style questions | The Style Guide

Editor’s note: To catch up on other Style Q+A entries, start here.

Jamal Jackson, of StyleSocietyGuy, is a recognizable face with a terrific sense of personal style.

The great and exciting thing about living in a place like New York City — or really, finding a community filled with like-minded people anywhere — is how many different people you get the chance to cross paths with, through either personal or professional interaction, or both. I’ve been really lucky to learn a lot from so many great people since getting interested in the menswear world (most of whom have been profiled in Style Q+A pieces!), and that list grows by the day. Through attending events as part of the GQ Insider community, and through some work we’ve done together as part of my day job with Timberland Boots, I’ve had the chance to become close friends with Jamal Jackson, also known as StyleSocietyGuy. As we’re in the midst of New York Fashion Week: Men’s here, you might recognize him from his extremely well-curated Instagram or his Web site , where he offers up a bevy of menswear styling suggestions, new brands to watch and lifestyle content focused on things like home design and music. And of course, there’s the small business of Jamal topping Mr. Wooster (and other well-dressed dudes) on Esquire.com’s rundown of the best-dressed guys at New York Fashion Week: Men’s this past summer. Moreso than that, Jamal is a great guy, a heck of a friend and one of the best in the business at partnering with established and up-and-coming brands and telling cool stories.

And as with every day in the digital style universe, it’s great to be able to look at what someone else is wearing, or how they’ve styled a certain item, and draw inspiration from that — even if their personal style is a bit different than yours. So with that in mind, I caught up with Jamal to find out about running his site and how he charts — literally — his very busy days. Enjoy!

The Style Guide: How did your personal interest in style and fashion get started?

Style Society Guy: My dad has always been into grooming and style. Mostly, he had grooming and excellent hygiene, so my interest in menswear grew from there. I’d say I really started getting into it in middle school .

Your Web site and Instagram presence is impressive and seems to grow by the day – what’s that development been like? (Editor’s note: Find Jamal on Instagram here).

SSG: I noticed that I have spurts in my stats …but I’m noticing that it’s mostly organic — just how I wanted it to be. The downside of it is that I don’t know exactly who referred a visitor to my site until someone tells “Oh, (my friend) told me to check out your site.” I wish I could measure those stats more but it makes me want to strategize how I produce my content everyday.

TSG: On that note, what’s a typical day like for you?

SSG: This might sound kind of crazy, but I work from one Excel sheet. I have several columns in that one sheet — every day of the week and what I should be doing hour by hour. It sounds kind of stressful but it really disciplines me. Although I don’t follow every single task at every hour, it’s a good guideline to … keep me on track.

Right now, I’m working at a work space called Projective in Freemans Restaurant in New York’s Lower East Side. I don’t have a specific office spot except for home at the time, but I’m good at documenting as I travel.

The day consists of meetings, video calls, press previews (whether it’s a market week or not), webinars, nightly events, and usually dinner with potential clients or digital friends.

Jamal also frequently works with top-flight brands during trade shows and manages his own growing social media platforms.

TSG: On that note, what’s something that people might not know about running a Web site and digital presence like yours?

I think this is a common answer, but I’m going to say the amount of work it takes to produce one post. From the outside, it seems like what it takes to create a blog post is to take the photos and write about what you’re wearing. However, it is far more than that. You need to plan to not wear other competitors in one post … speak on details of the clothing, amplify the brand’s voice and speak to the focal point of the product and the brand. Another aspect is how long it takes to shoot photos, gather your photographer and edit 350-450 photos 3 times a week.

Jamal as seen on the street during the first-ever New York Fashion Week: Men’s this past summer (Esquire.com ranked him #2 in its weekly rundown!).

What’s the biggest change you’ve seen over the past few years as far as the menswear community goes?

I’m seeing a lot of guys being comfortable with showing their personal style and grooming regimens. Its actually ‘a thing’ now. I love that menswear influencers can bring readers to share what they’re are wearing and interaction going, brands are also happy with this as readers give very honest feedback on products ..bascically for free. This is a good time for brands to actually listen up and pay attention to what audiences have to say.

TSG: What’s one item (or perhaps one outfit) every guy should have in his wardrobe?

SSG: A denim or chambray shirt, I swear it works with EVERYTHING.

TSG: What’s one style resolution that you have for 2016 looking toward the rest of the year?

SSG: As of now I don’t have one set in stone. But. I plan to actually start wearing more of what’s buried in my closet, the items that still have tags on them. I tend to wear my favorites because…they’re my favorites.

To see what Jamal’s up to on a daily basis, head to the StyleSocietyGuy Instagram or check out his Web site.

Editor’s note: To check out other Style Q&A pieces, head here.

Just a snapshot of some of the eyecatching styles produced by American Trench. Photo courtesy of the brand.

You can’t help but admire brands that delve into a product niche and ideology, and really live out that commitment. Jacob Hurwitz and David Neill have done that and then some as they’ve built American Trench, a brand with whom you may be familiar if you’ve read any of my work on VOUCH Mag — or if you’ve seen their socks in GQ. The duo developed the brand with the simple idea that manufacturing high-quality goods can be done right here in America, and they’ve stuck to it with the help of a Kickstarter launch in late 2012. I had the great fortune to check out a set of excellent American Trench socks for a review on GearHungry (and you can expect to see more of them around these parts, too). The socks are eyecatching, comfortable and quite well-made — everything you could want on your feet. And in corresponding with Jacob, he and David have a tremendous focus on doing right by the people they work with — something to be applauded and recognized. The brand makes a pretty killer trench coat, to boot. I caught up with Jacob for a few questions recently, and the interview is (I think) absolutely worth a read if you’re into supporting brands who take care of their own — and make a pretty nice product, to say the least!

The Style Guide: Tell me more about the inception of American Trench and the ‘A-ha!’ moment that spurred it on?

American Trench: I took a trip to London with my wife in the summer of 2009 and bought a trench coat there, because when in London, one must buy a rain coat, even in the summer. After getting home and reading day after day about continuing layoffs and job losses, my friend David and I were talking about US manufacturing. We wanted to make something. The idea came up…who makes trench coats in the USA? The answer – no one. So we set out to do it. We had no experience in apparel, so it took 2.5 years, but we make something special.

TSG: American manufacturing is at the core of your business — expand a bit on your philosophy behind that commitment to domestic manufacturing, and are there other brands you admire doing similar things?

AT: American manufacturing is why started the company, plain and simple. All of our products are either knit or cut and sewn in the USA. We try to use domestic source materials when possible and appropriate, but each item has been manufactured at a factory in the United States. Our philosophy can be summed up pretty succinctly: make the best you can make and do the best you can for the people around you. When we read about Brunello Cucinelli’s desire to make all of his products in Italy, which is well documented, it doesn’t sound nationalist. He makes it very clear that this is how he can best help the people around him. The best part about buying USA made? It’s totally in alignment with the core principles of our country – freedom and liberty. Buying USA made is not mandatory nor does it require belonging to a specific race, class, group, or political party. In the land of liberty, the greatest freedom we all have, what we choose to buy, can actually can create change! So there it is — vote with your wallet.

The brand’s relatively understated styles add a nice touch of color to any outfit. Photo courtesy of American Trench.

TSG: American Trench has a pretty particular product focus between knitwear, socks and your outerwear — how did that come about?

AT: We decided to launch a Kickstarter campaign to bring our trench coat to market and realized that we wanted to have a way for people to support us on Kickstarter even if they didn’t have $700+ to drop on a rain coat. So we decided to offer USA=made socks, because who can’t afford a pair of good socks? After Kickstarter, we started to get wholesale interest in the sock side of the business. People were looking for made-in-the-USA (product) and accessories, and we had both. We also found some awesome sock mills — one in Reading, PA and another in North Carolina. Interest in the rain coat never died down, so we become dual-focused on accessories and outerwear.

TSG: What was the biggest challenge (or series of challenges) you encountered in your journey to source fabric, materials and production partners for your trench coat?

AT: There have been challenges at each step, although that’s true for any business. Making the trench was a beast, we choose to make a super complicated product to start, with 70-plus pattern pieces. It took two tries to find the right factory, and not without a lot of screw-ups and fixes. Pattern making is not easy, nor is production. It’s a complicated business. Knitwear is not walk in the park either, samples and production sometimes don’t end up being the same.

TSG: What’s one style mistake you see too many guys make?

AT: Scale and proportion. If you going to wear slim jeans or trousers, the rest of the outfit should be slim. Then all items will be in proportion. You can’t wear your favorite decade old blazer with your new trim pants and vice-versa, the scale of each garment is totally out of sync. Likewise, sometimes a little looser look can be really refreshing, but make sure the rest of your outfit matches the same scale.

The other thing I would say is that less is more. Don’t cram too many colors, patterns, and styles into one outfit. For example — if you wear your double-monk shoes, keep the suit solid and the socks toned down; double-monk shoes are a big statement. Instagram style is its own universe, and should be taken treated as half-fantasy, half-reality. Less is more!

If you have square-toe dress shoes in your closet from ten years ago, thank them for their service and put them in the trash.

TSG: What’s one style-related item every guy should own?

AT: Tough one. But regardless of the item, quality over quantity. I think a good pair of versatile shoes is a must. I’m talking about something that can be dressed up or down, with a suit or denim. Great shoes make a good suit look great and turn your socks into a star. The Longwing 975 and PTB 990 styles by Alden are classic. They ain’t cheap, but you can wear them with anything. I really love the Rancourt cap toe as well.

That’s all from Jacob this go-round. If you’d like to support the brand more, check out their Web site or catch them on Twitter.

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Tag / style questions

Style Q+A: Jamal Jackson, StyleSocietyGuy

Style Q+A: American Trench