Shop Like a Man: 5 Simple Steps to Make Buying Clothes Easier for Guys

A lot of men HATE shopping for clothes. And I don’t blame them.

As much as I like suiting up and looking dapper on occasion—or being mindful of my outfit on an average day—buying clothes is hardly at the top of my list of activities.

Here’s the truth about why clothes-shopping generally sucks for men:

Clothing stores are designed for women.

If I may generalize for a moment…Women enjoy the process of shopping—taking their time, looking at all the different possible options, and hunting for the best price. To them, it’s about the experience. It’s actually fun for them.

So, when you think about the typical clothing store, it reflects that: a sea of colors and sizes and choices. It’s overwhelm on purpose. Because apparently “chicks dig that.”

Women Have Been Doing it All Wrong

The problem is, women have gotten this whole shopping thing all wrong. Or maybe a better way to say it is: men have been following the wrong lead. All this time, we thought we hated shopping? No, we just hate shopping the way women do it.

They like the experience, the browsing, the price-comparing, the JOURNEY…(again, this is a generalization so don’t get your panties in a bunch just yet).

We men just want to get to the destination: grabbing some new clothes.

As quickly and as quietly as possible—like Navy Seals on a midnight stealth mission.

But all these times we’ve tried to go “shop for clothes,” what have we done? Just what our mothers (most likely) showed us: go to the store, look at what’s there, and see if anything looks good…or worth buying.

And how fun was it? Not fun at all.

Great News: The Right Way to Shop is Actually Easier for Guys

The irony of all ironies? According to most style experts, the RIGHT WAY to shop for clothes aligns way better with men’s preferences.

Style experts—and not just the men, women, too—say you should actually plan and execute your clothes shopping like a special forces tactical strike. (Ok, they don’t use those words exactly, but…).

The last thing experts would recommend doing is to go to a store and just “browse.”

The best way to shop involves being highly strategic, disciplined and focused about your plan of attack:

1. Have an idea of what your overall wardrobe should contain

This may be the hardest part initially. But you don’t need to fear the “W-word.”

When thinking about your wardrobe, a big factor to consider is your lifestyle—your environment, your job…What core clothing items do you need in order to look and feel great doing, well…what you usually do?

In general, for your base wardrobe items you want to think versatility so the items are as interchangeable as possible. To do this, you’re better off getting neutral colors—like black, gray, navy, and tan—as well as smaller, more muted patterns.

If you need more specific ideas about what to include in your wardrobe, blogs like Real Men Real Style, Dappered, Effortless Gent, and Style Girlfriend are great resources. I especially recommend reading about Effortless Gent’s lean wardrobe concept for thinking about the composition of your closet. You can also check out my style fundamentals course here.

2. Make a list of exactly what you’re shopping for

Gents, this right here is the key—and the fundamental step we most often miss.

As Megan Collins from Style Girlfriend told me in an interview, instead of going to the store shopping for “new clothes for Fall,” you should be going to the store knowing that you’re after: 2 pairs of khakis, 2 dress shirts, a sweater in a neutral color…SPECIFIC items!

If you’ve done item #1 above, this should be easy: you’re essentially doing a need-gap analysis. Say you needed 3 pairs of khakis in your wardrobe, but you had 1 already, that means you need 2 more, and so on. Boom. Easy.

3. AGBTYL: Always go back to your list

(ok, that acronym won’t win any medals, but…)

When you’re out on a shopping expedition it’s easy to get distracted by “field conditions”: Unexpected sales. Judgment-altering shopping fatigue. Spontaneous crazy ideas about colored turtlenecks or novelty patterns…You’ve got to stay strong, sir. And remember why you came here. Sticking to your list can be difficult, but maintaining discipline here will save you loads of wallet-ache and Crying-Game-shower-magnitude regret later.

Even better is to stick to your list and set a time-limit. You can even make it a game: can you get everything on your list in 45 minutes? …Without knocking over any innocent bystanders in the process? It sure is worth a try. Grab your list and set that stopwatch!

4. Only pull the trigger when it’s really right

Ok, if you’ve made it through your shopping trip this far and you’ve kept yourself focused on your list, congrats! Now, once you find an item that you’re searching for, make sure it’s truly worth buying. How do you judge?

First, when you try the item on, remember that FIT is king. I’ve written about this before and talked about it in a recent video of my experience with made-to-measure shirts.

Knowing your measurements helps—really truly knowing your sizes. If you haven’t had a professional measure you, you should do that. But since measurements vary slightly between brands, what happens in the fitting room is key.

However, your understanding of fit is probably even more important. Most guys are content to go through life wearing clothes that are way too baggy. Don’t do that. As you try the item on, ask yourself: “Is there room for more than just me in this?” If you can comfortably hide a pineapple or a six-pack of Rolling Rock in your dress shirt, then MAYBE it’s too big. Just sayin.’

Love it in the store: If you’re on the fence when you’re in the store, it’s doubtful you’ll love it more once you get it back home. More and more, with clothes shopping and pretty much everything else in life, I’ve grown fond of the “Hell yes” test. When you’re trying to figure out whether you like something, if your answer isn’t a resounding “Hell yes!” then drop it and walk away. You’ll find it simplifies your decision-making greatly.

5. Embrace the ease and convenience of online shopping

Online shopping is like the “easy button” for man-friendly shopping. I’m not going to say that online shopping was designed for men. But if you’re a guy who always hated traditional clothes shopping and hasn’t given online shopping a shot, you’ll be in for a pleasant surprise.

It’s the most “un-shopping” way to shop. No visual clutter (you can often sort by your size), no stanky perfume counter to walk by, no other shoppers bumping into you, no sales people hounding you…and you can sit in your favorite chair (sans pants, if you like), sipping your favorite cocktail the entire time!

You still need to maintain the same discipline we talked about earlier: know what you’re looking for and stick to a shopping list, so you don’t get carried away… 

But to truly make online shopping work for you, the key is to quickly get comfortable with the logistics of ordering and returning items. Let’s face it, the big disadvantage of online shopping is that you can’t try the item on before buying it. Hell, you may not even know what the real color or fabric looks like—let alone how it fits—until you get it out of the package at home. The good news is that nearly all online retailers have very forgiving return policies.

My advice: order some stuff online and PLAN to return at least one item. This will help you get over that initial barrier of figuring out how you need to package return items for the retailer, along with knowing where your nearest UPS or FedEx drop off location is.

As Brock from The Modest Man says, the key is getting accustomed to the “rhythm” of buying online and returning things that don’t work. Once you do, there’s no going back….

Conclusion: Clothes-Shopping Ain’t Half That Bad

See? All this time, you thought the shopping experience had to be traumatic or painful…

Turns out buying clothes isn’t so bad after all. You just had to unlearn what you thought you knew about shopping.

Try out the tips above and see if they help improve your experience. Leave a comment below and let me know how it goes!