If any new brick-and-mortar retailer focusing on quality footwear opens up in the US, it’s a story. But when that store sells Edward Green and Alden (including a deep forthcoming lineup of custom makeups) with plans to expand out from, and used to run Leffot Chicago for its three-year run? Well, that’s a really big story.

I sat down (sure we were halfway the way across the country from each other, but we were both sitting) with endlessly shoe-mad Dashing Chicago owner Sean Moran, who recently opened his new baby in the old Leffot space in the Loop.

Dashing Chicago — Alden

With damn near a decade of experience in the shoe retail game, Sean is ready to rock out of the gates with a curated range of Alden stock models—from Indys, to bluchers, to loafers (there will be a LOT of loafers at Dashing)—and has a grip of shop-exclusive makeups primed to roll out in 2022. Same with Edward Green: stock Dovers and Galways and loafers to start, but then custom creations coming in before long. Oh and maybe Paraboot!

Sean Moran Dashing Chicago — Alden, Edward Green

Very important: what shoes are you wearing at this very moment?

Well, I could lie to you and say something fun and unique like a pair from Hiro Yanagimachi, but in reality you caught me the one day this week NOT wearing an Alden loafer. I’m actually wearing an Alden 2160, color 8 shell cordovan, cap toe blucher on a double-leather sole. I wear them kinda beaten up, and I’ve always said this is a sleeper in the stock cordovan lineup from Alden.

What would you describe the overall philosophy and aesthetic of Dashing?

Well, in its current form—a couple months with the doors open—it takes inspiration from the pared-back aesthetic from my Leffot Chicago tenure. Longer-term: mid-century inspired, with a pop-art sensibility. I wanted to wrap the store in a cool regal blue, to give it a masculine, but comfortable feel. Whether that relates back to your favorite pair of selvedge denim or a navy sportcoat that’s just easy wearing, it’s about familiarity.

This business is highly one-on-one these days, and I want this to be a comfortable space that feels familiar…but with a twist. The days of a store being #menswear with wood trim and lines of shoes on the wall, in my humble opinion, are over. I want Dashing Chicago to be a bridge to the younger generation of clients coming from a sneaker or luxury retail experience.

Dashing Chicago — Alden, Edward Green

Obviously everyone buys shoes on the internet these days, but what do you think the Chicago customer is looking for but can’t find, that Dashing can solve?

FIT, FIT, FIT, FIT!!!! Sure, anyone can shop on the internet, and honestly it only grows the base of clients. That being said, 8 out of 10 guys mess up their sizing on their first Alden—at least that’s my personal experience going back to 2012 selling Alden. Plus, when you then look to upgrade into something like Edward Green or even Paraboot—which is also tough to try on—you can make a lot of costly mistakes.

I’ve learned to listen to what a client wants, ask a lot of really solid questions, look at their feet, and measure using the Satra measuring device I was exposed to via Edward Green. A bit of it is still experience and knowing how to convert it to Alden sizing, but you’re not going to hear this from a lot of retailers. I’d rather lose a sale than put you in a shoe that’s not your ‘proper fit’.

Honestly, it’s personal to me, and I don’t want to see you come through my door after two weeks complaining about the fit. I’d rather be up front, honest and get you what works…even if that’s not an immediate sale, then get you into something a half size too big or a width off because I want to make a sale for that day. If my client really wants something, I will gladly oblige, but for most clients, proper fit is vital.

Sean Moran Dashing Chicago — Edward Green

How would you describe Chicago style in 2021?

Hmmm…non-existent if you want to put a label on it. Overall, Chicago is midwestern; it’s always the classic cotton trousers/denim, button up shirt, too light of a color shoe (normally too big), and boots or sneakers. You do get the pocket of folks that only shop up in Gold Coast, so it’s all ‘Label’ brands vs heritage brands. You do get the client in from other places that are psyched on Alden or Edward Green. A good friend of mine—Kiyoshi Martinez from Hall Madden—made a really solid observation recently: “After Haberdash closed, no one rushed to fill that huge void—that’s super telling about the state of menswear in Chicago.”

You love loafers, and seem like you’re going in heavy on them with Dashing. What’s a loafer mean to you? What should it mean to others, and where do you see the bounds of how they should be worn?
This is a great question. At the heart of it, I don’t wear sneakers or gym shoes, except to run or to go the gym. I wear loafers. I didn’t even wear them that much till I opened my friend Anastasia Chatzka’s store. I had a few pairs of cheap loafers I just kept reaching for day after day—one being a canary red suede—and it kinda just went from there.

My first Alden was a pair of 660’s. Black calf, tassel loafer, nothing exotic. But I was hooked. 
I see loafers as the perfect gateway for the younger generation of guys getting into heritage footwear. I have guys in the store in Chicago that haven’t pulled on a ‘real’ dress shoe since they were like 10 and forced to wear it to a wedding or something. We have a HUGE generation of people that only know sneakers. But I don’t care how casual an office gets—loafers are the perfect way to make your aesthetic simply set you apart. Hell, they even look cool with a pair of joggers if you get the correct aesthetic of loafer. John Lobb does a great job with their Lopez and newer Thorne. I also really like what Baudoin & Lange is doing with their Sagan.

I’m a die-hard Alden loafer guy, and I have plans for some fun Edward Green special makeup offerings for Spring 2022. Even one that harkens back to that loafer that got me hooked.

What’s your personal favorite shoe of the moment that you sell, or will sell, at Dashing?

This is a tough question, as personally I still love my Hiro NST in brown suede. That one ranks as my favorite of all time. I don’t own an EG Dover (yet), but wanted to go with Hiro for something personal to get into that aesthetic.

I really want to do a color 8 Edward Green Windermere (color 8 PTB) for the store, but do it on the 202 last, and on a rubber R2 sole to give a more refined version of the Alden 990 aesthetic. I’m excited to offer something like that. It’s on a more versatile sole than what Alden can offer. But on that R2, it’ll just have this more modern vibe—the R2 is a double rubber sole with leather forepart middles that taper to single rubber sole and are beveled a bit at the waist.

A shocker for me was the Paraboot Reims that I picked up in 2020 from Style By Blain in navy leather. I was curious how they fit, broke-in, etc as I always dug the aesthetic of the shoe and Paraboot’s classic lineup. I ended up LOVING IT! I wear the Reims a lot, and it’s permanently at my loft entry way to slip on to run around to do errands or head out for a weekend adventure. I had a great visit with the rep at Chicago Collective and think I’m going to bring a lineup of Paraboot into the store for late-spring/early-summer 2022.

Favorite boot?

I am admittedly not a boot guy. However, even before Leffot Chicago opened I saw Edward Green release the Kentmere, and I WAS HOOKED. It’s an updated take on a rugged strapped field boot. The version I have is 72 last, dark green Utah leather, Ridgeway sole. It’s a total shit-kicker/’fuck you’ boot in my opinion. It has all the trimmings of the Galway, but the straps just make it more badass. The lasts from Edward Green really work for my foot, so I really lean into Edward Green boots. I think they do a great job, and have a list of grail makeups I’d like both for Dashing Chicago and personally in the future.

Dashing Chicago — Alden, Edward Green

If you could do any Alden makeup you wanted—Alden isn’t telling you no, and you don’t even have to worry about selling them or anyone else but you liking them—what would it be?

To be 100% honest with you, Alden was very accommodating of my 2022 special makeup selection. Without giving anything away yet, I requested two twists on a current stock model, and they agreed to make them—one’s been done for an Asian market retailer, and the other something “new”. I truly thought they were going to say “thank you but no sir” to one or both of them.

My Alden rep, Brett Klein, is amazing, and we have a great working relationship. He’s got a fantastic finger on the pulse of the Alden world, and I think the best part of our working dynamic is that he knows my tastes are different from a lot of other Alden retailers out there. The first special makeup order for 2022 went VERY smoothly and only a couple changes were made due to one pattern not working, and another shoe simply kinda missing the wave of popularity and I actually pulled the plug on it. Honestly, the two replacement models we came up with create an even stronger model lineup for 2022!.

I guess the de facto easy answer would be an endless supply of rare shell cordovan makeups, but oddly enough, if you want something bad enough, you can simply pay the premium and get it from Edward Green or the like.

Having a Leffot in Chicago was a huge thing for shoes in the city and physical footwear retail in general. But it didn’t work out. What do you think is different about Dashing in terms of your outlook for sustained long-term success?

Running multiple physical retail locations is a very tough endeavor, period. I saw it first via my four years at Haberdash, and again via Leffot. Inherently, there doesn’t seem to be much trouble. But when it really comes to the rubber meeting the road, it’s a tough undertaking. 

The Chicago retail experience & shopper is dramatically different than those who shop in New York, or out West for that matter. New York is a shopping “holy land”; you want it—you can find it!

The midwestern client is more of a consultative experience. Sure, you’re going to get the client that walks in, sees or knows what they want, and it’s a done deal no problem. My experience is, a lot of Midwestern clients do a TON of research, want to see things a couple times, get fit to confirm or correct all the “knowledge” they acquired online, and finally they pull the trigger on the shoe or boot. To be honest, I can 100% appreciate that, and enjoy explaining things and walking clients through the lineup.

Dashing Chicago — Alden

My three key principles for Dashing Chicago are: Inspire, Educate, Fit. Now, I’m not saying other retailers don’t focus on those topics, but I’m making them the key to what I do. This is a marathon, not a sprint, and I 100% admire the tenacity and vision that Steven at Leffot has shown through the years. I want to offer you the best heritage shoes, but with my own personal twist. I’m more of a shoes and loafers guy, but I will definitely sprinkle in some fun boot makeups.

I think with age one realizes that at a certain point you have to embrace your strengths, and simply minimize your weaknesses. Trying to do everything maxed out simply isn’t possible, especially in today’s marketplace. Plus, the market for men’s heritage footwear is changing. I have some plans that I’d love to work on in the future that combine a more luxury digital experience you’d see from larger brands, and to not be afraid to leave the four walls of Dashing Chicago for special launches, trunk shows, events etc.

Huge thanks for the chat Sean. Now go sell some great shoes to tons of people please.

Oh I’m on it.

Check out what Dashing has got going on

Dashing Chicago — Alden, Edward Green