Meet the Chicago Guy Redefining Menswear Guidance

Seeking style advice comes in all shapes and sizes — but it used to be the exclusive domain of legacy media, the only voices deemed worthy of telling you what to wear. Enter social media. Platforms like TikTok and Instagram Reels let you skip the dry, page-turning slog of magazines and scroll straight through a portrait-sized parade of content creators — thumbs up, thumbs down, instant style gratification.

Today, who you take fashion advice from is entirely up to you. It doesn’t have to be a glossy publication. Sure, some creators are clearly in it for clout — or just free stuff — but then there are folks like Chicago-native Jabari Sandifer, whose style guidance on Instagram and his Substack, Where Your Pants Break, is rooted in authenticity, knowledge, and approachability.

It’s refreshing to see a Midwesterner educating the masses without needing a New York or L.A. zip code. “I like being the ‘Chicago guy,’ you know what I mean?” Sandifer says. He appreciates the tight-knit menswear community in his city and brings a millennial’s sensibility to navigating today’s style zeitgeist: “The internet makes the world smaller anyway, so as long as I keep doing my thing, I’m good.”

We caught up with Jabari to see how he styles our polo sweaters to tackle the autumn chill (whenever that decides to show up), how he got into menswear, the secret to mixing vintage with newness, and, most importantly, his go-to coffee spot in Chicago.

The Tie Bar: You’re a stylist and fashion consultant. What were you doing before getting into menswear?

Jabari Sandifer: So, I played basketball in college, and that was literally my whole life until I graduated. I got hurt in my senior year, but throughout college, I had started developing an interest in fashion. I knew I wasn’t going to the NBA, so I figured I should probably have something else I was interested in, right? I studied business, and after graduation, I went straight into retail. My first job was at Bonobos — funny enough, it was right by The Tie Bar in Chicago. I used to walk by The Tie Bar all the time. That’s kind of where it all started. I had some friends putting together makeshift photo shoots, met people, and just grew it from there.

TTB: For someone just starting to explore menswear, what’s the first item you’d recommend they buy? 

JS: I think pants. It’s hard to choose between trousers and denim — but denim is probably the best starting point. You know, I saw a recent article on the 501s, and those are probably the best place to start. They’ve been around forever for a reason. Obviously, there are so many different iterations, but getting a good pair of denim is essential because you can really build around it.

Next, I’d say either a good jacket or a pair of trousers — probably a jacket. But overall, denim is a really great place to start.

TTB: What are some of your favorite ways to style knitwear?

JS: I like wearing it with trousers, like a pleated, high-waisted pair. I love that — it makes me feel really put together and super comfortable. Even pairing it with a sneaker, or dressing it up with a loafer or a boot, looks really cool. That’s probably my favorite way. But I also love it with a pair of denim, dressing it down and giving it a super casual vibe as well.

TTB: Any tips for layering effectively, especially as we head into the colder months? 

JS: Yeah, I think the most important thing you can have in the colder months — especially here in Chicago — is a big overcoat. That’s my staple. Something with enough space. You know, there was a time when people wore those super-skinny topcoats, and you couldn’t fit anything under them. So I think having a roomy, double-breasted overcoat is essential, because you can layer sweaters underneath — even a thicker one. When it’s really cold, that’s key.

That’s my go-to. I also think it looks really cool to layer a lightweight jacket under an overcoat. That always looks sick. Overall, I’d say keep it simple. If you’ve got a great overcoat, it’s going to do a lot of the heavy lifting for you.

Personally, I run a little hot, so I’m not trying to pile on three layers. A good sweater and a solid coat can do all the work.

TTB: How do you style a sweater cardigan to get through those frigid Chicago days? 

JS: It's funny, because cardigans are probably my favorite layer. I actually just wrote about this recently — I love cardigans. They've been a staple in my wardrobe for years. I think they really toe that line between casual and dressed up, which I think is cool. They add texture, they're easy to layer, and most of the time I wear one with just a T-shirt and jeans, because you can never really go wrong with that.

Sometimes, though, wearing a cardigan with trousers feels a little too dressed up for me, so I don’t always love that. But it can work, especially if you’re going into the office or want to add some interest to a work look. Nine times out of ten, though, I’m throwing it on over a plain white tee or a graphic tee for more of a laid-back vibe — some Kurt Cobain-type energy, you know what I mean?

TTB: Can you share a few tips on mixing vintage pieces with new items?

JS: I think, for one, don’t overdo it. You know, sometimes I’ll wear all vintage, but most of the time I try to incorporate at least one vintage piece into my wardrobe. I think it adds a lot more interest. Vintage pieces are typically one of a kind — sometimes you’ll find repeats, sure, but not many people are going to have the same thing. I like having one piece with some patina, something that shows wear and character, to give a look more depth.

It’s also easy if you don’t have a ton of vintage in your wardrobe: just add one piece at a time. As you get more comfortable, you can branch out into bigger items, like an overcoat. Personally, I don’t think you should buy a brand-new wool coat — you can literally find one everywhere on eBay for a quarter of the price.

TTB: What’s one underrated stylish item you always make sure to have?

JS: I don’t know if this one’s a common one — it probably is — but socks. I mean, I think I’m kind of obsessed with them, and having good socks is so key to a great outfit. Especially when you can see them, or even if you just sit down and your sock shows a little bit, it adds that next level of intentionality. Plus, they’re comfortable too. Having good socks is awesome.

And especially as it gets colder, having a wool sock — or something with some texture to keep your feet warm — is essential, especially if you’re wearing loafers or something like that.

TTB: Outside of fashion, where’s your go-to coffee spot in Chicago? And for dinner? 

JS: I gotta shout out my homie, Andrew. Le Café is my spot. They have two locations — one in Bucktown and one in Logan Square.