Why Men's Clothing Subscription Boxes Suck


Listen to the Podcast version here.


Subscription boxes. I see why they’re a popular option. As guys, we enjoy things hassle-free. It’s part of the reason we don’t like shopping. If you don’t know what you’re looking for, you’ll spend hours running around questioning what you should actually buy. So what can you do?

Enter the subscription box. In theory, it seems to be a great solution. Most guys are trying to make things easy and don’t want to spend time concerned with clothing. This magical box comes along and tells you that it’s going to pick out your clothing and ship it to your doorstep. All you have to do is pay for everything monthly. No need to worry about what looks good, the box will tell you.

But then the box arrives. You open it expecting your style problems to be solved, but instead, it’s filled with clothing that you don’t really like, that sort of fits, and sort of feels like it will hold up, but you’re underwhelmed, to say the least. After trying everything on, you’ll now have to send everything back. Maybe you keep an item or two to justify things. This continues for months. After a while you have a closet full of things that are just “meh”.

I’m all for innovation - that’s what I started with this business. However, I hold that clothing and personal style should be learned rather than outsourced. Like changing a tire, knowing how to order off a wine list, shaving, and remembering to wash behind your ears, you should know how to dress yourself.

Learning to dress well is one of those things that will serve you well for the rest of your life, choosing pieces that actually suit you rather than having more and more clothing sent to your door every month that only kind of works.

When pressed to work outside the box, you’ll come up short. Special events, creative dates, formal attire, etc. you will have no idea what works for you - It wasn’t in the box that month.

I’m passionate about this because most of my clients come to me AFTER using these things. Which, unfortunately, means that they’ve wasted a lot of time and money and are going to have to invest further to do it right.

I want to give you some things to consider if you're thinking about outsourcing your style to one of these box companies. Let's dive in...


Undertrained Stylists

There doesn’t seem to be much of a requirement to work as a stylist for these box companies. They do usually give some training during their onboarding process, but it's minimal. Most personal stylists like myself have been in the game for years, doing a mix of different styling (online, in-person, editorial, etc.).

Most of us have also had extensive training, either working under someone or gaining certification. We work for ourselves. We need to be at that high of a level because our business depends on it. The employees of these box companies likely have no prior styling experience. Why would they? If they were that skilled with experience, they would be working for themselves or apprenticing under a more senior stylist. There’s also little incentive for employees of these box companies to spend a lot of time working on finding you the perfect purchases. They aren’t paid very well to begin with. Thrown in the fact that you can just send back the stuff you don’t like and if they make a mistake, their reputation won’t be harmed.

You Spend too Much

Each month you’re either paying for the subscription, paying for clothing, or paying for the “styling fee”. That’s a lot to deal with monthly. Clothing is not like food. Your closet shouldn't be a revolving door of menswear. You should be able to buy something of quality and have it last you a very long time. If something works well for you, why get rid of it?

The objective of all shopping should be to buy the best you can afford that works for your personal style, body, and color. If you do this, there’s no reason to fork over cash month after month for clothing you probably won't wear anyway.

Your Hands are Tied

Do you ever remember seeing an item of clothing that you absolutely loved? Think about it. It could have been a watch, a pair of shoes, a t-shirt. Whatever. You had to have it.

Now imagine not being able to.

Subscription boxes only send stuff from the brands they work with, which is sometimes, not many. It’s no wonder the guys who use these boxes all look the same. They were all sent the same stuff.

When I work with a client, or you shop on your own, the entire world is your store. I’ve recommended high-quality jewelry from a small shop in Brooklyn, leather jackets from an Australian motorcycle brand, and even saved guys money by telling them inexpensive brands where they can get basics. Whatever works best for the client.

You’d never get that from a subscription box. Even if they knew the brands, and put the time into figuring out what items would be perfect for you, they wouldn’t be able to give them to you. They are only allowed to work in the scope of what the box offers, which leads to generic choices.

Lack of Personal Style

So we have undertrained stylists with a lot of boxes to fill with a limited selection of clothing. You can use your imagination on the logical explanation of why these guys all look the same. The thing about personal style is that it’s just that. Even I can’t give that to you. It’s inherent. People can point you in the right direction and help you workshop it, but it grows and evolves, as you do as a person.

This is why you should take this into you own hands. If you learn to shop and what looks best on you, you can piece it together. You can’t rely on an algorithm or call center stylist to sort out what you need and expect to retain a sense of personal style.

No Useful Education

One of the best parts of working with a stylist or learning this stuff yourself is that you understand what works for you, forever. You understand why we dress your body this way. You learn why these colors work for you as opposed to those. You know how to shop efficiently and where. You develop a sense of taste and personal style. You see how to put outfits together and why some things pair well and others don’t. This is an education that will serve you well for a lifetime. Anytime you need clothing for any reason, you’ll quickly be able to confidently purchase it, knowing that it works for you.

Let’s take another popular subscription service - meal delivery. I understand the appeal, and for some it makes sense. But getting your food in a box, pre-portioned and sometimes half-cooked won’t make you a good chef. If you really want to handle this stuff, educate yourself.

Unfinished Touches

It doesn’t cover frames, hairstyle, skincare, facial hair, etc. If your grooming isn’t on point, the clothing won’t be of much help. You should be working to create the ideal image for yourself from head to toe.

They’re Lame

There’s no way around it, letting someone package the way you present to the world is not cool, in my opinion. There’s something magical about great clothing items. The way you come about them. The way you decide on them and against others. The way you can feel good about putting together and outfit that you picked and put together. Real style doesn’t come in a box. You can’t sell it. By going down the box path you’ve only put a bandaid over the real issue - you don’t know how to get dressed.

I’m all for innovation, but subscription boxes come up short in the long run. Based on what I know from previous clients, subscription boxes become pandora's boxes. If you really can’t take time out of your schedule to shop for yourself, go for it. But you know deep down that you want to know this stuff for yourself. You don’t want to be kept in the dark about what works for you. You don’t need a box filled with fabric, you need a brain filled with knowledge. Gain the direction you need, and take care of it. It’s so much easier than it seems. Think outside the box.

If you want more help gaining that direction, you’re in the right place. I work with you to cover your appearance from head to toe, showing you what works for you and why. If you’re ready to confidently handle your style and grooming, the first step is the free image assessment. You get advice directly from me about how you can make some easy changes to your appearance. Really, it’s free.