great against your warmer skin tone.

White or Pale Skin Tones

For those of you who burn at even the slightest hint of sunlight, you want to avoid reds, yellows, pinks, and oranges in all shades and forms. These colors are really going to bring out the pink undertones in your fair skin and make you look flushed or washed out. A good rule of thumb to follow is that “cool” colors are good.  Wearing colors like blues, greens, purples and their variations are going to look great against your skin and complement your fairness.

My Favorite No-Fail Color Combos

Finally, I’m going to share an easy cheat sheet with you, a few of my favorite, go-to combinations and how to wear them. It doesn’t matter if you’re wearing these casually or dressed up, all of these color combinations are going look great.

Navy and Brown

Both classic and modern, navy and brown go together like peanut butter and jelly.  From dark denim and a brown jacket or blazer to a navy suit with brown accents, to something as simple as tan chinos and a navy casual jacket, this combination is one you absolutely should master.  Throw a white shirt into any navy and brown combination for an easy way to bring it all together.

Blues and Greens

Speaking of rock-solid, one-two punches that work in tandem, blue and greens together are always on point. The wide range of hues gives you the option to dial up the statement level (or tone it down), depending on what shades you choose, what occasion you’re dressing for, or how adventurous you’re feeling.

My favorite ways to wear these colors together are:

  1. A navy suit, light blue shirt, and a green tie
  2. A blue oxford or t-shirt, green chinos, and brown leather belt with chukka boots

Black, Grey, and White

Simple?  Sure. Always sharp, clean, and in good taste? You bet. If you’re one of those guys who can appreciate the idea of a modern uniform or the utmost in classic simplicity, stick to this graphic combination and feel confident knowing you’re always going to look great.

My favorite outfit combos for these colors are:

  1. Grey suit, white shirt, and black tie.
  2. Black bomber jacket, white shirt, and grey pants.

Charcoal/Grey and Pastels

We’ve obviously established the awesome versatility of charcoal and grey, so it makes sense that they would also work well with pastels.  The great thing about pairing them with shades of grey is that their impact is taken down slightly. So, you get the benefit of a splash of color but you’re never going to be over-the-top preppy guy from Martha’s Vineyard or look like you’re on vacation in the Caribbean.

My favorite outfit combos:

  1. Grey suit, white or pastel shirt, and any simple dark tie (pastel shirt) or pastel tie (white shirt).
  2. Grey or charcoal casual jacket, pastel shirt or sweater, and navy pants.

I hope that was helpful and as you can see, wearing colors doesn’t have to be confusing or scary, so give it a shot!

Men’s Wardrobe Essentials: Lightweight Jackets

You know that confusing time when it’s still jacket weather but the temperatures are fluctuating from warm to cold and you’re chilly one minute and sweating the next? Yeah, it’s not easy to dress for that, is it? You’ve probably seen the word “transitional” used in and around this time relative to your wardrobe, but really it’s just a fancy word for “versatile”. With versatility and changing seasons in mind, let’s discuss a major key to a solid “transitional” wardrobe, the right lightweight jacket.

Whether you’re in bomb cyclone territory or more temperate parts of the country, the ideal lightweight jacket (or two!) is an important element because you can layer up or down depending on temperatures, all while maintaining style and a comfortable temperature. There are a million different versions in all manner of materials, but until you’ve completely nailed all the essentials, I recommend sticking to the classics for versatility, style and ease of wearing. No matter which one you choose or what the weather app on your phone is telling you, you can layer up confidently (t-shirt, collared shirt, sweater, whatever) for anything from work to a night out.

The Bomber Jacket

Also sometimes known as the MA-1 and tracing its lineage back to the uniform jackets designed for military pilots in World War II, the classic style and functionality of a bomber remains just as strong today as it was back then. Featuring a zip front, elastic waist and cuffs, and a low-profile collar, you can find stylish versions of the bomber in every conceivable material, from nylon and wool to cotton and suede. I absolutely love the versatility of a bomber jacket, and as I’ve said before, every man, regardless of age or body type, should have one in his closet.

outfit details here

Who Should Wear It

All body types and ages look great in bomber jackets – as long as it fits well – close to the body with arms and shoulders fitted like the above picture.

How To Wear It

A casual staple that’s infinitely versatile, the Bomber looks right at home with everything from a t-shirt and denim to chinos and a chambray or oxford shirt. Make sure the shoulder seams sit properly, almost exactly like how your suit jacket or blazer should fit and know that a bomber jacket that fits properly should stop right around your waist. Most bomber jackets are slightly shorter in the back, too, so don’t think something is wrong if you notice that. A longer bomber jacket tends to look odd and sloppy, so avoid it if you can.

For outfit ideas, see this article, as well as points 3 & 4 in this article/video.

The Trucker Jacket

Just like it’s close cousin the Bomber, the trucker jacket was born out of utility and remains a classic style piece to this day. Typically of shorter length and hitting around the hip/waist, the workwear-inspired trucker jacket often features a button or zip front, fabric-covered collar, and handy flap pockets on the front. I like all types of materials for trucker jackets but you’ll most commonly find them in sturdy waxed cotton or canvas (to protect against the elements), denim, and nylon.

outfit details here

How To Wear It

Another one my go-to casual recommendations, I love a trucker jacket with denim and desert/work boots. It looks stylishly masculine but still polished enough to be worn over a collared shirt without looking like you’re commuting to work on a horse.

For my favorite trucker jackets and the best ways to wear them, check out this article.

The Field Jacket

Going by many names (M65, Utility Jacket, Safari Jacket), this essential is just another example of how functional military-inspired designs still look sharp and stylish today. It’s slightly longer length should hit just past the hip and it commonly features multiple sets of pockets for extra utility when you’re on the go. The Field Jacket is a great protector against the weather yet light enough for the Spring’s rapidly changing temps, so look for it in cotton and nylon versions. Forest or Olive green colors are more traditional but I’m a big fan of navy (my favorite), darker browns or grays, as well.

Who Should Wear It

Stockier or larger men. The multiple pockets help break up your large top half and give a slimming appearance.

Who Shouldn’t Wear It

If you’re a slimmer guy and not 100% confident in how to wear this, avoid it because it’ll can make you look slimmer and like you’re swimming in pockets and fabric. I see this mistake more often than not. So when in doubt, skip it.

How To Wear It

Layer it over a cashmere sweater and an oxford or even your favorite dress clothes to add a bit of contrasting ruggedness to a polished look. Of course, it’s always perfect for your weekend morning coffee runs with t-shirts, jeans or tailored sweats too. I’d avoid wearing it with chino pants because the fabric weights are too similar and you’ll look like a 70’s action star pretty quickly. Ideally, you want something heavier on the bottom – jeans or wool trousers.

For my favorite field jackets and best ways to wear them, check out this article.

The Harrington Jacket

I’ve talked about my love of the Harrington jacket before, and for good reason, this jacket strikes that perfect sweet spot between casual and sporty and goes with pretty much anything. Look, if it’s good enough for style icons like McQueen, Elvis, and James Dean, it definitely deserves a place in your closet. The Harington blends a slight preppy edge with the functionality of a windbreaker and most often features a light cotton or nylon shell, zip-up front, and barrel button collar. Whether on the links, out and about, or heading to drinks, the Harrington has you covered. 

Who Should Wear It

All body types and ages look absolutely fantastic in a Harrington.

How To Wear It

The Harrington’s preppier look and vibe pairs perfectly with staples like chinos, t-shirts and button-ups, but it just as easily transitions to a casual evening out when layered with a light sweater, dark denim and sneakers or loafers. For more in-depth details, see this article/video.

The Denim Jacket

While it’s at home on the range or in a 50’s movie star’s vintage Porsche, the denim jacket can be just as stylish and useful to you on your own city streets. A classic for a reason, the denim jacket has seen a recent resurgence to staple status now that denim is pretty much everyday wear. While this short, button-up jacket doesn’t offer a ton of warmth, it’s vintage throwback style, when paired with a crisp white t-shirt or layered over a light cotton sweater, more than makes up for it.

outfit details here

Who Should Wear It

Everyone! It looks right at home on men of all ages and body types. The only caveat is if you’re an older man (50’s and above) you may want to avoid lighter colors, as it tends to look a little “trying to dress too young”, so stick to darker indigos or black if that’s you.

How To Wear It

Properly pulling off the Canadian Tuxedo is a very dicey (impossible?) move, so keep it simple and pair with chinos and black or dark denim, or opt for colors like grey, black, indigo, or light-washed denim. On the fit side, it needs to be tight in the arms and body and stop at the upper part of your waist, so keep it trim and short to avoid looking boxy or like a 90’s R&B music video backup dancer.

For more details, check out my more in-depth article/video here.

The Essential Business Casual Details & Outfits

To me, business casual for men’s outfits is a loose definition, but it definitely has an upper and lower range of what’s appropriate. The only true way to determine what it means is by looking at it in relation to the current dress code of the company or function you’re dealing with.

Things to avoid in business casual

Ties

There are rare exceptions, but when in doubt, go without.

Shorts

These are too casual no matter how they’re worn and I’d argue that a man shouldn’t wear shorts in 95% of situations, anyways.

T-Shirts

While I love them, they have no place in a business casual outfit.

Not Tucking In Your Shirt

The sin of all sins for a business casual outfit, no matter your body type, is not tucking in your collared shirts. Polo shirts should only be worn untucked, but the exact opposite is true for collared shirts. It just looks sloppy.

 

Now let’s go over the typical outfits and when they’re appropriate to wear.

Standard Business Casual

For most companies, whether they require a suit (maybe no tie) or a blazer or collared shirt everyday, there are two types of business casual outfits. How close the dress code is to a full suit will determine whether you should wear a jacket or not. Also, depending on the time of year, you may go for lighter or heavier weighted fabrics for your jackets and pants. Hotter = lighter.

With A Jacket

If you are required to wear a suit and tie everyday, definitely go with this one.

Sport Coat/Blazer

Here’s another article I wrote about heavier sport coats/blazers for the Fall & Winter months. Please, whatever you do, don’t wear a suit jacket in place of this. The fabric is too thin and it won’t match the fabric weight of the pants you’ll be wearing.

Oxford Button Down Shirt or Semi-Spread Collared Shirt

Make sure either of these are tucked in to your pants. Definitely wear a belt that matches your shoe color, as well.

Wool trousers, Chino Pants or Dark Wash Jeans

The more formal the dress code, the more likely you should wear wool trousers. Chinos are a little less formal or more used during spring and summer, while jeans a little less so than chinos and typically used year-round. Never, ever – unless the suit pants are a very thick wool (similar to wool trouser weight) – should you wear suit pants without the accompanying jacket.

Oxford Dress Shoes, Monk straps, Brogues, WingtipsBoots (Dress or Chukka) or Loafers

The second you’re not wearing a full suit and tie, you can basically wear anything but sneakers with your business casual outfit. I’d default to Oxfords, Monk Straps or Loafers – either in suede or leather, but any of the options above are acceptable.

Without a jacket

If the dress code or occasion is slightly more casual, you can forgo the jacket and wear this business casual outfit, instead. There’s a few small points to consider.

V-neck sweater

If the weather is too warm, then definitely swap out the sweater for a blazer from the previous section, or, if it can be more casual, go to the next outfit, instead.

Shirt

Same as the previous outfit. You can wear a tie, like in the above picture, but it’s not necessary at all.

Pants

Wool trousers or dark wash jeans. Chino pants have a fabric weight that is too light to go well with v-neck sweaters.

Shoes

Same as previous outfit.

 

Casual Business Casual

This type of business casual outfit is appropriate if there’s a pretty casual dress code normally, or the event is very informal. If you see “business casual” as a requirement anywhere, this is the least formal outfit you can wear that is still appropriate for the dress code. Anything less than this is not business casual.

Harrington Jacket 

This is one of my favorite jackets of all time and fits this outfit perfectly. Obviously, only wear this if the weather is requiring a jacket.

Polo Shirt or Oxford Button Down

I’d probably default to a polo shirt unless you knew for a fact you were going to wear the Harrington Jacket or the weather is cooler. Unless you’re a slimmer guy, an Oxford Button Down worn without a jacket on top of it doesn’t look too good. No matter what, though, make sure the polo shirt fits like a glove or you’re going to look like a goofball and if you wear the oxford, please tuck it in.

Chino Pants or Dark Wash Jeans

Chino pants are the default in an outfit like this, but dark wash jeans are just as appropriate. I’d let the time of year or weather dictate whether I went with chinos or dark wash jeans. The colder it is, the more I’d lean toward wearing the jeans over the chinos.

Sneakers, Loafers, Dress Shoes or Chukka Boots

The more classy you want to make this casual outfit, the more I’d learn toward dressy shoes.

 

That’s it! Hope this is helpful!

Men’s Leather Jackets & How To Wear Them – Bomber + Motorcycle

In this article/video, I wanted to do an update to my (4 year old!) men’s essential leather jacket story. A lot of the information in my previous article is still valid, so think of this as more of a supplement for why you should own a leather jacket instead of completely replacing it. As for the types of leather jackets I’m featuring in this video/article, you’ll likely notice that some are missing and that’s for a specific reason – I just don’t like them and they tend to not look great on most men. See the video below for an explanation of what styles I don’t prefer and why.

For the best ways to wear your leather jacket(s), check out the new video and my previous article and video here.

Biker Jacket

In my previous story, I mentioned that I didn’t like the biker style very much because they have a lot going on and should only be worn if you have a very specific rock and roll style. I still think this is true if you go with the traditional or classic-style biker jacket with the belt, chrome hardware and shiny leather. But, over the years, I discovered a slightly updated version that does away with the belt and replaces the shiny hardware and leather with matte options. Basically, this style of biker jacket removes all the things I disliked about the traditional versions, and now I’ve got to say, I’m much more of a fan.

As for how to wear them, I’d style with a t-shirt or sweater in white, black, or grey, dark wash or black jeans/chinos, and a pair of black boots. If you want to “dress it up” a bit, then pair with a casual collared shirt (leave untucked) in black, green, or burgundy, and some chinos or wool trousers.

$2395 – Burberry leather biker jacket – Burberry consistently makes some of my favorite leather jackets. You’ll pay for it, but if you can swing it, they’re totally worth the price and the fit is incredible. Remember, leather jackets are a BIFL piece.
$420 – AllSaints cargo leather jacket – all the hardware on this jacket is completely blacked out which I always prefer, but is tough to find. AllSaints’ leather jackets are worth the price and for the quality and construction, they’re a steal!
$420 – AllSaints leather biker jacket
$133 – AllSaints dark green shirt – this is the shirt Dorian wore throughout the video. The dark green color and cut of the shirt is super flattering for all shapes and sizes, especially if you’re thin or huskier.

Leather Bomber Jacket

I’ve said it a gazillion times and I’ll continue to say it, over and over again (all these articles feature bomber jackets) – regardless of your age and body type, from super thin to more rotund gentleman, every single man should have at least one bomber jacket in his closet because it’s a super versatile year-round item that can be worn a myriad of ways. Now whether you go with leather, suede or fabric options, that’s up to you. Frankly, I’d have each option, if your budget allows.

As for how to wear a leather bomber jacket, I always like to keep it simple. Pair with a crewneck sweater or t-shirt, dark wash jeans, and sneakers or boots. To make it more formal, I would pair with a white collared shirt, black tie, and wool trousers. The beauty of a bomber is that you can pretty much wear it with any kind of shirt – just pair with chinos, jeans or trousers on the darker side and you’ll never go wrong.

$500 – AllSaints leather bomber jacket – classic, classic, classic.
$500 – AllSaints leather bomber jacket in greyish blue – if you already own black, mix it up with this neutral-like color. Wear how you normally would with a black or brown jacket.
$465 – AllSaints leather and wool bomber – Dorian wore this in my Fall Shoes video and it’s such a sleek take on an all leather jacket. Super timeless and stylish.

3 Outfits Every Guy Needs

My articles and videos almost always center around a specific piece of clothing or accessory, so I thought it would be fun to switch it up and talk about 3 head-to-toe foundational outfits every guy needs. Once you have these 3 outfits, you can build an entire wardrobe around them. And here’s the beauty of them: from these 3 outfits, you can switch things in and out to add your own personal touch and truly make them your own.

Outfit 1

The first outfit is a casual one, comprised of a black polo shirt, a well-fitting pair of dark wash jeans and some white low top sneakers. This is a solid casual outfit that will always look great and put together on every man, regardless of your age or body type.

3-Outfits-Every-Guy-Should-Own-Ashley-Weston-1

$198 – John Varvatos Collection Hamptons Silk & Cotton Polo Shirt in black or charcoal (Best luxe polo shirt!)
$13 – H&M Polo Shirt Slim Fit in black (**THESE ARE THE BEST POLO SHIRTS!!!!)
$165 – J. Brand Tyler Taper Fit in slate resin (Love that the color, stitching, and hardware are similar color)
$55 – Levi’s 511 Slim Fit Stretch Jeans in dark hollow
$410 – Common Projects Achilles Leather Sneakers in white
$60 – Adidas Originals Stan Smith (colorway: white/white/fairway – Also available @ Footlocker)
$415 – Tom Ford ‘Snowdon’ Sunglasses
IWC Portugieser Automatic Watch

Outfit 2

I like to call this outfit ‘dressy casual’ because it transitions well from day to night. Throw on a leather or cotton black bomber jacket with a black t-shirt, dark wash jeans and black leather chukkas.

If you’re thin to average build, you can also wear a white t-shirt. However, if you’re a broader man that’s not in shape, and you decide to take off your jacket, then a white t-shirt will actually spotlight how big you are (and not in a good way). Also, the reason why you want to go with black chukkas is because black is the dominant color in your jacket. I went with leather chukka boots over suede and lace-up boots because the latter options won’t look appropriate for every season.

3-Outfits-Every-Guy-Should-Own-Ashley-Weston-1-2

$670 – All Saints Mower Leather Bomber Jacket in black (LOVE how minimal this jacket is – definitely a BIFL!)
$88 – Everlane Cotton Bomber in black
$60 – James Perse Clear Jersey Crew in black
$10 – H&M Crew-neck T-shirt in black
$170 – Diesel Buster 0607A Tapered Jeans (I’ve bought my fiance 3 pairs of these – they’re that good!)
$55 – Levi’s 511 Slim Fit Stretch Jeans in dark hollow
$175 – Johnston & Murphy Conard Cap Toe Chukka in black

Why a bomber over a blazer?

A bomber is a very stylish, modern alternative to a blazer that works in almost all the same occasions and looks great for every man, regardless if you’re a teenager all the way to a retiree. A younger gentlemen in high school or college, for instance, wouldn’t necessarily need a blazer, so that’s why I’m not recommending it over a blazer. If the occasion does call for a sport coat or blazer, in a pinch, you can use the jacket in my next recommendation and dress it up like I did in the picture below.

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Outfit 3

Lastly, my classic go-to formal outfit is a charcoal or navy suit with a white semi-spread collar dress shirt, black or charcoal tie, white pocket square, and oxford dress shoes. If you’re going with a charcoal suit, then pair with a black tie and black dress shoes. For a navy suit, pair with a charcoal tie, and dark brown dress shoes.

I love these two suits because it’s very easy to go formal by adding a tie or dress them down by forgoing a tie or swapping in a t-shirt instead of a collared shirt.

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$1395 – Burberry Modern Fit Wool Part Canvas Suit (charcoal)
$498 – Brooks Brothers Red Fleece Grey Suit
$115 – TopMan Grey Slim Fit Suit (alternative for warm climates: Topman Charcoal Linen Suit)
$280 – Allen Edmonds Carlyle Plain-Toe Oxfords (black or brown)
$120 – Aldo Bandolla Dress Shoe (black)
$19 – The Tie Bar Grenafaux Tie (My, hands down, favorite solid tie – go with black or charcoal)
$10 – The Tie Bar Solid White Cotton Pocket Square

Top 4 Sneakers For 2017

I want to talk about the Top 4 sneakers for 2017. These are 4 sneakers I highly recommend if you’re looking to put together an intentional sneaker collection that’ll cover you for some of the different aspects of your life. For example, working out, traveling, or just needing an everyday, lifestyle sneaker.

4. Nike Flyknit Racer

This is a great athletic sneaker because it weighs practically nothing and the woven upper makes it very breathable. Also, these are a great lifestyle sneaker that you can wear with your casual clothes because the design is so minimal and it has a very sleek silhouette.

Flyknit Racer Ashley Weston

$150 – Nike Flyknit Racer (in Black/White or Black/Anthracite/Black)

3. Converse All Star & Jack Purcell

These are classics and super easy to wear year-round. Leather or canvas options are great – and always default to low-tops because they’re easier to wear than high-tops.

Converse All Star and Jack Purcell Ashley Weston

$80 – Converse Jack Purcell Tumbled Leather Low Top (in white and black)
$65 – Converse Jack Purcell Canvas Low Top (in white, navy, and black)
$65 – Converse Chuck Taylor All Star Leather Low Top (in white and black)
$50 – Converse Chuck Taylor All Star Low Top (in white, navy, and black)

2. Adidas UltraBoost

I love the minimal design of the UltraBoost. The knit upper makes it very breathable too. You can treat these as your everyday sneakers or make them your running/workout shoes because they’re super comfortable.

Adidas Ultra Boost Ashley Weston

$180 – Adidas UltraBoost

1. Adidas Stan Smith

This one will be on my list every year until something better can replace it.

These are a great lifestyle, everyday tennis shoe. Also, they’re not expensive and relatively easy to keep clean if you give them a wipe down every week or two and don’t go hiking in them. Remember, women look at your shoes for an indication of what type of man you are. Clean white shoes = this dude’s got his shit together.

Adidas Stan Smiths Ashley Weston

$75 – Adidas Stan Smith Shoes (with either the green or navy logo)

 

Notably absent in my list are basketball sneakers because those are for a very specific group of men out there who either play basketball or are crazy sneakerheads. Some guys can pull them off really well, while others end up looking immature and silly in them.