Trunk Club & The Case for Convenience Over Price

Full disclosure: This post is not sponsored/promoted by Trunk Club in any way. However, links to their site do contain a referral code. If you click on these links and sign up, you will be referred to my stylist and I will receive a $50 credit when you spend $50 or more. If you’re interested in signing up but do not want to participate in that referral program, I still recommend you work with my stylist. You can just that by visiting this link.


There are a lot of reviews out there for Trunk Club, along with virtually every clothing subscription service out there. Believe me, I read a lot of them before deciding to sign up. The big trouble I’ve had, which I’m attempting to improve upon here, is two things. One, every review I found involved the reviewer not continuing with the service or even keeping one item. Not out of dissatisfaction necessarily, but because they just wanted to write a review. Two, many are written by fashion bloggers. In my case, I needed help with fashion and happen to be a blogger, but this lengthy post was something I decided to do after signing up, not as the impetus to signing up.

So that is how I got here. Like many people, even a basic sense of style alludes me. Sure, there are countless articles out there that explain how to assess your wardrobe or give tips on where to improve. There are fantastic Instagram accounts that document the major and fringe trends in male fashion. There are even personal stylists available at the higher end department stores to take care of everything for you. I’ve dabbled with everything, but have always given up before really even getting started.

I’ve heard most men dress the way they did at 18 for the rest of their lives. Something about that point being a peak in masculine development, and there may even be chemical reasons why men are less apt to pursue an evolution in their outward appearance beyond that point. That may be an outdated mantra at this point, or at least there are far more men under 30 (and definitely under 25) that continue to adjust their style as they age. But if you go to Anytown, USA and take a look around, I’d say that holds true for a large percentage of the men you’ll see. That’s been my problem, and it’s made worse by the fact that I still dressed like an absolute bum at 18. So the outdated comfort zone I’m staying in was never a good place to be in the first place. It’s to the point that I’m not afraid of change, I just am simply overwhelmed by all of the options.

That’s where Trunk Club came in for me. I don’t know exactly what did it for me, but there was a point recently where I actually noticed everyone around me and how much more interesting, or at least less sloppy, their outfits were. Most of the people in my social/business circles wear decent-fitting button down shirts, nicer denim, basic stuff. But it’s clear they put thought and care into their dress. Meanwhile I’m in jeans that are just loose enough to not look good, basic t-shirts and oversized hoodies. For whatever reason, I noticed this and decided I really wanted to improve. I consider myself fairly creative, intelligent and at least mildly interesting as a person but my outward appearance usually presents me as a booger. Seems I’ve been doing myself a disservice. Regardless, it appeared my frustration in this department found reason for hope once I realized some of these clothing services online don’t just send you a box of whatever they want, but some actually have a person to help tailor it to you (no pun intended).

This grabbed my attention. Yes, I could drive over to Nordstrom and enlist one of their personal shoppers to do the same thing. It may even cost me less money in the end. But it will definitely cost more in terms of time. And irrespective of putting a dollar amount on my time (which, I should add, is often top of mind when you’re a freelancer…), I just would much rather spend my precious free time doing something other than hanging out at a mall. If I have a choice between a Netflix binge with my wife or fighting with people in a parking lot only to spend an hour or two wandering through clothing racks, the choice is simple.

That convenience of course, comes at a cost. You’ve certainly heard some variation of the expression “Pick two: cheap, fast, good.” (PS – I dislike that saying because it’s damn rare to get more than one of those options), well that applies here. You’re getting good clothes and a good service, it’s super convenient (fast), but means you won’t be bargain shopping. Their site claims “premium clothing”, so you must be prepared to pay full retail price.

All that said, let’s walk through my experience so far.

The Process & Basics

You can easily read on their website, but the very quick and dirty about Trunk Club is this… you fill out a simple profile on their site that gives indicators of your current style along with your clothing size.





They also ask you where you shop currently. If you fail to read through their FAQ, this may the first time you pause. Sure, there are some lower-priced retailers like H&M, but if you’re as inept as myself when it comes to fashion, you may pause here and wonder if this is the right service for you. (Granted, I do shop at some of these stores, but still manage to make poor decisions) I decided to carry on though.2016-01-07_12-21-27

The balance of the process is about sizing and personal information. It’s not all that interesting so I’ll leave it out.

My only concern was everything asked about how you dress today. Rightfully, it’s very generalized (e.g. casual vs bold vs dapper), it still was reflective of my current style, about which I was unhappy. I was hoping for something more aspirational, the, “how do you want to dress?” question. This made me wonder a bit if the service would actually help or if I was even the right customer. Maybe this was more for people who knew how to dress but simply didn’t have the time to shop for themselves?

I would just have to wait and see. I signed up over a holiday and went on with life for the day.

The Stylist

In my mind, this is the biggest differentiator between Trunk Club and the majority (maybe all?) of other clothing services online (I know Bomfell involves a stylist, but in all honesty it confused the hell out of me. Their How it Works” page says your orders are “fully personalized” and “handpicked” by your stylist, but immediately after they say there are “algorithmic recommendations” as well. I assume it’s a mix. It’s also not clear to what degree the stylist is involved in any consultation or general discussion). Many clothing clubs will cater to your style to some degree, some are focused on a particular style and pretty much everyone gets the same stuff, but in virtually every case it’s software doing the selection for whatever style and sizing attributes constitutes “you”.

In the case of Trunk Club, I got an automated email introducing me to my stylist almost immediately after I registered.


And by the time the weekend was over, I got an email directly from my stylist (minor note, I love this aspect. You can send messages through the website if you like, but I hate having to log into a site and use their messaging service over my own inbox) making a personal introduction, giving some preliminary information and inquiring about times for a phone call.

Right after the weekend ended, we were off and running. We chatted on the phone for maybe 30 minutes and it was a good start. Mackenzie was super personable and helpful. It was a conversation fairly evenly split between “getting to know you” and business, but the business end of it was definitely done with an informative/fun tone, no sales pitches. I didn’t notice during my signup process, but learned that the company is located in Chicago (I’m in Milwaukee, 1.5 hours away), so my stylist and I kinda knew some of the same people and had general midwesterner things to discuss. I also found out they offer in-person fittings at their office and apparently have your typical hip tech company space with a bar and whatnot. Next time I’m down there for work, I would definitely consider stopping in. That’s the same concept as the personal shopper at the mall, yes, but in a more enjoyable environment and with a person you have an existing relationship with, so it theoretically should be more enjoyable.

The important part, to me at least, is this initial conversation covered the aspirational bits I was concerned about during signup. I was able to try and articulate my concerns and recent revelation about how I dress, and Mackenzie asked about the typical environments I find myself in so an appropriate dress code could be established. This made me feel pretty happy about the whole thing, as at least it seemed whatever clothes I received would be based on what actually fits my lifestyle and needs, not some ultra generic descriptor like “business”.

We also talked about pricing, which I’ll get to below. But I wanted to point out that they are super up-front about this aspect, which is comforting.

After our call, I received a brief follow-up email from my stylist and within an hour I got an email that I could preview my first trunk online.

What’s in the Box???!!!???

To be honest, the speed in which that first box was assembled makes me question things a bit. I’m assuming my stylist was selecting a few things while we were on the phone. I also suspect that based on how you answer the initial signup questions, there’s probably some automated aspect that puts together suggestions the stylist can pick from. That’s totally my assumption though, no idea. But it was clear she listened. I mentioned having a hard time with fitting pants (I have wider hips, athletic-ish thighs – so no skinny jeans for me) and she included one style of pants in multiple sizes. Except for one bolder option, everything fit into my happy place of color choices. It pretty much looked like what I expected based on our conversation, which was great.

I didn’t grab any screenshots of the preview, but essentially their site had an image of each item, the brand/name, and a price. You could indicate on any of the items that you didn’t want it shipped to you at all (there’s no obligation to keep what is shipped, but this gives you a chance to catch any major disconnect between expectation and reality). I think I said no to two items. One was a shirt in a color I simply was not brave enough to consider. I forget what else, but it was something extremely similar to an item I have. There were other items that were similar to ones in my closet, but I wanted to try as much as possible at first to really get a feel for the service.

You’re given 48 hours to review your trunk and submit any feedback. I didn’t have any concerns, but I assume any major issues would delay shipment. In my case, I gave feedback in about a day and my trunk shipped almost immediately. And like I mentioned, I’m a short drive from their office, so it arrived super fast.

Here’s the fun part… this is what arrived:




Yay stuff!!!

The box included a letter / packing slip with a message from my stylist inside of a fairly nice envelope. It also came with a prepaid UPS return label and some pre-cut pieces of high strength tape to seal the trunk back up. What I didn’t expect, was some socks and boxers as well as a basic tee. Not a big deal and these simple cross-sell items help deliver a complete outfit.

Just as UPS delivered, that triggered an email from my stylist. She had a few comments about what to expect and some thoughts/opinions on why she picked certain items. It also had a handy collection of suggested outfits. Basically taking the individual item photos and pairing them together, but super helpful for me. Especially useful in realizing how to take the items I got and mix-match them in many different outfits (again, I’m clueless on this stuff). Here’s one example:


Pricing, Commitments, and What’s Next?

As I alluded above, pricing is a big deal for a lot of people. It seems to be the most common concern or question folks everywhere have about this service and others like it. Like I said, my stylist was very up front about the price ranges for their clothes and their general pricing model (you full retail price and that margin pays for the service). Their website outlines it too, but tucked away in the FAQ.

Our clothing is priced similar to high-end brands in department stores like Nordstrom. For example: Jeans are $170–$250 per pair, casual shirts are $100–$200 each, and sweaters are $100–$300 each.

Here’s one of the pages from the paperwork that came with my specific trunk, no ranges, real prices:


Now please allow me to dance around financial matters. First off, if my math is right, they sent me $2,036 worth of clothes for my first shipment. I have no idea if a shipment of this size is typical. For clothes on the casual end, I’d assume it might be a bit higher than normal. Since it was the first shipment, I know some size varieties were sent and that probably inflated things a tad.

Regardless, this is the point where you have to ask yourself, am I really going to spend $2,036 on clothes? Well, not at the moment… That’s part of how this whole thing works. I’m sure Trunk Club would love for you to keep everything. I’m fairly sure I saw an article saying their stylists are salaried (and when they started, they tried to do a lean model with no inventory and stylists on commission), but I’d still assume she gets some sort of bonus if customers keep a lot of this stuff. But you’re probably not going to keep everything.

In my case, some things didn’t fit. A couple things were really similar to items I already have as well. So I ended up sending over half of it back. But I did keep several things. For anyone who considers themselves frugal, the prices can be intimidating. Personally, I’d only ever spend money on suits and shoes, the rest was usually sale/clearance shopping. But I will do crap like drive two hours and pay $30/lb for coffee (it’s really good coffee though!), it’s just about how you value things. For clothes, it’s not about being able to afford them but instead about trying to consider what good clothing is worth for, really the first time ever. It’s like if your whole life you were eating $14 steaks at Applebees. Not because it’s cheap, but maybe because you live in a small town and there are no other restaurants that serve steak. Then one day somebody introduces you to a wagyu ribeye that’s been dry aged for 8 weeks. It’s over $100, but it’s an amazing steak. So the jump in price is scary, but if you can rationalize the jump in value, so be it.

Which leads to the next bit about commitments and whatnot. Everything is spelled out pretty clear on their website, but here’s the essentials…

  • They didn’t charge me until they received all the items I wasn’t keeping
  • There honestly was no pressure or incentive to keep anything at all, you could just send the whole thing back and either try again or quit and that’s fine
  • After your first order, there’s a survey to learn about your experience as well as to establish how you want to move forward. You can say you want stuff auto-shipped monthly/quarterly, whenever the stylist wants, whenever you ask, or not at all. There are questions about budget and types of clothes you want, etc.
  • Again, you can quit whenever. Obviously their goal is to do a good job and try to get you to keep as much stuff as possible, but there’s no hoops to jump through if you want to bail.

In my case, my current plan is to try quarterly shipments so as the seasons change I can keep improving my clothes. If I keep several items each time, I should be able to strike a balance of improving my wardrobe, hopefully being able to find similar clothes on my own to expand, while not investing an amount comparable to a 5-Series lease each year.

Back Up – What’s Full Retail?

This is fun, as I’ve seen a lot of people gripe about the “full retail price” bit. Several people make terrible comparisons saying you can buy similar items for way less, and like always, those people are dumb and missing the point. Others will say to wait for stuff to go on clearance, which kind of defeats the whole “fashion” angle. Really, the best route for buying nice clothes is to just buy things you like when you find them. But you can still obviously shop around, so let’s do that a bit. For any of these, I’m not hunting for hours to find the best deal, but am definitely digging through the first 1-2 pages of Google results.

Life After Denim Noho Shirt
Trunk Club: $118
From the Designer: $118
Elsewhere: $88.50 on sale (Denim Saloon)

Rodd & Gunn Benmore Sweatshirt
Trunk Club: $195
From the Designer: $195
Elsewhere: $195 (Zappos)

A.G. Graduate Navy
Trunk Club: $178
From the Designer: $178
Elsewhere: $178 (lots of stores)

Fidelity 5011
Trunk Club: $178
From the Designer: $178
Elsewhere: $176 (Zip Fit)

Of course, full retail is the same as MSRP, the price from the designer/manufacturer. But I included that anyway just to clarify there’s no additional markup. For these and a couple other products, I did find more impressive discounts elsewhere, but with big asterisks attached. Like, I found the shoes for half the price on one site, but it was a super discount store that only had two sizes available. That little sample makes Trunk Club look pretty good, though I’m sure when comparing more items, better deals can’t be had. But I suppose if you know what clothes you want and have the time to dedicate to deal hunting and waiting for sales, this service probably isn’t right for you.

Wrapping it Up

Alright, so in short what do I think? Well you can safely assume I’m happy with the service so far. Nothing at all suspicious or upsetting has happened yet, I believe my stylist is honestly trying to strike a balance between doing good for her company and doing good for me, and the products I’ve seen are really great.

Will you like Trunk Club? I think the biggest qualifier is that the benefit of having hand-selected and high quality clothing delivered to you has to outweigh the cost of paying full retail. If dropping $150 on a shirt is something you never would or even could do, then it’s an obvious no. If you believe people are suckers for paying full price for anything, same deal. Some people are fine with paying the prices and legitimately have no time to go shopping and especially don’t have time to keep up with trends (i.e. the typical overworked professionals like doctors, lawyers). Some people are fine with the price and willing to pay more for convenience and service. I fall into the latter group mostly. But obviously this is a fairly niche service, and you certainly need to make that decision going in. The good thing is, none of this comes as a surprise (not like that damn Columbia House membership I had in the 90’s… so many $25 copies of Genesis albums…)

One last thing, if you’re here because you’re considering signing up yourself, do my stylist a solid and give her some more business – sign up here.


Jay Ratkowski runs this joint, which is why his name is on the front door. You can find him elsewhere at Google+, Facebook, or Twitter

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Author: Jay

Jay Ratkowski runs this joint, which is why his name is on the front door. You can find him elsewhere at Google+, Facebook, or Twitter

2 thoughts on “Trunk Club & The Case for Convenience Over Price”

  1. Nice post. I really like that you are upfront about the referral. I find lots of bloggers are very shady about it. Refreshing! I personally love Trunk Club and have a different stylist than you–so I think there are lots of good ones out there.

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