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.

Wool Blazers & Sport Coats

I’m sure you’ve already seen my article/video about a Navy Wool Blazer in my Wardrobe Essentials Series, riiiiiggghhht? If not, then please read and watch it first before we talk about Fall and Winter wool blazers/sport coats, because I’m going to assume we’re on the same page in regard to the differences between a blazer, sport coat and suit jacket as well as how your blazer should fit your body type as well as the finer details of what to look for in a quality blazer. Otherwise, you will probably be lost or think this article is a little anemic. There will be a few critical differences between your year-round blazers and your specific Fall and Winter wool blazers. So let’s get into them.

1. Fabric Weight

The most important difference during this time of year is the fabric weight of your blazer.

You want a much heavier wool fabric, like Harris Tweed, for three reasons:

  1. It will keep you much warmer during this time of year.
  2. The heavier weight pairs better with similar weighted fabrics during this time of year – Like your wool ties and pocket squares, wool trousers, sweaters, cardigans, etc.
  3. If it has a tighter weave, like Harris Tweed, it’ll be more durable, robust and repel water and snow better.

To get technical for a moment, a typical weight you should look for is around 12 ounces, but you can go all the way up to 16 to 20 ounces. For year-round wool blazers, I prefer a fabric weight of between 8 to 10 ounces, depending on your climate. In comparison, for hotter climates/seasons, I usually go with somewhere around 6 ounces for the fabric weight.

You’ll instantly notice the difference of fabric weights when you feel the blazer in-person. It’s a little harder to see it in in pictures, so I would suggest going to a store that carries suits to see it for yourself.

Long story short, you want a thicker wool for this time of year.

2. Color

The second difference is the colors for the time of year. Unlike the year-round wool blazers, this is the time of year where you can wear richer, more jewel-toned colors, all based on your skin tone, of course.

The best way I can describe colors is to think of the leaves changing to their fall colors and those are the colors you want for the season. So that typically means these colors:

  • Browns
  • Burgandys
  • Greens
  • Blues
  • Oranges

I went over all these colors and how to wear them based on your skin tone in my introduction article & video to this series.

3. Patterns

The last and final thing to consider for your Fall & Winter wool blazers are the patterns. Since you’ll be wearing heavier items, bold and heavier patterns work great this time of year.

My favorites are:

All of these patterns are included in my selects from various brands below.

Best Ways To Wear A Wool Blazer During Fall & Winter

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H&M Dark Khaki (Green) Blazer
J.Crew Cotton-Cashmere Crewneck Sweater in Jacquard
The Tie Bar Kingsley Attune
H&M Wool Suit Pants
Aldo Acerrassi boot
Rolex Submariner Date
Tom Ford Snowdon Sunglasses

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Topman Light Brown Wool Rich Formal Coat
The Tie Bar Chambray Shirt 
The Tie Bar Wentworth Plaid 
The Tie Bar Kingsley Attune Pocket Square 
The Tie Bar Metallic Navy Tie Bar
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Johnston & Murphy Cormac Double Buckle Monk Strap
John Varvatos Prince Sunglasses

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H&M Wool-Blend Blazer Slim Fit
Brooks Brothers Milano Spread Collar Dress Shirt
The Tie Bar Score Check Tie 
The Tie Bar Olive Green Tie Bar
The Tie Bar Southeast Plaid Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Allen Edmonds Strand Cap-Toe Oxfords with Dainite Rubber Sole
IWC Portugieser Automatic Dress Watch
Tom Ford Snowdon Sunglasses 

All of these blazers are from companies that I love. Zegna, Canali, and Brooks Brothers’ blazers have superior construction and the fit, color, and pattern are exactly what I look for in a standout blazer for my clients. For more budget-friendly options, I really like J.Crew’s english tweed sportcoats. The weight of these blazers are perfect and the solid textured colors (brown, grey, and navy) will never go out of style. For a nice camel or dark green blazer, Topman and H&M, respectively, make these nice blazers. The fabric isn’t as thick as I’d prefer, but the price point is hard to beat so I’m willing to overlook that.

$2,895 – Ermenegildo Zegna Windowpane Two-Button Sport Coat
$1,595 – Canali Tic Two-Button Sport Coat
$538 – Brooks Brothers Milano Fit Multi-Windowpane Sport Coat
$418 – Brooks Brothers Fitzgerald Fit Blue Harris Tweed Tic with Windowpane Sport Coat
$350 – J. Crew Ludlow Legacy Blazer in American Wool
$220 –Topman Light Brown Wool Rich Formal Coat
$200 – TopMan Selected Homme Navy Blazer
$70 – H&M Dark Khaki Blazer

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.

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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.

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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.

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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:

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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.