In a perfect world, every business deal would close, every workout would yield visible results, and everything we wore would draw men’s respect and women’s phone numbers. But all those things take time and, in a perfect world, we’d have more of that, too.

Well, the folks at Trunk Club are taking us one step closer to ushering in this perfect world, at least when it comes to clothes.

Using a webcam to connect you with your own personal stylist, Trunk Club “Experts” create a shopping experience somewhere between online clicking and self-parking. I dove in head first with this too-good-to-be-true sounding service and learned that it might finally be time for us to change the way we shop. Seriously.

Attention Skeptics

I have to confess something upfront: I like clothes. A lot. I enjoy shopping for and reading about clothes both on the web and in magazines; I see what people are wearing and look for good deals and great fits. I don’t mind spending a few hours trying on different things to get exactly what I want.

Before you stop reading any of my articles, unfriend me on Facebook, or stop following me on Twitter, let me first assure you I also love fast fast cars and chopping down trees. All man here… I just happen to like cool shoes, too.

Let me first start by saying that I’m a bit skeptical when it comes to online shopping, particularly with clothes. Yes, there are merits, but often times there’s an experience lost somewhere in between entering my credit card information, clicking the mouse, and hearing the FedEx truck’s honk.

Trunk Club aims to never let that happen again.

Personalized, Expert-Guided Shopping Experience

I first began this clothing quest for convenience by signing up on their the Trunk Club site. Within 24 hours I was contacted by a style expert. She informed me that I needed to download Skype, so we could chat with our webcams (Don’t have one? Trunk Club will send you one for free.) at a date and time of my convenience.

So we met. My expert and I spent 20 minutes discussing everything from “what kind of pants do you currently own?” to “who are people whose style you like?” and so on. Other points of discussion include style needs, desire, likes (properly fitting jeans), and dislikes (cargo shorts).

She asked about a few pieces of clothes I really liked and I was able to show them to her live via webcam. She tracked with me, took notes and, in no time, had ideas for items to include in the “get to know you” box - a litmus test to track our style compatibility.

You keep what you like and send the rest back. Done.

The next morning, my “get to know you” box arrived, via free overnight shipping. I ripped it open to discover new brands, fits, colors, and styles that I might not have normally picked up. Think of it as a care package from your own personal stylist. I tried them all on (off camera, of course) and showed my expert. By this time, we had built a healthy rapport. She was able to be very blunt with me, something I need and appreciate. Some of the articles fit great, some didn’t fit at all. Some great, some not so great. However, the styles were overwhelmingly me. They were just on the edge of the stuff I currently wore. I was pushed just a tad and I looked great. We mutually decided I needed a size down in everything they had shipped me.

We set up a follow-up time, she e-mailed me the free shipping return label, and I sent back the clothes. A few days later, the items I liked arrived in the better fitting sizes and everything worked perfectly. My expert even included a few Ben Sherman shirts that weren’t even in stores yet. I kept what I wanted and got another shipping label to send back what I didn’t. That simple.

Who’s It For… You Might Be Surprised

Let’s talk brass tax, fellas. Trunk Club is a luxury service. Hand picked clothes, a personal stylist, and free shipping. I know your man-headed skeptical side wants there to be a catch. I looked for one too, I looked hard and there isn’t one.

Let’s say you have a wedding coming up in two weeks. You know you don’t have time to shop. You call your expert and say you need something for a wedding. It’s a 5pm spring wedding in the South and it’s going to be sweltering. Outdoor ceremony, indoor reception, live band, possibly shrimp cocktail or those stuffed mushrooms everyone loves. They send you an assortment of ties, suits, shirts, socks and shoe options that fit the social criteria. You keep what you like and send the rest back. Done.

You pay nothing for Trunk Club. There are no stylist fees. The prices of the clothes are standard retail prices. The best part though isn’t one that’s publicized… there is no buyer’s remorse. If you don’t like the item you bought several months ago, you send it back for a full refund… regardless whether or not you’ve worn it. Also there’s no minimum order and you can schedule times your expert as often as you want, forever. There is absolutely no pressure to buy anything.

One e-mail sent. One package arrives. No shopping time. No return time. No pressure.

The few setbacks I experienced were due to the ridiculous FedEx delivery route in my Los Angeles neighborhood, combined with my building’s buzzerless front gate. It resulted in a car chase to hunt down the truck for my pre-scheduled stylist meeting (of course, I could have rescheduled, but what is a man without his word?). Beyond that, I couldn’t help but feel like I should keep everything my stylist sent me. The guilty feeling of saying, “I don’t like it,” or, “It’s great but I don’t need it.” remained prevalent in my mind.

The single biggest drawback is that the clothes are full price. I’m a huge fan of consignment stores or, at the very least, the sale rack at Banana Republic. It’s not that I don’t darken the doorway of a department store from time to time, but I’m more likely to be found at Nordstrom’s Rack or a few of LA’s great second-hand stores. But the absence of sale prices is replaced with spot-on, regret free and stylish wears, with access to a personal stylist and products you never knew to look for. You buy less, but you buy better, and that’s something I can appreciate.

Trunk Club’s flexibility to meet wherever and whenever is a major boon. Your laptop is suddenly a direct portal into the world’s best styles for men. The process is essentially free and using a webcam and a personal stylist creates an experience incomparable to scrolling the pages of a website. You’re inevitably going to purchase new clothes, so why not let an expert help you do it for you? Trunk Club is a jean-ius way to shop.

Learn More About Trunk Club