Dress Like a Gentleman: A Look at Men’s Style Boxes

By Dave Johnson

Something has happened in the last decade: Across all occupations and budgets, men are dressing better and they are realizing its importance. I personally had an almost Jedi awakening when my kids were born and I realized I needed to dress as an example for my kids. But I had a problem—a big problem: I had no idea where to start, or even if I could afford the clothes that I presumed I needed. Although I haven’t arrived, I continue along the path to dressing better, and over the last couple of years I have significantly changed my wardrobe for the better.

The first service that helped me was Cladwell.com. Cladwell is a website that helps men
and women build personalized, minimalistic wardrobes by highlighting the essential clothing needed for each season. They ask many questions about your style, comfort level, climate, and coloration, and then determine which clothes work best for you. They suggested my color palette is “deep winter” (dark colors), and my style is “casual guy.” Good to know! It’s an outstanding service and was a revelation in my personal journey. And for $7 a month, it’s a steal.

But I realize that even Cladwell has its limits. Not every man has the time (or desire) to shop for the clothes he needs—including me. Besides, just knowing the right types and colors of clothing, I needed clothes that fit, which apparently is a constant battle with my body type. I personally hate shopping in stores, so I needed an alternative. On top of that, I had to factor in affordability since I’m not Tony Stark, and I have to be budget-conscious. Thankfully, the fashion gods had me covered: subscription clothing services.

Personally, I believe one of the best services to come out of this men’s fashion renaissance has been that of online box subscriptions—and that is the focus of this article. These have been a great asset to the wardrobes of countless men, mine included. These services cater to men who desire to dress like a gentleman, but who might lack the knowledge, time, or the budget to do so. So I want to give an overview of some of the most worthwhile choices.

Chief among them is Trunk Club. Trunk Club’s service is simple: at no charge, they connect you to a personal stylist to assess your needs and then send you a box of clothing. You only pay for the clothes you keep, and send back the rest, postage paid. Trunk Club is a fantastic service with clear pros and cons. The benefits are obvious: free stylist—and that alone is impressive. The main con is the price of their clothing. From their website, “Jeans are $170–$250 per pair, casual shirts are $100–$200 each, and sweaters are $100–$300 each.” Ouch. In their defense, they have over eighty top brands, and they ship top quality clothing, so if that’s in your budget, Trunk Club is the absolute best. If you can’t swing that (like me), there are other great options.

Five Four’s service tweaked the Trunk Club model and made it more affordable. You fill out a questionnaire about your sizes, color preferences, and style. Then, for $60 they send you in-house designed and curated clothing every month—you keep everything at no additional charge. You will receive 2-3 items with every shipment, appropriate for the corresponding season. I was unsure how well this service would be for me, but after getting my first “box” (really just a bag), I was pleasantly surprised by the quality and styling of the clothes. I received two boxes worth of clothes, and in them were two Henley’s, a t-shirt, jeans, and light jacket. I liked everything, and it all fit perfectly. For someone more budget-conscious, I think Five Four is not only an excellent value for your money, it’s a fashionable choice.

My first exposure to Fashion Stork was from a video recommending their service. What really stuck out to me was not only their service, but their mission, which is to donate to families wanting to adopt. Their service is somewhat of a blend of the previous two suggestions: you pay $75, keep all your clothes, and you connect with a stylist who curates your clothes. In my box, I received a sweater, shirt and tie, and a note from my stylist to pair it with jeans to complete the outfit. I was really impressed by their service, professionalism, communication, and most importantly, the clothing they offer. With every box sold, they donate $1 to fund adoptions. As someone with friends who have adopted, this company really hits home.

In my search for subscription boxes, I found some companies doing things differently. Urban Dapper’s business is only ties. For $14 a month you get a stylish, high quality tie. The sample I received was a highly fashionable navy and white dotted tie. The value and quality here is wonderful, and if you wear ties a lot or just want to beef up your tie collection slowly and affordably, this is perfect.

Touted as the “#1 Men’s Subscription Box,” SprezzaBox gives you a box of goodies worth over $100 for only $28 a month. You’ll get items like ties, socks, grooming products, pocket squares, and other fashionable accessories. My SprezzaBox included a tie, pocket square, toothpaste, socks, and a shoe horn—each piece exuding quality. The value here is off the charts, and the quality and variety is really wonderful. Even their web store is great, selling all the items they put in the boxes, and offering them at competitive prices.

Lastly, Scent Trunk is fragrance-centered and at $18/month they send you three personalized fragrance samples based on a profile questionnaire. I have found this service really helpful, and they send scents I like all the time.

There are countless other services like these out there and is impossible to review them all in one article, but these few are some of the best. Men everywhere are dressing better because of these companies, myself included. It should go without saying, but I was really impressed by all these services, and if it means anything, I highly recommend all of them. Truly, it has never been easier to dress better, and we don’t have to break the bank to do it.

Timeless Timekeeping

Unlike clothing, watches are accessories that can last for decades. The value you get from a watch; therefore, is immensely greater, even if the initial cost is higher. To complete your look, I suggest the Lum-Tec Combat series. This particular model is the B26, but anything in that series works wonderfully. Lum-Tec makes exceptional limited-edition, American-made watches with premium parts utilizing a friendly and approachable military feel. They are versatile and sensible with their classic styling and two included NATO straps, plus they work with many outfits. And, of course, the luminosity is very bright at night. The pictures are great, but it’s even more impressive in person and has a legitimate “wow” factor. At $495 it isn’t offensively expensive and has the build quality to last the rest of your life, and do so with timeless style.