Full disclosure: I am not an early adopter when it comes to shopping trends. I’ve been purchasing suits and dress shirts for twenty-five years, and over that time I have developed some deeply ingrained notions about how I prefer to buy clothes. Drive to the store, try it on, decide.
High-tech? No. Efficient?
Sometimes not. But it worked for me.
Until it didn’t.
Here’s the thing. When you’ve been buying and wearing tailored clothing for twenty-five years, you become…..paranoid about fit. Have you ever ordered an item of clothing that online listings said would fit you only to discover it was made in a dimensionally challenged warehouse basement?
I have. “Size 42 regular” that fit like a barrel? Check. Dress shirts with sleeves that were both too long and too short?
Yup. Five years ago I ordered a “classic American cut” sport coat from an online retailer. When it arrived it looked like it was tailored for someone with an NFL lineman’s waist but nothin’ up top.
For reals. It was un-wearable. Long story short, I refused to purchase another suit online until…well,until I saw Robert.
See, men’s clothing stores these days are few and far between unless you live in Manhattan or downtown Philadelphia. There’s lots to buy where I live…hoagies, car inspections, video gaming systems…but a nice selection of mens business casual attire? That means a forty-minute drive.
Two years ago I decided I needed some new basics…chinos, casual button downs, maybe a lightweight blazer I could wear in summer court. Margaret would say “just order them online” but I’d explain my fit frustrations and she’d sigh that sigh that wives sigh when their husbands are being ridiculous. I tried once.
It did not go well. One day I was having lunch with my friend Robert (works in finance, also wears a sport coat, and we have roughly the same body-type) and casually mentioned this dilemma. He looked at me like I’d just told him I was still using a Motorola Razr phone. “Dude,” he said, “don’t you know about Amazon’s try before you buy program?” Robert said. “I haven’t paid for clothes upfront in two years.” Look, I’ll cop to judging this gig from the get-go.
Amazon sells books. They sell household supplies. They sell hard-to-find wooden shoe trees. (Why do they sell wooden shoe trees?) But clothes?
Call me old-fashioned, but in my mind quality menswear is crafted by small businesses and curated by professional shop owners and salesmen. Amazon is the…online Amazon. Robert patiently explained that you can choose up to six try-before-you-buy eligible items, and Amazon will deliver them to your house for a seven-day trial period.
If you don’t like anything, you send them all back free of charge. You only pay for the items you choose to keep. Robert broke it down step-by-step and answered every question I had about how it worked.
Best of all? His answers addressed every concern I had about giving it a shot. I placed my first order that day.
Amazon will only let you choose items that are Prime eligible AND marked as part of their Try Before You Buy program. That’s a lot of clothing! Yes, that means Amazon House Brands.
And yes, some of their brands are actually quite good. Chinos? They’ve got you covered.
Button downs? Yup. Guayaberas?
Surprisingly, they do. I ordered three sizes of the same pair of chinos. Not knowing what size would fit I wanted to try them all.
Two dress shirts. One chambray-blend button down shirt I didn’t need but was curious about. Six items, all sent to my house with no money down.
It arrived Tuesday. Here’s a tip: when you’re trying on clothes that you KNOW fit but haven’t paid for yet, there’s no pressure. I don’t feel like I have to make something work.
The medium pair of chinos were too tight through the thighs (“medium” these days apparently means “makes you look like you ready to run a marathon”). The large was too baggy. But the waist was perfect on the 33” pair.
Shirt number one? Heavyweight cotton. Construction looked good.
Fit great through the shoulders. Shirt two appeared to be a decent fit online but had to weird blazer-type cut when I tried it on. Returned.
Blazer? Pretty damned nice. Better than I expected.
Into my keep pile went 3 items, back into the shipping box went 3 with pre-paid label already attached. Dropped it off at UPS on my way to work Thursday. Spent maybe ten minutes of effort.
Got charged for the 3 items I kept on Friday. Seriously. No arguing about returns.
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No store credit instead of refunds. Nothing. My point is…I was hooked.
Hooked, yes…but judicious. Once I figured out how to best navigate Amazon’s Try Before You Buy process, I started seeing opportunities I’d previously overlooked. Styles I wanted to try but wasn’t willing to risk buying without seeing in person.
That different trouser break I liked the look of but wasn’t sure would work for my body type. That purple oxford I thought looked cool online but knew would never get worn in real life. If I didn’t love something in person I knew I could simply send it back free of charge.
My financial risk had been eliminated, so I was able to gamble on things I otherwise wouldn’t have. Below, some of the lessons I learned along the way. Lesson #1: Buy multiples when in doubt Put simply: bracket sizes on anything that matters.
Think you should be a medium? Order small, medium, and large. Sure it takes up half your allotment of six items, but why stress over losing a $60 pair of pants that doesn’t fit just because you were “sure” they’d be a medium?
Trust me. I’ve wasted way too much time agonizing over “what if I keep it and it sits in my closet because it’s too big?” when I could have just ordered two more sizes. Lesson #2: Pareto optimize your wardrobe ahead of time.
Instead of placing random orders all year long, I like to go through seasonal wardrobe audits every few months. What will I need for upcoming season? What do I have that needs replacing?
What holes are in my wardrobe that need filling? I’ll make a list of potential items, then pick six that compliment each other and keep my wardrobe Pareto efficient. This has worked far better for me than ordering random items with no regard for how they’ll fit into my current wardrobe.
Lesson #3: Don’t wait until day 1 to decide As soon as that box arrives, I set a reminder for Day-Five. That way I can wear pieces around for a few days with stuff I already own to see how they feel after the novelty wears off. Sometimes I fall in love with something the moment I try it on, but won’t wear it after realizing it doesn’t go with anything in my closet.
Lesson #4: Make yourself style three ways before you keep it. Okay, this may seem contradictory to what I just said above, but bear with me. Once I’ve worn something around for a few days with existing pieces in my wardrobe I force myself to create three unique outfits with each would-be keeper before deciding whether or not to keep it.
If I can’t style it three unique ways with things I already own, it doesn’t get kept. Simple as that. This rule alone has helped me eliminate numerous orphan purchases.
You know, when you buy that great-looking shirt but it never actually gets worn because it doesn’t match anything else you own? Now, before all you influencers and fashionistas jump all over this article I want to be clear about what this service is and what it isn’t. I will not be buying my next court suit from Amazon.
I will not be severing my relationship with my tailor. I am not trying to replace brick and mortar men’s shops I’ve spent decades building relationships with. And I’m definitely not using this service for investment pieces.
But for staples? Yep, it works great. Department store basics?
Try before you buy is a lifesaver. Hell, Amazon’s own house brands have come a long way in recent years. Their Goodthreads line makes perfectly acceptable chinos and casual button-ups at great prices.
Plus it finally solves my “access to major menswear retailers” issue. Northern Va. is not known for its menswear shoppingselection. Amazon’s Try Before You Buy program has saved me money too.
Don’t get me wrong. I’m still spending money on clothes. But far less gas and time wasted driving to and from stores.
But what I love most is my “mistake” rate has plummeted. I’m able to make decisions about what to keep and what to send back in my own environment with my own lighting with my own closet. Not under the sad fluorescent lights of a department store fitting room.
Plus I now find myself occasionally splurging on pieces I know I will love but know I can always return if need be. Case in point: I recently used Amazon’s program to cheaply test drive multiple sport coats I was considering buying from Blu-Custom Clothing. I knew exactly how each Jacket would fit thanks to previously purchased Blazer’s that already live in my closet.
Armed with that info I recently bought a Gregory Berman custom blazer that I know I will keep for years to come. Something I never would have done before trying Try Before You Buy. Anyway, if you’re thinking about giving Amazon’s Try Before You Buy program a shot here are a few final tips to think about before you start placing orders.
Rule yourself off mindlessly browsing and picking the first six items you “need”. Instead, keep a running list of items you need as they come up throughout the year. Once you have six or more things on your list, do your research, then place an order.
Read lots of reviews. Check multiple sites for fabric compositions. Look for photos from other customers if possible.
Plan your orders around when you’ll actually have time to do a proper try-on session. Don’t let that box show up the day before a hectic work week. You’ll rush decisions.
And when you do make those mistakes (we all do), be honest with yourself about fit and function.
Yes, you don’t have to pay upfront. But that defeats the whole point of having a seven day trial.
Ironically, Amazon’s Try Before You Buy program has also made me more willing to spend extra on individual items. When I can easily compare a $30 button down to a $60 button down in the comfort of my own home I can directly see quality differences. Sometimes the cheap shirt wins.
But more often than not I find myself keeping that more expensive item because I can see firsthand that the extra cost is worth it. Something impossible to gauge by reading reviews online and looking at photoshop perfected retailer product photos. TLDR: I was sweater-unfriendly Amazon stereotypewhite guy.
Then I learned how to use their Try Before You Buy program, and it changed my life. I’m still picky about where I spend my clothing dollars. But I’ve never had it so easy to find perfectly fitting clothes I actually love wearing.
