The First Time Suit-Buyers Cheat Sheet

Suit, pocket square: J Crew Ludlow. Bag: Frye. Shoes: Cole Haan. Photo: © The Next Gentleman

When I was younger, I detested dressing in anything other than graphic tees and thick skateboarding shoes. (Talk about one of those, “What the hell was I thinking” phases.) But as time passed, I grew into myself and was able to develop my own personal image.

My wardrobe revelation really began when I had to start buying suits for work.

For many young guys, their first “real” suit is mandatory for job hunting. It’s an image thing — you now need to fool adults into thinking you’re a professional and not a college student. Hey, fake it ’til ya make it!

I don’t come from a suit-wearing family, so naturally my first time shopping for one was extremely confusing. I literally had no idea where to begin. Unfortunately, not knowing what to look for lead to costly mistakes, both financially and fashionably.

Since 2010, I’ve purchased about 17 suits. I’ve had all kinds of labels; Hugo Boss, Express, and John Varvatos to name a few. I wear less than half of them today on a regular basis. This might seem like a huge waste of time and money because, frankly, it is.

The question is “Why?” My body hasn’t changed in the last six years – but my understanding on how a suit should fit my body definitely has.

If there were three things I know today that I wish I knew back then, it’s the “what,” the “how” and the “where” of how to go about this venture.


Goofing around in an Express Photographer Slim Fit Suit. Photo: © The Next Gentleman
Goofing around in the Photographer Slim Fit Suit from Express. Shoes: Cole Haan. Photo: © The Next Gentleman

Dude, what kind of suit do you want? Two or three-piece? What color? Single or double-breasted?

Peak or notch lapels? Center or side vents? How about no vent?! Do you need it monogrammed incase you lose it, ya nitwit?

First, unless you work in a funeral home, a cosmetics department, or attend weddings for a living, you can plan on leaving the black suit on the rack. Trust me. As for the other specs, well, that’s up to you. But if you lose things frequently, I’d think about the monogram. Anyway…

My very first suit excursion was to K&G Fashion Superstore… “cuz they have suits and whatever.” I’ll never forget it, I couldn’t decide what to get and was actually late for my second day of work. I opted for both a black and a gray three-piece suit, each with peak lapels and side vents.

The gray suit was a total winner; neutral in color and pairs nicely with black shoes or any shade of brown. Gray also allows you to choose basically any color shirt/tie combination to wear. The black suit, on the other hand, was something I found to be way too formal for a work-type atmosphere, and didn’t end up wearing as much as I should have. #Lessonlearned.

Your first suit should be either a nice medium/dark gray or a sharp navy. For versatility purposes, the gray has a bit of an advantage over the navy. The gray suit option allows the shirt and tie, which are less expensive and more interchangeable, to easily act as the stars of the outfit. This helps keep your look fresh and new, and not like you’ve been wearing the same damn suit all week.

So now that we know you need a gray suit…


There are two “hows” you need to ask yourself when looking for your first suit.

Good looking friends are the best accessories. Photo: © The Next Gentleman
Suit: J Crew Ludlow. Tie: Original Penguin. Shoes: To Boot New York. Friend: Chelsea Marks. Photo: © The Next Gentleman

How do you want it to fit? The answer is based on your body type. I learned this by messing up and buying a bunch of suits that didn’t fit me properly. There are a few things you can do to avoid making that same mistake.

Get measured! Chest, waist, and inseam. Work with a knowledgeable sales associate. I’ve found older guys have sized me more generously than the younger guys have, and that’s the battle of the classic fit guys v. the modern, “slim” fit guys.

My first suits were very boxy and a whole size too big. My suits now are actually the right size and fit my body snug while maintaining comfort. I look back at photos of myself and see a flying squirrel because all the excess fabric around my slightly above average build.

Don’t fit the suit, make it fit you. Start by choosing the right fit for your body. “Classic,” and “Original,” like my first suit, are more full and slightly boxy. You’ll also find styles along the lines of “Tailored,” “Slim Fit,” and “Tapered,” which are all variations of the more shapely, contemporary look. Sleeves should end around where your hand begins. Make sure you’re happy with the drape, or the way the fabric hangs around your body, to get the shape you like. Most brand try to distinguish their contemporary fit by calling it something unique, so again, partner with a sales associate.

Also, when it comes to alterations, it pays to befriend a great tailor. These people are the all-knowing grease monkeys of clothing. They know the ins and outs and what random buttons were on Nana’s Levi’s back in ‘64. They’ll learn the way you like your garments to fit and can provide feedback on how the fabric will react and look on your body afterward.

How much is in your suit budget? Who’s the baller, you or Nana? It’s okay to have a limited budget, but at the same time, you’re going to get exactly what you pay for, quality-wise. If we know that this suit is going to be worn frequently, consider ramping up the investment for a durable suit that won’t unravel.

I advise many first-time buyers to be thinking about the $350-$600 range. Even if that sounds like a lot, remember, you’re going to be making money while wearing this suit, so it pretty much pays for itself.

Okay – now we know you need a gray suit and you have an idea of how you want it to fit…

Waiting to be sized for the length of the new pants. Photo: © The Next Gentleman
Waiting to have my pants marked up at J Crew. Photo: © The Next Gentleman


Where do I go? You go to the suit store!

First, know that there are a few different options available when it comes to looking for somewhere to buy:

  • Pre-tailored
  • Semi-tailored
  • Made-to-measure
  • Bespoke

All brands are going to fit you a little differently from each other, regardless of the way the model is described on the tag. Size is a guideline, not a law. This means that a J Crew 38R might fit you perfectly while a Topman 40R might fit similarly. Don’t get confused by this! Begin with the measurement, but listen to your body and be comfortable.

Things I look for when fitting myself in a new brand are how constricting the shoulders feel, if the the jacket is too tight across the sides and belly when buttoned, and how tight the pants are around the calves and in the crotch. These are pretty immediate indicators to whether or not the fit and/or size is going to work.

I stress the utilization of altering your garments, but some stores offer suits hot off the press, or “ready-to-wear,” like J Crew or Express, that fit pretty well. Some of my best suits are of this nature. Otherwise, majority of what you’ll find in stores like Nordstrom or Zara are suits off the rack that need minor alterations; a hem to take up the pants or maybe the midsection taken in a tad.

Other options are more of a customized look. Made-to-measure programs, found at most major department stores, incorporate the transformation of a suit from a base model to your measurements.

Bespoke, on the other hand, involves creating a complete, personal garment for your body only. One brand making waves in this fashion, no pun intended, is 9Tailors in Boston’s Leather District. (Definitely check this out. You won’t be sorry.) It’s just cool to know you own something nobody else has. It definitely has potential to up the compliments you get from people!

All the essentials to complete the outfit. Photo: © The Next Gentleman
Tie: John Varvatos. Pocket square & lapel pin: Hook & Albert. Photo: © The Next Gentleman

No suit is going to look complete without the proper accessories. Time for fun, snazzy ties, a pocket square, and a slim tie bar to cap it all off. A great one-stop-shop for these is The Tie Bar or Hook & Albert. I like to make sure my materials match. Cotton ties go with cotton pocket squares and silk with silk and the widest part of your tie should match the widest part of your lapel. Compliment the colors and the patterns you’re already wearing.

Bring your ideas to life and have fun trying different combinations; there isn’t one right answer. And definitely don’t feel compelled to shop in the same place your suit came from. I find many suit accessories through The Tie Bar, Nordstrom, and J Crew. You never know when you’re going to stumble upon something neat.

Basically, suits are awesome when they fit. You know you look good when it’s on, and it’s a special kind of good that makes you feel like a boss. Your look will get better with time and experience, so start today. In the words of Barney Stinson, “Suits are full of joy. They’re the sartorial equivalent of a baby’s smile.”

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