A: One time I was at a fancy restaurant in San Francisco.  It was the kind of place where you have to wear a jacket to get in, and if you show up without one, they give you one from their closet.  I sat down and looked at the menu, which was pretty much completely inaccessible to anyone who’s not a Michelin-rated chef.  Rather than try to decipher it, I asked the waiter as casually as I could, “So how is the steak?”

“Oh, it’s terrible,” he replied.

Now, he was being sarcastic, but I got the point: whatever I ordered, it was going to be great.

If you pick the right restaurant, you don’t have to know anything about food and can rest assured that you’ll get a good meal.  Likewise, if you pick the right tailor, you don’t need to know anything about clothes, and you can rest assured that you’ll get a great suit.

Sure, I could give you a long laundry list of things to look out for.  But if you’re going to the right place, I’m certain that the tailor will be doing these things anyways. My one piece of advice would be to know exactly what you want in terms of color, fabric, and style going in.  The best tailors don’t give their input; rather, they simply do what you want them to do.  Besides, the whole point of bespoke is to make a suit for exactly for you.

If you haven’t gone down the bespoke path before, you likely don’t have a good bespoke tailor you can trust.  So do your homework.  Search online for user reviews of tailors in your city.  The bigger the city you live in, the pickier you can be, of course.  When you find a tailor that gets consistently favorable reviews, go visit the tailor and ask to see his/her work.  See if the tailor will let you talk to some of his/her customers and ask them about their experience.

Also, a “huge premium” can actually be really huge when talking about bespoke.  The Kiton “K50,” aptly named because it takes approximately 50 hours to create, costs $30,000 to $50,000, and is made exclusively by Kiton’s chief tailor who personally measures and fits the client.  If you already knew this and still are willing to pay this kind of premium, try Wilkes Bashford in San Francisco, which measures bespoke Kiton, or Kiton in New York.  If you’re in London, check out Kilgour or any other fine tailor on Saville Row. 

Finally, keep in mind that a true bespoke suit isn’t created overnight.  A bespoke suit will take you a few visits to create.  And a good bespoke tailor will allow you to wear the suit, get it cleaned a few times, and then go back for more tailoring for a perfect fit.

Style Tip 1: For more information on the bespoke process, and what you should expect to do (roughly) with each visit, be sure to read this discussion from Ask Andy About Clothes.

Visual Texture: The tiny gingham pattern on the scarf provides visual texture without going overboard with pattern.

Standout Accessories: The gingham scarf and the wood watch serve as standout accessories that speak style louder than a flashy top or jacket.

A: First of all, your wife is right.  Even when she is wrong, she is right.

Secondly, in this case, she really is right.  Jeans and a well cut jacket looks awkward; it’s something about the formality of a well cut blazer and the casualness of jeans that causes this clash.  Just because every other guy wears a blazer and jeans doesn’t make it right.  You can do better.

If you can’t get the matching linen pants, that doesn’t mean you should wear jeans.  Instead, try some summer lightweight chinos in an olive or a light khaki color (more slate than beige khaki), as the gentleman shown above does (though don’t follow his lead on the sleeve length.  And, of course, you could try finding some blue pants.  I’ve said it before, but you will see men in Milan wearing blue pants in lieu of blue jeans.  Any of these colors would complement your shoes as well.  The trick is to get a pair with the right cut, so as to not make yourself look like you just finished 18 holes of golf.  Try looking into Mason’s or Save Khaki; they make slim-but-not-too slim trousers in fantastic colors. 

Style Tip?  People often say that certain colors never go well together.  Don’t listen to them.  Certain colors are hard to pull off together, but just about every color combination can be done.  Below, a couple of well-dressed gentlemen show how to do brown/black and brown/gray color combos the right way.

I was skeptical too when I read that little tidbit, but I’ve since been won over.  The workmanship is top notch and the price, especially for the quality, isn’t outrageous.  Pictures don’t do it justice, but we’ll try anyway; here are four pieces we love from the GQ/CFDA “ Best Designer in America” winner.

Where to Buy:  Online retailers include Hefjina, Steven Alan Annex, and Stuart & Wright. Boutiques include Hollander & Lexer and Odin (New York), Legion (Los Angeles), Mac (San Francisco), Relish (Washington D.C.), and select Bloomingdales.  Though Engineered Garments has been around since 2005, it is only now that the industry has started to take notice.  As time progresses, I’m confident that more stores will start carrying Engineered Garments.

A: You’re in luck–you don’t need to spend a lot in order to look more mature.  In fact, you can often replicate a designer look at generic prices.  To me, the spirit of “young but mature” rests in taking staples of a man’s wardrobe and putting a contemporary twist on them.  The most common outfit you will see that captures this spirit is the classic t-shirt under the blazer look.  You may also see some guys pushing up the sleeves on blazers.  As for your specific question…

Pants: Ditch the cargo pants.  Those bulky pockets are just a bit too high school.  Instead, try some well-cut khakis in a lighter color.  They’re worth the investment.  I would look into a designer called Save Khaki; I like their cut and casualness. If you’re in New York, you can go to their boutique; otherwise you can find them at online at Barney’s Co-op, Neiman Marcus or Bergdorf Goodman.  And if its prep you want, look no further than a pair of Nantucket Reds; these classics are the very definition of East coast prep.  You can also try Ralph Lauren or J. Crew, which always has some good chinos (and of course, their classic chambray shirt).  Or, if you want something new, you can explore Gant’s Rugger line.  And while we’re on the subject of pants, don’t be afraid to try jeans that aren’t blue.  Grey jeans look great.
   
Shorts: For those hot days, look into some clean cut Bermuda shorts; they’re like cargo pants without the bulky pockets.  Nantucket Reds can be pretty stylish, as seen on Michael Bastian (pictured top right). Also check out what Banana Republic has to offer.  Style tip?  Properly fitting shorts do not fall below the knee.

Tops: You can stick to polo shirts, but I have a feeling that if you look around, every 3rd guy will be sporting a polo.  How to differentiate yourself from these other guys?  Look for polos that deviate from the common styles and brands.  Try investing in some interesting buttondowns; they’ll come in handy for dates too.  Solids and stripes are always a safe bet, but if you feel like being bold, try some checks or plaid.  Whatever you do, leave the collar down; a polo with a popped color isn’t preppy, it’s pretentious.

Shoes: Don’t bash yourself too hard about wearing slip on Vans; they’re actually coming back in style.  Also, classics such as Jack Purcells probably won’t go out of style any time soon, so don’t worry about wearing sneakers every now and then.  You can find some alternatively preppy shoes without breaking the bank though: try some Sperry Top-Sider or L.L. Bean boat shoes.

Blazers/Suits: Also, now that you’re in college, it’s time to look into blazers and possibly a suit if you don’t have one.  You’ll definitely need a well-cut suit for your job interview, so it’s only a matter of time.  For about $500, you can get some pretty good suits at Banana Republic.

You could always try the plain t-shirt under the blazer (or layered tees), but you can take the outfit up a notch by layering a fitted polo shirt over a t-shirt.  Bonus points for a brightly colored tee–we love the splash of color this creates at the neckline. 

Horizontal stripe patterns have emerged as a fresh-looking casual trend for both men and women this Spring.  From Burberry to John Varvatos, from American Apparel to Built by Wendy, this trend has manifested itself everywhere from high end fashion houses (hello Michael Bastian and Junya Watanabe) to accessible, affordable chain stores.  Here are a few pieces that do the horizontal stripe pattern well: