When you think herringbone you probably think—well if you’re like most people you probably think—‘Fabric.’ While you wouldn’t be wrong, herringbone, like all people and things worth knowing, has got a little history. And by that we mean, a little baggage.

Since you’re not dating herringbone, this is totally fine.

If nothing else, it gives you something to talk about at parties when people ask you about the killer shirt you’re wearing.

Instead of simply saying, “Hey yeah thanks, it’s some fabric!” You’ll be able to swirl your martini glass and say, “Herringbone, actually, very common in twill or tweed weaves.” When knees have stopped knocking together at your sartorial prowess, here’s what will happen next:

“W-hy,” a still woman party-goer will ask, “W-why is it called herringbone?”

At this point in time, feel free to live the dream and do your best Humphrey Bogart, “Well doll…” (regardless of gender calling someone doll in the manner of Humphrey Bogart is universally hilarious and awesome).

Next you’ll say, “Notice how the weave itself is a v-shaped formation? Come on, don’t be shy, take another step over here and get a real good look.” At that point, the whole room will fall silent as a throng of smitten folks will step towards your custom made herringbone shirt. You’ll whisper over your glass or perhaps after taking a drag on your cigar (if that’s what you’re into), “Back in the day, they thought these v-shaped weave patterns looked like little fish bones—herringbones, if you will.”

(kinda like fish bones—right…?)

At the mention of bones you will immediately earn all manner of street cred. Not only will those with a passion or sartorial history bow before your superior knowledge, but even the Goth gang’s hearts will go pitter-pat when you whip out the word ‘bones.’

And the notoriously hard please fashionistas won’t care one way or the other—they’ll just be thrilled you’re wearing a unique product tailor-made to suit you. Well played, Mr. Bogart well played.

Not all cotton dress shirts are created equal and you’re likely to discover this the hard way if you don’t know what to look for. OK, seeking out higher quality cotton dress shirts may be a bit more expensive, but considering how many hours we spend in dress shirts, it’s more like an investment in the future. Y’know—like college or good scotch (see Johnnie Walker Red/Black label below).

So here’s what you should be investing in:

* Strong yet soft: Higher quality shirts will be two-ply, not single-ply. This makes the fabrics stronger, but also softer, less rough and scratchy. You can save that for your 5:00 shadow.

* Count your threads: No, not literally. Quality cotton dress shirts boast their thread counts themselves. Thread counts of 80s and higher make finer, softer, and ultimately better looking shirts.

* A stitch in time and all that: Take stock of the seams on the shirt. Cotton dress shirts that are high quality will have straight stitching and evenly spaced stitches. Irregularity in stitching is a big no-no.

* Details make the man: Men’s fashion is all about the hidden details. Check your shirt for little added bonuses, like contrast fabrics, embroideries, cool labels, nice buttons, or $20 bills in the front pocket.

* Fit, fit, fit. All the tips in the world can’t substitute the feeling of a shirt that actually FITS. Avoid the baggy shirt or the pregnant man look. Too many off-the-rack dress shirts are made for the largest common denominator, meaning you’ll end up with a shirt that’s much too billowy and large to adhere to today’s “skinny-is-better” trend.

So next time you are in the market for a quality cotton dress shirt (why not today), do yourself a favor and go for a custom dress shirt.

It’s what all the cool kids are doing.

Welcome to the 21st Century: Pleats are dead.

image from http://permanentstyle.blogspot.com

OK, they’re not a complete fashion no-no like boxy jackets or white socks with black shoes, and we’ll even admit that we’ve seen them on the runway recently, but in our fashion eyes, a flat front pair of pants is far superior to pleated pants, especially when going the non-suit route. Dress shirts are becoming more and more tailored and fitted, and pants should follow suit (pun intended).

It’s time to face the facts. It just doesn’t look right to have a sleek, fitted button-up shirt tucked into a pair of pleated pants with all that extra fabric around the front. We’re not endorsing skinny, flat front dress pants for all—although, if you can pull them off, we heartily encourage you to—but, the message to take home is, wear pants that fit and say buh-bye to the boxy pleats.

Why? Well, it is just a fact that the majority of looking good is about wearing clothing that flatters your body. If your pants puff up in the hip area it makes you look full or bulky. If you are a skinny man, this just looks ridiculous, and if you are a larger man, it emphasizes an area you probably don’t want to emphasize. And since pleats (no longer) serve any functional purpose, we recommend you drop them off at the nearest Goodwill. Stat.

Once you’ve ditched the pleats, you can trade up for something better—like color and patterns! Just remember, if the pants are going to be somewhat loud, make sure you temper that with a more classic shirt, like this pink twill dress shirt.

So go forth and live your post-pleat life to the fullest.

And, in case you were wondering, we support anti-pleat evangelism. 

White dress shirts: suit-staple, yes; fail-safe, definitely; traditional, often; boring…

Not necessarily.

This may come as a surprise to many of you, but white dress shirts can do more than complete a great looking suit. They are often be used as a starting point, or a building block for trendy outfits.

To illustrate this point, check out one of our favorite white dress shirts that includes a spread collar (we hold it down for the spread collar) and French cuffs and imagine pairing that with a light, cool blazer, skinny tie, pocket square and slim jeans.

Imagination failing you? Check out this dude below. Now there is a coolness to aspire to. 

Image from the Sartorialist

And if you prefer a more edgy number, try a colorful cardigan or vest and a complementary tie. The great part about a white dress shirt is that it serves as a solid base when the rest of your outfit is going to be loud.

The basic message here is two fold. Choose a white shirt with a bit of character and then pair with some pieces (bright ties, pocket squares, cardigan, sweater, blazer, etc.) that will really shine in front of/on top of a white shirt. Just be sure not to commit the worst of all white dress shirt sins.

...looking like a waiter.

If you’ve ever worked in a start-up, you might be familiar with that one guy who wears running shoes, high-water jeans and a Hawaiian shirt to work. Here’s a pointer. Don’t be him!

image courtesy of santamariasun.com

At indiTailored we advise you to always look ridiculously good—wherever you work—and we’ve got a few ways to help you get there.

To start off, you should always look put-together. We’re not saying you have to wear a suit, but even at a start-up (one of the most laid-back working environments), everyone appreciates a tailored shirt with a pair of crisp trousers. It’s a simple look, but a winning one.

The key here is ensuring that your put-together outfit doesn’t end up looking boring, old, or cliche.

If you’re wondering how, we recommend experimenting with different collars, cuffs, and details. These little things keep the outfit looking professional and fresh, in addition to showing off your impeccable style and taste.

Case and point: Take the wide spread collar we recently wrote about. The wide spread collar on a slimmer shirt makes for a great Euro look—a far cry from what your father used to wear (thank god!), but still appropriate for the office setting.

And perhaps most importantly, don’t forget to play around with color! The black suit/white dress shirt/black tie will always make you look sharp, but color gets you noticed. Integrate salmon stripes or blue pin dots, find ties that complement your tailored shirts and trousers, and you’ll be well on your way to best dress in your office superlatives.

Don’t know where to start? Here’s an idea—click this link and start building your custom dress shirt!