WALL STREET JOURNAL | JACOB GALLAGHER

BACK IN THE 1970s, if a man wanted a new topcoat, he had but one road to take: a visit to his local department store—or maybe a menswear shop named “Tip Top Tailors” or “Eddie’s.” Now consider the many paths that John Jannuzzi, 30, the U.S. deputy lead at Twitter Moments, will be taking to find a fall coat he considers a kindred spirit: He’ll scroll the pages of e-commerce sites like Mr Porter and Matches Fashion, weave through the racks at New York shops such as Barneys and Totokaelo, and check out popular resale website Grailed. “I’m into the experience of saying ‘I need a coat’ and then searching endlessly until I find the exact right thing,” said Mr. Jannuzzi.

Forty years ago, this infinite sartorial quest would have been unheard of. But today’s environment is much more conducive to shopping overachievement; the various ways you can buy menswear have multiplied like fine angora bunnies.

Now, you’ll find direct-to-consumer brands with shoppable social media feeds as well as physical “showrooms.” E-tailers range from monoliths with offerings as boggling as department stores to tiny, sharply curated virtual boutiques. The made-to-measure route offers both traditional tailoring and custom-fit casual wear. And don’t forget the burgeoning resale market which can net you deals on everything from gently used sneakers to Swiss watches.

Overwhelming? Absolutely. And perhaps that’s why some men aren’t tempted to venture down new retail avenues. “There are more options, but I think that for men, one of their basic requirements has always been shopping with efficiency and speed,” said Robert Burke, CEO and founder of retail consulting firm Robert Burke Associates.

You may be asking, if my shopping routine works for me, why should I give it another thought? Well, there’s always a better way to do everything in life, and that includes buying clothes.

The fact is, you’re probably missing a lot of what’s out there—which could in turn make you a better-dressed man. Even if you’re shopping online, you might not be clicking on the “Just In” or “Latest” tab on e-commerce sites like Matches Fashion and East Dane, which can give you a snapshot of what’s available for the season, week by week, including pieces you might not have searched for otherwise.

Finding a single store or e-commerce site that works for you can make your life easier, but limiting yourself to just one retail resource narrows your scope. That means not taking advantage of, say, the smart mix of Japanese, Italian and American labels at a boutique like Magasin in Los Angeles or the unique woodsy-cool selection of a shop like Askov Finlayson in Minneapolis.

Pounding the virtual pavement a little can also help price-conscious shoppers, who are well served by the increasing number of direct-to-consumer brands, such as Greats (sneakers) or Everlane (clothes and accessories), which offer quality merchandise with easier-to-swallow price tags since they’ve cut out the wholesale middleman. You won’t see their wares in any store—only on their own websites and social media feeds.

You can also stretch your fashion dollar by tapping into the many luxury resale sites like Grailed, an expansive secondhand site populated with fashion-forward merch, and the RealReal, a similar proposition. Charlotte, N.C.-based tech executive Dave Carr recently found an Engineered Garments jacket on Grailed for $225, about $355 less than its original retail price. If you open your shopping mind wide enough to consider (yes) made-to-measure clothes, you’ll find they can be surprisingly economical, too—and deliver a better fit than off-the-rack pieces tweaked through secondary tailoring. Providence, R.I.-based lawyer Vincent Ragosta (see his shopping strategies below) recently became a convert to the modern, made-to-measure New York-based brand Stòffa, whose clothes can be ordered via appointment or at one of its frequent trunk shows.

Another old-school route to reconsider: the personal shopper. You may think it takes a 10-digit bank account to afford such amenities, but stores like Barneys offer gratis personal shoppers who can decode what “smarter casual” means or do a closet overhaul. You can make an appointment online—and while shoppers do work on commission, they’re often more concerned with building a relationship than pressuring you to buy. For more guidance on how to navigate this multifaceted retail world, heed the advice of our three exemplary shoppers below.

THREAD COACHES // Smart Shoppers Share Their Best Retail Plays

THE SAVVY OBSESSIVE

Dave Carr, 41

VP Sales and Marketing, Levvel Inc.Charlotte, N.C.

The tech exec is a modern shopping savant, scouring the internet to unearth great finds and deals.

Identify like-minded stores I find new stores by going to the websites of brands I like and looking at the stockists [list of retailers that carry the brand]. I was searching for Thom Browne in Los Angeles and I found the store Union (pictured below). That’s also how I discovered Odin in New York.

Be social I use social media to find hard-to-get items. Last year, I really wanted Common Projects’ Chelsea boots. Need Supply Co. [a store in Richmond, Va.] posted on Instagram (pictured at left) when they got them in, and I bought them on my phone. I also use Instagram to find inspiration. What influences me mostly is independent boutiques. One I’m following lately is e-commerce shop No Man Walks Alone.

Make time for vintage I almost always buy preowned watches. The majority I’ve traded for watches I own. I don’t need more than three; I’m not a pro athlete. Most of my watches I’ve purchased online. Sites like TimeZone and Watchnet have forums and the resellers on them have been vetted by the community.

Invest wisely In the last few years, I’ve focused on my Holy Grail pieces—timeless things I’ll wear for years. I bought a cashmere Boglioli sportcoat (pictured at left, $1,995, Boglioli, 646-870-8250). It’s perfect. Compared with a Hugo Boss jacket you buy at Macy’s , which is going to look bad in two years, the Boglioli has a much better cost-per-wear ratio.

THE NO-NONSENSE ROAD WARRIOR

Russell Kelly, 42

Brand Manager, Tudor Watch, New York, N.Y.

The frequent flier knows how to spot the right shops for picking up a sartorial souvenir.

Loyalty equals efficiency For suiting, I have my go-tos, like Sid Mashburn in Atlanta and Freemans Sporting Club in New York. They have my measurements on file, so I can pick seasonal fabrics (Freemans swatches, pictured below left) when I’m in the store, or someone will send pictures. That allows me to easily do all my shopping for suits and shirts for the year.

Click with bricks Even if I’ve bought everything I want from a store via its website, when I’m traveling I like to visit just to check the vibe. Askov Finlayson (pictured below) in Minneapolis is one store I love going into. It’s really cool to see their perspective. At stores like RTH or Magasin in Los Angeles, you’re going to see exciting designers that you don’t get a full glimpse of online. Also, it’s better to see the colors of a fabric in person.

Size matters Online stores usually reference the size of the model wearing the clothes, i.e., he’s 5’10,’’ 165 pounds and wearing a medium. That’s helpful to get an idea of what something is going to look like on you. Even if you know your measurements, the manufacturers could have taken theirs differently.

Think global, shop local I really like Japanese brands such as Engineered Garments, Camoshita (pictured below) and Beams Plus. The aesthetic is casual but still put-together. I can find them at stores like Unionmade and Mr Porter.

Know when to take a risk High-end tailoring isn’t the best for experimentation. If you’re going spend that type of money, make a plain blue blazer first. To experiment, go with a shop like Freemans that has a more affordable bespoke program.

THE MADE-TO-MEASURE MAVEN

Vincent Ragosta, 61

Attorney, Providence, R.I.

The rakish litigator has a taste for fine clothing that extends beyond courtroom attire to custom suede jackets.

It’s never too late to change your habits I’ve recently given up the traditional route of going into a retail store and engaging in the quest for a properly fitting product. I used to drive into Boston to go to Barneys or Neiman Marcus. Although they have good offerings, you’re contending with finding the right salesperson to give you the attention you deserve. Sometimes you’d be competing with other customers and then the tailoring would be a gamble. When I discovered [New York-based made-to-measure brand] Stòffa earlier this year, I loved the concept. This year, I also purchased a custom suit by tailor Orazio Luciano (pictured at work, below) at the Armoury.

Custom isn’t always costly l feel I’m getting a lot of bang for my buck with my custom clothes. Stòffa’s hands-on service is special and the trousers and suede jackets (pictured at left, MTM 002 Flight Jacket, $1,500, stoffa.co) are spectacular. Stòffa’s trousers are in the range of $275 to $375, depending on fabric. The prices for high-end, off-the-rack trousers are comparable or higher, and then there’s the sometimes difficult process of alterations.

Get schooled When professionals educate you about construction and fit, and you’re enlightened as to the options, it makes a shopping experience more pleasurable. And it makes you appreciate the value of the final product.

Don’t rule out online I rarely purchase clothing online but if I need some sportswear, I’m not going to fight the crowds at Dick’s or Modell’s. I’ve bought good quality Bogner ski clothing from a small internet retailer. With items like that, I know what my size is.