Ok gentlemen, this is it. The supreme enchilada, the party of all parties is finally just around the corner: New Year’s Eve.  And considering how crucial it is to look your finest on this particular evening, we’ve saved the New Year’s Eve holiday fashion tidbit for last.

Now whether you’ve realized yet (or not), you’ll have quite a lot to celebrate come December 31st. After all, not only is the whole year said and done, but you’ll have successfully made it through another holiday season with weird relatives and long-distance acquaintances who you’re afraid to be alone in the same room with.

And yes, we do admit that with New Year’s does come with social pressure to “do it up right,” but don’t let the hype intimidate. The key to the success is confidence. So guys, this means it’s time to put your best cuff forward and say, “goodbye 2009, helllllllllo 2010!” 

Clueless how to deal with all this fashion anxiety you didn’t even know you had? No worries, indiTailored’s got your back—literally.

For our “New Year’s Eve Party” shirt, we’ve chosen a bold purple and pink check look that’s sure to show off your confidence and kick the year off with a bang. Made from fine, 100% cotton straight outta Italy, this shirt is sure to make a statement on an evening that calls for just that.

And with purple contrast collars and cuffs, the three button barrel and a slick executive collar to finish the deal, this shirt comes well equipped with undeniable style and flare.

So cheers to you, my friend. With this shirt, 2010 is definitely lookin’ good…

After Santa comes, the feasting is over, and the extended family start to file out, the day after Christmas is suddenly a safe haven where you can breathe a sigh of relief because you’ve officially survived the holidays.

But listen gentleman, just because the big day is done, you don’t have permission to slip into your old college sweat suit. Like we talked about yesterday, your mom and even your girlfriend (if you were lucky enough to bring her home), still have to look at you.

That being said, although we still expect style when you get dressed post Christmas, we understand how crucial comfort is to you. After all, you have spent the past few weeks stressing to finish up work at the office, shop for holiday gifts, and deal with Aunt Betty who still likes to squeeze your cheeks.

The best part about indiTailored shirts is that we have looks for every occasion, including the days when you want to look good and still feel comfortable. So for our “Day After Christmas Shirt” we’ve chosen this casual, yet stylin’ bright blue/yellow striped shirt that strikes the perfect balance between too dressy and not dressy enough. This shirt screams “holiday appropriate” and lets your family and significant other know that although Christmas is over, you still care about putting yourself together.

If you decide to transition this shirt from daytime to night, pair it with a tie and blazer. Need to get some Grandma time in before you head back to your pad? Throw a cream colored sweater over this shirt and you’re guaranteed to look handsome, yet soo precious…

The holidays really are a magical time of year.

Skeptical? Okay—Well, when else can stout men put on bright red, jingle a couple of bells and poof—people appear less stressed, less frowny, and more inclined to say “please” and hold doors. It’s really quite astonishing.

But let us guess. It takes more than a jolly old plump man to lift your spirits…

Our suggestion? Start workin’ the boss today, cross those fingers real hard (you may need some serious luck for this one), and perhaps the holiday cheer will compel the big mucky-muck in your office to utter those words you’ve been dreaming about for weeks now…

“You know, [enter your name here]? You’ve worked hard enough this year. Don’t even bother coming in between Christmas and New Years. Enjoy the break! You’ve earned it!”

Regardless of how far fetched this scenario may seem (REALLY far-fetched), we at indiTailored encourage you to take time for a little excursion this holiday season, even if it is just a short jaunt—because we all know, the holidays are the time of year to be a tourist.

And whether you’re taking on the big city or exploring your quaint hometown, it’s advisible to embrace your inner tourist and travel in style.

So to be the most fashionable tourist on the block (not actually hard to do), we recommend this London-inspired red and black check shirt—complete with a double button spread collar and black and white contrast collar/cuffs, for a shirt full of character and dimension.

Now, off to finding that partner in crime for your winter wanderlust…

There is nothing wrong with being a momma’s boy. In fact, there’s a long list of things that are right with having a special soft spot in your heart for your mom. After all, she did carry you around for 9 months, pack your lunches before school, and buy you clothes until you (recently?) learned how to dress yourself.

That being said, with all the tender love and care your that your mother has given you over the years, it can only be expected that she’s overjoyed with excitement when you tell her you’ve booked your ticket and are heading home for the holidays. And even if going home means dealing with inevitable family stress and weird relatives, you know deep down that you, too, are looking forward to seeing the fam and being taken care of for a bit.

So we ask you please, do your mother a wee little favor, and take some time to put yourself together. Although she may not be that special lady you want to impress, odds are, she’s just as judgmental. So for her sake (and your sanity’s sake), please dress accordingly and assure the matriarch that you’re as handsome as she knows you are.

Our advice? Show your softer yet stylish side by wearing the color lavender with a complimentary brown/purple check contrast collar and cuff (fact: moms love their sons in pastels and appreciate little style details). A button-down collar and tailored fit will give your shirt a casual (but not unkempt) feel—the perfect look for your first day back—and will undoubtedly make your mom proud.

And if momma’s proud, momma’s more likely to feed you—and don’t try and fool us for a second. We know home cookin’ is one of the main reasons why you trekked home this season…

The holiday season may be a whirlwind, but you must remember to take a few moments this December to look longingly at that special someone in your life and get a little extra motivation to do something, well, special (believe us, you’ll never hear the end of it if you don’t…).

That’s why especially during the holidays, indiTailored puts our full stamp of approval on date night.

That’s right gentleman, it’s time to show your special lady friend how much you appreciate her—and if you’re going to put in a bit more effort to say, “I care,” you must do it with the proper style.

So for our “Date Night” shirt, to have you looking your best at times of crucial importance, we’ve selected a dark blue pinpoint shirt with a classy spread collar and a purple flowered pattern contrast.

With a shirt that shows sophistication, personality, and class, you’re bound to impress your gal with your sense of style. She’ll love that her man is comfortable enough to sport a floral contrast collar and cuffs and you’ll appreciate the feel of this 100% cotton, 80s 2-ply pinpoint.

Taking her out for something extra fancy (again, indiTailored fully supports such activities during the holidays)? Pair this shirt with a tie (full windsor knot, preferred) and simple silver tie bar. Add a sweater or fitted blazer to complete the look and you sir, are set for a magical evening.