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Trunk Club's VP on Why Men Should Wear Tapered Jeans

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Jason Smith knows a thing or two about style. As VP of Product Merchandising at Trunk Club, the local men's personal styling service that recently partnered with Esquire, he spends his days immersed in the world of fashion. But he still insists that his vision for Trunk Club has way more to do with personal style and presentation than it does with the fashion industry.

Smith believes that men should put their best, most impeccably clad feet forward every day, and a big part of that is dressing to impress. Here, he tells us why he loves doing business in Chicago, explains the flattering powers of tapered jeans, and lays out why no woman should ever buy clothing for her boyfriend or husband.

First and foremost, do you have any favorite places to shop locally?

Are we talking about clothing? Because if it's clothing I only shop at Trunk Club.

What about accessories, shoes?

There is a place on State Street that I love called Posh. Whenever we're looking for gifts for people's homes or something special, we shop there quite a bit. We go to the DOSE Market quite a bit, but that's about it.

Do you have favorite designers?

Yeah. In terms of jackets, I'm really liking the L.B.M 1911—that whole garment-dyed, unstructured look. I travel a lot so some of their pieces are really great for me if I get stuck on an airplane for four hours. I can wear a jacket, a blazer, and feel fantastic. It's dressed up enough for me and still has a casual edge, which I really like. And then Eton shirts. I can't find a better shirt in the marketplace. I think it's the only shirt I wear these days. They guarantee the color will stay for like ten years. The fit is just perfect, great materials.

Local guys: The Oak Street Bootmaker guys are just wonderful to us, so I think pretty much every shoe in my closet is from Oak Street Bootmakers. They've made some one-off pieces just for me, which is really, really special. They're just good guys. Chicago—it's just not New York, it's not LA. There's a lot going on right now and so we root for a lot of local brands that are trying to do the same thing we are in terms of local business.

You guys must do a lot of demographic research here. Is there stuff you've found about Chicago that you think some people wouldn't expect?

I've lived in a lot of different places. I've lived in New York, Atlanta, DC, LA, San Francisco and now Chicago. I think what people are surprised by—at least what shocked me—is that the taste level here, the general aesthetic here, is really stylized. People really do care about how they look. If you go to San Francisco they really just don't give a shit. My friends that have moved from New York to San Francisco have just been blown away by how casual the dress is. So we've been really impressed and happy to see how many guys really do appreciate what we're doing.

Especially different neighborhoods and the different looks in them. Trunk Club is a national service, so we really have to pay attention to data and we can't just fall in love with one city's aesthetic. Things that are very important in LA are very different here.

What's something that sets Chicago apart from all the other cities?

There's a willingness to help here. Honestly, the guys that have come through our doors at Trunk Club have been so wonderful to us. They come through and the door opens up and they're like "What is this place? Is it Willy Wonka's chocolate factory for clothes? I don't get it." And then they see a bunch of people working really hard and trying to grow something special here in Chicago, and they ask us how they can help. There's just a wonderful generosity and spirit about Chicago that I haven't encountered in too many places. There's this wonderful humbleness; it's not arrogant by any means. We're very fortunate that we're here and growing here.

Something you always hear for women is "Dress for your body type." Do you think that advice is as important for men to consider?

It's becoming true for men. We have larger gentlemen, guys that you would assume don't even think about fit, that are asking for slim-cut shirts. The great reveal in menswear right now is that yeah, fit matters. It's the cornerstone of how we buy. We have to buy for different body types; we have to keep fit in mind when we're thinking about our units for each coming season. We have different brands for taller guys, different brands for guys who don't like fabric clinging to their bodies.

You have to think of fit. It's been nice to see men adopt what the Europeans have known for years, which is a well-tailored suit and a well-tailored shirt, something that fits your body type, just goes so far. We see it here: A guy puts on a shirt that isn't baggy around the waist and he looks at himself a little differently. It's fun to watch.

Do you have any specific tips for certain body types?

Double-breasted jackets are all the rage right now but they're not right for all body types. You can't be too bulky or barrel-chested. You should be a little bit taller and leaner to pull that off.

I would encourage more gentlemen to take on the straight leg jean. I think for a lot of the Chicago guys we've heard, "Oh, I don't want to wear skinny jeans." It's not that they're skinny, it's that they're tapered. It's got a slightly smaller leg opening. Getting guys to try on something like that, where they might frown and say like "Oh, I played hockey in college, my legs are too big to wear those skinny jeans," but actually they look fantastic. There's nothing better than a v-neck sweater or a v-neck t-shirt to just break up the transition face to neck to torso. It elongates him, it makes him look even taller. There's some tricks that the stylists know.

Do you think there are a few items that every man should have in his closet?

There are a number of items that every man should have in his closet. My closet is pretty extensive based on my role here at Trunk Club, but there are a few essentials:

·Every man should have a blazer. E very man should understand how powerful and important that is, how it can just dress up or down depending on how you wear it.

·A good shoe rotation. So much of menswear is taken from the women's market. Women have known about accessories and shoes for so long and it's good to see men finally learn to adopt it. A good pair of suede wingtips, a great driving moc, a great cap toe.

·A crisp white shirt. Tom Ford made a life of wearing that same pair of pants and a beautifully pressed white shirt everyday. There's nothing better than a crisp white shirt on a gentleman.

·Just a clean pair of dark denim. Denim is ubiquitous these days. Back in the day you couldn't go in to certain restaurants or attend certain events in denim but now you can pretty much go into the nicest restaurant and they'll be fine with you wearing a sport coat and denim.

What would be your advice for the guy who has no real interest in fashion but really needs to update his look?

It's not really about fashion and trends and what's going on in the marketplace. It's about how you look and present yourself. Back in the 80s and early 90s, status was about which Porsche you drove, but you get off of work and you park it in your garage and no one sees it. But a good haircut, a shave and clothing and fit, things like that?.that's how you go through life and that's how people read you when you meet them.

Last question, and this is for our female readers: Is there one item, either a piece of clothing, or any other item, that you'd recommend the women buy for the men in their lives?

I love it when my wife buys me something special. Usually that's an accessory, like a bag. It's an investment piece. I'm a big believer in watches. Time is ubiquitous, but the passage of time means something to me and I love wearing a watch on my wrist. My wife helped me pick out my watch and every time I look at it I do indeed think of her. If she's helping him pick something out it should mean something.

I feel like clothing is like artwork. When your friends show up at your house with a painting it's like "Asshole, I want to design my own house." I would say that if there's something special, an accessory, a watch. Shoes, too. Women just know shoes. We always tell guys that the first thing she's going to look at when she sees you is your shoes, so I'd absolutely lean on my wife or girlfriend to help me pick out shoes.
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