A friend recently let me in on a style secret he’d been keeping. After a couple of drinks (for courage, of course), he leaned in and whispered, “Megan, I don’t know how to shop for clothes. When I go to the mall, I just walk into the store, check out the mannequins…and buy whatever they’re wearing.”

Sheepishly, he lowered his eyes and asked, “Is that cheating?”

Well, yes and no.

On the one hand, I totally understand that a lot of guys need help shopping for clothes but don’t necessarily want to ask for it!

When I worked at Abercrombie & Fitch a million years ago, we would receive huge binders twice a month from corporate headquarters. They were instructions on how to style the store, down to the exact angles of each t-shirt stack on a table. It took me a month just to master all the ways to fold a pair of jeans.

And the mannequins? Forget it. That was a manager’s job. With countless details to get just right, A&F HQ couldn’t afford to leave that task to anyone but a trained professional.

Knowing that every detail of a retail store’s look has been thought out by style experts can be helpful. It means if you “shop the mannequin,” you will walk out with an outfit that an expert put together. They just might not suit you, though.

So yes, this course of action takes the skill (and I would say, fun) out of building towards a personal style that’s truly unique to you. Though of course, there’s an argument to be made for cutting the guesswork out of stocking your closet.

Why figuring out how to shop for clothes can be so hard

In The Paradox of Choice (a book that explains literally everything about why we are the way we are…seriously, go read it), Barry Schwartz argues that eliminating options in consumer behavior can greatly reduce anxiety. Most people are one of two “types:” maximizers or satisficers.

Maximizers consider every alternative before making a choice.

Meaning, they might find a plaid flannel shirt that meets their criteria (price, color, fit) in the first store they look, but they’ll still stop into every other store at the mall to make sure there’s not an even more perfect plaid flannel out there.

Satisficers, on the other hand, make decisions aiming for a satisfactory or adequate result, rather than the optimal solution.

Meaning, they’ll buy that first flannel shirt as long as it meets their standards (which are generally the same as those of the maximizer), without worrying that there may be a better shirt still out there.

Schwartz argues in favor of a satisficer mindset, as maximizers tend to:

1. spend extra time shopping with the same results, and
2. feel less confident about their purchases.

Maximizers wind up with a perfectly good shirt, but constantly worry about the one that may have got away. Satisficers wind up with a perfectly good shirt, like it more, and worked to find it a whole lot less.

So Schwartz would most likely affirm my friend’s “shop the mannequin” strategy. He gets new clothes, and he doesn’t spend all day at the mall.

But!

There’s also drawbacks to this shopping strategy.

1. The clothes on the mannequins are almost certainly full price.

From Gap to Gucci, window displays are carefully selected to showcase the brand’s latest and greatest offerings. Though, Schwartz would argue (and I’m inclined to agree) that if paying full price beats worrying about if you’ve pulled together an acceptable lewk, then it’s worth the extra cost.

2. When you shop exclusively head-to-toe looks, you wind up looking like…well, the mannequin in the store window.

It doesn’t show much of a sense of personal style if you wear one brand head-to-toe. If anything, men often look less competent, stylistically speaking, when they dress exclusively from one store, or wear the same outfit over and over without getting creative and mixing in different pieces from different brands.

Not that there’s anything wrong with an assist! 

You’re reading this now because you recognize that having some help in the style department serves as both a time-saver and a reassurance that you’re walking out of the house looking right.

If you’re not really interested in flexing your personal style muscles, then walking up to a sales associate with your head held high, pointing at the mannequin and saying, “I’ll have what he’s having” might be perfectly adequate.

If, however, you want to dress better, and you want to gain confidence in your own taste and personal style, you’re going to have to give shopping more of a college try.

And I speak from experience! Despite what countless romantic comedy movie montages have led you to believe, not all women love a shopping spree set to a catchy Top 40 song. For me, it’s a challenge I have to psych myself up for, and I think most men approach the task the same way.

If you’re like me, you commit to your time shopping the same way you commit to an afternoon with your significant other’s grandparents. It won’t be fun, but you’re going to get through it.

Below, 8 tips on how to shop for clothes like you know what the f*ck you’re doing:

1. Prepare

What do you need? An all-new fall wardrobe, or just a few new sweaters? A suit? What color? Make as many decisions about what you intend to buy before you get to the store. Bring a list, and check things off as you find them.

2. Take your time

This may sound crazy, but if you’re able, I highly recommend taking a day off from work to do your seasonal shopping. Hitting up stores after work and on the weekends when you’re exhausted and stores are busier can discourage you from even trying anything on. If you can take even a couple hours to do some shopping on a Tuesday, you’ll get through your list more quickly and with less hassle.

3. Figure out how you shop best

I’ve never shopped well with others. I know what I like and don’t really want to drag someone on what are essentially errands. That’s not everyone’s M.O., though. If you want a second opinion and have a (really) patient wife, girlfriend, or fashion-inclined pal, by all means, bring them along.

Just know that you’ll tear through the mall faster without anyone else in tow.

4. Shop for the season

Try to tick as many items off your list as possible in one trip. Going out for a new tie here, or a replacement pair of jeans there eats away at your schedule, and you’ll probably spend as much time looking for one thing as you do for five.

5. Buy in bulk

When you find a staple item that fits just right, buy as many as you can afford. If, for instance, you wear chinos all the time, buy two pairs so you can wear one when the other’s in the wash.

If you want to buy the same thing in different colors, go for it; just be realistic about the shades you’ll really end up wearing.

6. Only buy what you love

This one should be a no-brainer, but if you find yourself reluctantly bringing an item up to the register just because you “need something like it,” don’t buy it. You won’t wear it, or if you do, you won’t feel very good about yourself in it. If necessary, wait a day to decide, then buy it online. Paying for shipping is worth the confidence you’ll have in making the purchase.

What about sales? We get asked a lot. Here’s our advice:

Buy it if…

You wonder why it’s on sale.

“This [coat/sweater/belt/etc] is great!” you think. “Why is this on clearance?” Maybe a shirt in your favorite color didn’t sell that well, or the shoes seem off-brand for the store where you found them but are totally your style. A good sale purchase is one you’d make even at full price.

For instance, last summer I fell in love with a pair of orange, (sort of) strange-looking tie-dyed wedges at DSW. I waited a week and when I went back to the store, they’d been marked 60% off. Turns out, no one but me wanted citrus-hued hippie heels. Fine by me! Find your orange tie-dye wedges (metaphorically speaking of course), and hand over your credit card with confidence.

It fits!

Relatively well, at least. If you’re considering a suit jacket or blazer, for instance, make sure it fits across the shoulders. If it doesn’t, you’re going to spend all the money you saved at the register on tailoring, and your new purchase still won’t look that great.

Cut to: you pulling it out of your closet once a month, remembering it doesn’t fit well, and stuffing it back inside. Your “steal” will never see the light of day.

Skip it if…

You’re making excuses.

“Well, okay, sure, the pants are pleated, but I mean, they’re half off!” Sorry, but if you don’t like pleated pants when they’re full price, what makes you think the money saved will magically turn you into a pleats lover? Don’t try to convince yourself an item is your style just because it’s suddenly in your impulse buy price range.

It receives a less-than-enthusiastic reaction from the crowd.

If the salesperson or your shopping companion says, “It’s…nice.” If she likes an item on you, she will say so. If she doesn’t, she’ll say, “It’s nice.”

7. Ask a salesperson

Okay, maybe not the Gap Girls. But otherwise, utilize these precious shopping resources! I’m the first to make a beeline for store employees, usually before they can even ask if I need any help, an offer usually turned down by shoppers with a quick, “No, just looking!” Exactly, you’re looking for clothes to buy, and the salesperson will be able to direct you to exactly what you’re looking for. On the other hand, if the store doesn’t sell what you want, you’ll know right away without hunting all over for it.

8. Treat Yo’Self

Searched through a stack of shirts twenty high and can’t find your size? Can’t fit in the same size pants you used to? Shopping is hard, and can make you feel pretty awful sometimes. When you’re feeling discouraged and want to just go home and watch trashy reality tv on your couch (or, okay, maybe sports, or whatever), treat yourself to an ice cream cone/Orange Julius/pretzel/[insert coveted random junky mall food here] at the food court. No, it’s not healthy, but whatever gets you back out for round two is worth it.

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Still feeling overwhelmed? SG can help

If you’re ready to invest in some new clothes but dread the thought of shopping for them…consider having Team SG shop for you! We’re obviously biased, but we swear it’s really great!

Let us rescue you from shopping fatigue and sartorial apathy. We can promise the kind of personal attention and care that will make you feel like the best version of the awesome guy you already are! If you’re ready for a style upgrade that’ll seriously improve your closet and your confidence, give us a shout.