Five Fits With: Menswear Legend Sid Mashburn

I probably need not say much about Sid Mashburn because if you’re interested in this column, you’re likely already familiar with his name, shops and products. The man is an absolute legend, and I’m honored to have photographed and interviewed him yet again. If you haven’t had the pleasure of meeting Sid, I can tell you he is as you imagine: charming, funny, smooth, and wholesomely nerdy about menswear. Most times I’ve met with Sid, we’ve started at a trunk show of his here in Manhattan, and every time a customer, new or old, wishes to meet him, he drops everything to chat with them for a few minutes and make them feel welcome. And I’m not talking empty chit-chat; he really understands how to have a conversation, and then some.

Below, Sid and I get into some personal history, and how he took Sid Mashburn from an idea to five stores. We tackle some useful topics like big event dressing, items every man should own, packing for a flight, and plenty more.

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We’ve gone in-depth elsewhere before, but I’d love to bring some of that information to Esquire’s readers, so can you tell me a bit about how you found a passion for clothing, and some of the places you worked along the way to starting your own brand?

Growing up in Mississippi, I was always around clothes. I had an older brother and sisters who loved clothes and fashion, so along with sports, that was the other huge interest for me. As early as junior high, I was experimenting with my clothes, asking my mother to either take the collars off my shirts, or peg my pants. Nothing too crazy, but I look back now and it’s funny to think about what I walked out the door in. As soon as I got my driver’s license, I went to work for a cousin of mine at Busick’s in Pearl, Mississippi. I thought I had won the lottery; working inside, stocking, folding, and selling clothes to nice people—it was the best. After college, I headed off to NYC where I really hit the lottery by getting a job as the first menswear designer at J.Crew, and then went on to design for Ralph Lauren, Tommy Hilfiger, and then led design for Lands’ End. And then in 2007 my wife Ann and I moved to Atlanta to start our own thing…and here we are.

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

Talk to me about the process of scaling Sid Mashburn up, from your first shop to the five you have now. How do you keep your brand messaging and ethics the same across the country?

We started with a dream to have more than one shop filled with our own designs. But we’ve always taken it at our own pace; we are particular about the makers and vendors we work with, often they’re smaller, family-owned companies. Today, 90 percent of our offering is our label on the men’s side, and the women’s side that’s more like 80 percent. Managing the design, merchandising, manufacturing, and our brick-and-mortar and e-commerce shops takes some thoughtful navigation to just maintain, let alone grow.

A big part of scaling the brand messaging is through employee training and our monthly store set meetings, where we talk through all the new items for the month with our store, web, and customer experience associates across the enterprise. We’re always working to improve, but in particular we talk a lot about hallmarks of quality and make, design philosophy, and commitment to high-touch service. And our core values, too: hopefulness, helpfulness, hard work, honesty, humility, and honor. Sounds kinda lofty for the clothes business, but we try to imagine ourselves in the minds and shoes of those who let us take care of them. Our first business cards had “Vestitum et sanae mentis” which means “Clothed and in his right mind.” That’s how we want to leave guys. Ultimately, we want to enhance people’s lives through what we offer—clothes with the best quality, value, service, and style—so we can help our customer enjoy an economy of time, mind, money. And frankly, confidence.

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

I would love to know what style rules you have for readers, and which items you think every guy should have in his closet.

Style rules…it sounds funny, but I don’t have a ton of them. I guess it helps that I wear a uniform—a jacket and tie—because it actually minimizes your decisions in the morning. The tie is my hardest decision of the day! But ultimately, dressing is about good manners, so rule one is to make an effort for those around you. I can attest that having a store you like, with great products and a great tailor, helps with that. Beyond that, I’ve always endorsed the motto “I am too poor to buy cheap.” I love thinking about the cost per wear, and factoring in the enjoyment you’ll get out of it. So I have always tried to buy the best quality I could afford.

As for the items I think every guy should have in his closet? Internally, we talk about a starter “kit of parts,” which is a matrix of 10 essential items that give you a lot of range. The idea is that if a guy has these 10, he can basically mix and match his way almost anywhere in the world.

Sid Mashburn's Kit of Parts

This roll-up might seem basic, but it's super versatile; it all works together wherever you live. If you've got a wedding, it's navy suit plus white shirt plus navy tie plus dark socks plus the lace-ups, shined. If it's casual dinner, it's dark jeans and the blue-striped shirt, sleeves rolled up. If it's hosting a client for a cocktail hour it's gray trousers, navy suit jacket, and sport shirt—maybe go sockless. Most any scenario, you're ready.

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

What do you think would be a perfect first date outfit? Do you remember yours?

For a first date, I’d consider your age, the occasion, and where you’re going. (You know, going back to that first style rule.) A pretty safe bet would be a clean, un-ripped, well-fitting pair of 5-pockets, dress shoes, and a dress shirt. Or at least a shirt with a cut-and-sew collar. If it’s a little on the nicer side, a tailored navy blazer is never a bad idea. Whatever it is, it’s just gotta make you feel good and give you some confidence. It’s always a good idea to dress a bit better than you think would be “good enough.”

Not sure about my first date, but I remember I was wearing floral swim trunks and puka shells when I met my wife Ann. We were at the beach on Long Island. Again, it’s about what makes you feel good, and floral prints and beads always make me feel good. That rule doesn’t work every time, but it worked that day.

Are there any brands outside of your own that you appreciate, and if so, why?

We tend to look outside of retail and especially at companies that place a high premium on serving their customer by thinking through what their needs are. A few of those are the Hillstone Group, the original Ritz Carlton, Danny Meyer’s Union Square Hospitality Group, the Masters Golf Tournament, Chick-Fil-A, Tesla, and Trader Joes. From a retailing and service standpoint, I think about retailers in Italy and Japan; they’re often really detailed oriented, put a premium on quality, value, and craftsmanship, and take pride in their work, and taking care of others—all things we aspire to. And we built our business carrying great brands we believe in—Alden, Filson, Edward Green, Gränsfors Bruk, Randolph Engineering, Timex—which we still carry today.

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

I was told by your team you’re wearing a new piece today. Tell me about this piece, because I’m personally obsessed with it. And what’s the process like for you all in designing new garments?

So glad you like it. It’s called our Ghost Blazer, and it’s been a looong time in the making. Growing up trying to find my style, I was almost always in some kind of jacket: a jean jacket, a hunting jacket, a butcher’s coat from my friend’s job at the meat market in the Jitney Jungle, or a super-simple cotton blazer I loved from Willie Smth’s Williwear line. This is where that easy, throw-on jacket idea meets a tailored piece that can take you anywhere.

We took one of our all-time favorite fabrics—a two-ply, high-twist wool from England—and made a blazer in that fabric that is totally non-structured and casually elegant. It has these hybrid patch pockets that allow you to tuck in the flaps so it looks like an open patch. It’s also got these beautifully cool sand-cast brass buttons from a small button maker in Italy that replicates a wax seal. We wanted it to look totally at ease—and make you feel like that, too! We made the prototype last spring, and I have been wearing it probably two-plus times a week since. It’s one of my favorite pieces we’ve ever made. I hope other guys like it; it sold out the day we put it on the website, but we’ve got more coming in. It’s a forever kind of piece.

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

sid mashburn

Christopher Fenimore

You travel a lot for work, so can you offer any packing tips?

For me, the goal is to get everything into one carry-on, with one zip-top canvas tote. I am usually on business, so I bring a suit typically, but you can skip that and get away with a jacket—navy or something discreet. I like to wear a jacket on the outbound flight; it doesn't wrinkle as much, gives you a leg up on a possible upgrade, and all the pockets make it function like a man's version of a purse.

I always pack a small dopp kit along with the usual suspects: a white shirt (in case something formal-ish comes up), a solid tie, a pair of white jeans, a pair of blue jeans, and a pair of dress shoes that can be dressed up or down. Even if it's not fall or winter, I typically pack a lightweight sweater: a fine-gauge cashmere crewneck. And, no matter what, a swimsuit. It's the biggest disappointment when you don't have it. Be ready always…to go swimming.

In my tote—you want one with a zipper so you can put it underneath your seat without anything falling out—I put my computer and cords and adapters, a folder of work stuff, my sunglasses, some reading materials that I may not get to, plus some pens and something to write on.

And as for tips, I have a few formulas. I take one additional shirt for every three days I'm gone—four for a three-day trip, et cetera—and I get them folded in plastic when I send them to the cleaners because they are easier to pack. For jeans, I will turn both pairs inside out, and roll them up so the white ones avoid getting stained and the indigo ones don’t stain other items. I'll usually bring a pair of shoe trees, but those things are heavy, so in a pinch, you can put some rolled-up socks and underwear in your shoes instead. It works almost as well.

What is the ideal weekend outfit for Sid Mashburn, and your ideal weekend activity?

On Saturdays, I like to suit up and go to the office and shop when I’m in town. I love the vibrancy of the shop and spending time with the team, customers, friends, everyone…it’s hard to beat. As for Sundays, I love resting: going to church, sitting by the pool (or the fire in the winter), listening to the radio station FIP, and doing the crossword. Maybe even taking a nap. Swim trunks in the summer and cashmere sweaters in winter are about as an ideal of a Sunday outfit as I can imagine.

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