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.

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!

Series Intro & How to Match Clothing Colors To Your Skin Tone

In this series, I’m going to show you the must-have Fall and Winter items that every well-dressed gentleman should own. That means I’ll be talking about:

  • Boots and Shoes
  • Coats & Jackets
  • Shirts & Sweaters
  • Suits
  • And various Accessories

Like always, I only recommend products that I’ve personally touched and worked with – in all budget ranges. I’m fortunate in that I get to touch hundreds of menswear items a week, so when I say something is great, it’s not because I got paid to sell you a bunch of cheap [email protected]*t like everyone else – it’s because I have actual experience with these items.

This series is a supplement to my Men’s Wardrobe Essentials Series. In that series, I covered the year-round essentials that you should have in your closet already. If you haven’t read/watched those articles and videos, do that first so we’re on the same page.

The Best Colors & Patterns For The Season

fall-winter-colors-patterns-men-ashley-westonSince I don’t want to go over colors and matching them in every single video in this series, let’s talk about Fall and Winter colors and patterns and how to match them to your outfit and skin tone.

The appropriate colors for this time of year are:

  • Mid to darker greens
  • Shades of browns (camel to dark brown)
  • Shades of blues (light chambray to navy)
  • Shades of gray (light, medium and dark)
  • Burgundy and wine colors
  • Darker or “burnt” Orange

As for patterns, this is what I like to call “plaid season”. It’s the best time of year to wear plaid because its more visually heavy and pairs nicely with the heavier clothing you’ll be wearing, like sweaters, wool coats and wool trousers. For outerwear and Fall/Winter suiting, I love a good windowpane, as well.

HOW TO Match & wear COLORS BASED ON YOUR SKIN TONE

If you’re darker skinned, this is less of an issue because those colors look great on you. But if you’re pale or yellow-toned, this can be a disaster if you don’t know what you’re doing.

PALE or Yellow Skin

If you’re pale or yellow skin toned, make sure that your camel, burgundy, or burnt orange pieces are an outer layer and not a base layer. Let me show you what I mean.

You’ll notice in the below photo that I have my pale model wearing a camel sweater. But you’ll also hopefully notice that there is a white ring of a t-shirt sticking out from under the collar.

This is VERY important because that little sliver of white provides separation between the skin and sweater. The camel color would completely wash out his skin tone and make him look sickly if it wasn’t there. It’s much more apparent in person than images, too.

fallwinteressentialsovercoatcamelsweaterashleyweston

Below is the same model wearing a burnt orange sweater, but you’ll notice that I have a gray plaid shirt under the sweater to provide that necessary separation of the sweater from his skin. If that wasn’t there, the orange would bring out the pink tones in his skin – which would make him look red and flushed.

orangesweaterplaidshirt-ashley-weston

And lastly, going back to my white sneaker article/video, I styled my model in a burgundy bomber jacket with a black t-shirt. The shirt provides the necessary visual separation to not bring out the pink tones in his skin.

If I had him in a black jacket and burgundy t-shirt, instead, he would look oddly red-faced. This combination, though, would look awesome on someone with darker skin.

burgundyjacket-2

So to recap: If you have a pale or yellow skin tone and want to mix Fall/Winter colors into your wardrobe, just make sure it’s an outerwear piece with visible neutrals (white, grey, black, navy) underneath.

DARKER SKIN

Now, if you’re darker skinned, you can still follow the pale/yellow skin rules above because it’s the classic way to wear color and looks good on everyone. So when in doubt, wear your statement color as outer layers. But with darker skin tones, you have the added advantage of being able to wear all these colors in your shirts and sweaters and then have neutral outer colors because the contrast looks great with your skin tone.

Here’s some examples of outfits that look great on darker/warmer skin tones that would look horrible on a guy with yellow or pale skin:

darkerskintoneoutfits-ashley-weston2

Just do me a favor, though. Don’t go overboard with color. Have one standout color in your outfit and then pair it with neutrals everywhere else. When you start throwing burgundys, greens, blues and browns all in one outfit, it’s just too much going on.

How To Wear PLAIDS AND PATTERNS

It’s a great time of year to incorporate them into your wardrobe. I prefer to keep the plaids to collared shirts because it looks good on everybody and is really hard to mess up. You can wear them on their own, with the sleeves rolled up, or throw on a nice solid colored sport coat, bomber or trucker jacket over it and the shirt will look great.

As I mentioned earlier, I also love a good windowpane. This looks great on pants, suits, sport coats/blazers and overcoats.

The key to wearing patterns is to make sure the rest of the items in your outfit – pants or jacket/sweater/coat are solid neutral colors. It’s when you start mixing patterns that’ll get you in trouble real quick.

So pick an item in your outfit (normally a shirt, sweater, jacket or coat) for a pattern and then have everything else be a solid color. And also make sure that just like with your ties and pocket squares, you want a color in your plaid to be a similar shade of one of the colors in your pants or jacket/sweater. Then you’ll have a nice, classy and cohesive look.

My Favorite COLOR COMBINATIONS For The Season

Here’s some color combinations I love and use with my clients during this time of year:

  • Green and blue
  • Gray and brown
  • Blue and brown
  • Burgundy and blue
  • Burnt orange and blue

These are my go-to colors and if you stick to these combinations, you’ll look sharp and timeless during this season.

So without further adieu, let’s get into the Men’s Fall and Winter Essentials.