We’ve all received (and given) bad gifts.

A few months ago we put our lady on the street, Cary Randolph Fuller, to the task of producing a guide for girlfriends (or wives) buying for their men. After some discussion, Ms. Fuller decided that a chat with J. Crew men’s stylist Jack O’Connor would prove fruitful. Below are her words and an insightful (and demystifying) Q&A. Many thanks are due to Ms. Fuller.

Several years ago, to commemorate a special occasion, I bought the (now ex-) boyfriend a pink and navy Ralph Lauren repp tie. At the time I couldn’t understand why he wasn’t thrilled, but age and experience have exposed the error of my ways. (And that error is: Neckties are kind of boring.) These days I steer clear of presents with seams and sizes, preferring to bestow upon the men in my life gifts that cannot be worn.

I’m not alone. Many women feel lost on the men’s floor. It can be hard to know what men want when a suit is not just a suit but a minefield of subtle intricacies. More often than not, we girls default to the necktie table or slink back to the women’s department with a gift card in hand. He can buy his own damn dress shirts.

Unless…I could enlist the help of Jack O’Connor, stylist for J. Crew’s men’s division and one of New York’s best-dressed. J. Crew has perfected the art of accessible fashion by marrying a well-edited selection of small heritage brands with its own collections. The results are always quirky and unique yet somehow instantly recognizable. To know J. Crew is to know the aesthetic and aspirations of the most stylish men and women. I recently sat down with Jack and his assistant Shawn Buchanan for a little primer on how to shop for the men in my life. Along the way I learned some valuable lessons for every woman who wants to give a gift that keeps on giving – the gift of great style. – Cary Randolph Fuller.

Above is a picture of Jack O’Connor. Read Ms. Fuller’s Q&A after the jump.

Cary: You’re at a J. Crew store, and you see women shopping with their boyfriends or husbands. What are some mistakes you notice?

Jack: I definitely see that. The guy thinks he’s a boot-fit guy, and the wife or girlfriend seems to think, “Well, he’s a boot-fit guy. He’s never going to stop wearing boot-fit jeans so why bother looking for something slimmer or something straight?” They think they can just narrow it down right off the bat and say, “Just show me your boot-fit.” I don’t think that’s a good call. It’s not the most flattering cut on every guy. Even if he thinks that’s the only cut he can wear because that’s what his friends wear, and that’s what he’s worn for ten years. She should probably bring him in, have him try something on and see for himself. We always keep that in mind when we put certain things together in the catalog and we choose who to put it on.

Some guys are afraid of “fashion” even those this isn’t really fashion. It’s more “style”. A lot of guys don’t want to look like they care too much. The idea of standing in a fiting room and trying things on and saying, “How does this look?” I think maybe that experience is a little bit intimidating. When we’re choosing who to put it on in the catalog and even how to put it together, there’s always a piece of accessibility that’s really, really important. We try not to be too intimidating because that will turn a guy off. So when you ask if there are any mistakes, I think it’s that: the guy says, or his wife says, “It has to be this,” or, “It has to be that.” It’s easier for women to see something new and try it out. It’s not as natural for a guy to do so.

Cary: Do you have any personal experiences of having a woman shop for you and not seeing eye to eye?

Jack: My wife is a designer so I know better than to shop for her because she definitely has an opinion and a point of view. It’s not even worth it. And the same goes this way. If she’s on a shopping trip in London and she sees a vintage Barbour or something, she’ll pick something like that up for me, but she’s not going to pick up a pair of jeans or a suit or even a suit jacket or blazer. But I think that’s rare. I think that’s a unique thing because we both live in this world. I know my sister, for example, will try to buy something for her husband, and it’s not always so well-received.

I think that’s general. If it’s not in the guy’s comfort zone, if the woman is trying to buy something for the guy that he wasn’t going to buy himself, it gets tricky. And I wish it wasn’t that way. I guess that’s the idea of the service we have now – Jack Knows Best – it makes it easier for guys to try new things out.

Cary: So do you think as a rule it’s better for a woman to not shop for a man?

Jack: No, but I think it’s better if he’s with you. And I think guys get turned off by pretension. Any retail or “fashion” that lives in that world can turn a guy off.

Shawn Buchanan: Shopping can be very overwhelming, which is great about what [Jack] does and what’s done in the store. It’s really well-edited and focused, and a guy needs that sort of focus. If it’s too all over the place, where a guy can buy all these different brands, it’s overwhelming. What Jack is doing is so great because it makes it so much easier. And it’s aspirational. This is what a guy wants to look like. And maybe he is used to wearing these wider, crazier, boot-cut pants, but then you say, “Look at this picture of yourself years ago at this party, and look at yourself now. You look great.” And I think that’s what Jack has been able to bring to the table and why this has been such a successful moment for J. Crew and the men’s shop.

Jack: And I think it’s an evolution too. It’s not telling a guy he needs to throw out everything striped and replace it with something polka dot. It’s not a complete contrast. It’s just changing proportions a little bit. The jeans got a little bit slimmer at the ankle. The notch on the lapel is a little bit higher than it was five years ago. What you were saying about seeing the photo from the party five years ago – just little bits like that go a long way for guys.

Cary: In the men’s shop or in the Liquor Store, do you see more men shopping for themselves or men shopping with women?

Jack: I was in the men’s shop last night and it was loaded with guys. Guys shopping alone, guys with friends. A few of these guys seemed to be from out of town. New York is sometimes a tricky thing because life is different here. It’s not the rest of the country. But I’m seeing more and more guys shop alone without a girl present. That’s definitely a J. Crew thing though – especially because it’s a name they’ve known for a long time. It’s not a designer that just came out two years ago. It’s nice that we can be a trusted editor to show these guys how to pair it down. As Shawn said, it’s not overwhelming. It’s nice that we can say, “This is the jean. This is the jacket. This is the shoe.” You don’t have to choose from too much.

Shawn: But it’s also a good education for women too because looking in the catalog, you can see, for example, that the pant doesn’t have to sag in the seat. It’s more of a subliminal message. People are seeing this, and whether the guy is in a suit, and he’s a Wall Street guy, or whether he’s a downtown guy in a band, they can all wear these clothes based on what Jack has brought together.

Cary: What advice would you give a woman in, for example, the Midwest, who is shopping for her husband or boyfriend, that might be unique to basically anywhere but New York? Men here are more courageous about trying new things and being more on trend. And men in Missouri or Alabama are just more conservative.

Jack: Well I think the most important thing is to start with something that fits perfectly. Don’t worry about having it in five colors. Let’s say this woman in Missouri wants to take her husband shopping for a new jacket. Just get one perfect gray flannel blazer. Something he can wear twice a week and get used to that new fit. That way he doesn’t feel like he has to buy three colors of the same jacket and feel obligated to wear it all the time and then grow spiteful. It’s nice to just ease into it. Buy one perfect jacket and wear it a couple times a week, and he kind of gets used to how things should be fitting. And after a while people start to associate him with that jacket. “Oh, there’s that jacket that you look so great in.” It’s positive reinforcement. Someone says, “I like the way that fits.” If you hear that a couple times a day, after a couple of weeks, a couple of months, you start to build a confidence. And I know in [the Midwest] guys don’t want to look metrosexual. They won’t feel like they care too much; they just know that, “Wow, people notice when I wear this jacket.” But it has to be a gradual thing because if you shove it in a guy’s face, he’ll turn off pretty easily.

Cary: It’s interesting that you mention the metrosexual trend.

Jack: I know. And it’s so dated.

Cary: It is so dated, but it’s still alive and kicking in smaller cities. I think that a lot of men fear that if they want to be fashionable, that’s the route they have to take.

Jack: Totally. It’s a little more black and white. If you’re this way, you don’t think about clothes. And if you do think about clothes, you must be this way. Maybe it just takes time for everyone else to get there. But you’re absolutely right. It’s dated but it’s still there.

Cary: What would be some fail-safe options for a girl if she wants to surprise a man with an accessory or a shirt? Where would you say she starts if she doesn’t want to take him shopping?

Jack: It’s a good idea if she doesn’t jump intervals. If her husband is into baggy jeans, she shouldn’t jump into super slim, skinny jean. Take steps there. If he’s a boot-fit guy, go to a straight fit. He’ll notice, of course, but it’s not a drastic contrast. The other thing that you see out there that a lot of guys don’t get is a really great suit – and you see this in New York all the time. You see it on the subway in the morning – the guy’s suit fits great. It’s updated and contemporary, and he is wearing the worst shoes. He’s like, “Well, they’re not sneakers. They must be dress shoes.” A great thing for any guy is a nice pair of Alden wingtips. And with Alden, there’s a whole range. It doesn’t have to be a $600 cordovan wingtip. But just a good sturdy classic shoe that a guy can wear with jeans, to work or on the weekend, or he can wear it with a suit five days a week. That’s something that a woman is not going to regret purchasing. That is perfect for a guy. Of course, you have to get his size right.

Cary: And what tips would you give for women who have a great guy with terrible style? How would you suggest that she launch a full makeover?

Jack: You just definitely do not want to humiliate. You don’t want to make him feel like he’s on one of those reality shows where they open his closet and just start making fun of him. That’s got to be the worst. Keep that in mind, and just try to stay on the other end of that. I guess the biggest part of that that is really jarring is the element of surprise.

Shawn: As Jack was saying, it’s an evolution. If you’re used to square-toed shoes, you go to a wingtip that’s not as square. It’s classic. It will last you a lifetime, and you can wear it whether you’re twenty years old or you’re a hundred years old. And it’s like the jacket, an evolution. It’s a grooming thing. It’s changing little things slowly.

Jack: Take pleats. It took a long time for pleats to finally go, so it’s got to be gradual. And the more classic, the better. Look at a picture from the early ‘Sixties – you can always gauge it on that. If you’re about to spend a lot of money on your husband, it’s always good to check with history first before you try something really tricky. There’s sort of a sweet spot in the middle and then on one end there’s the guy who doesn’t care and looks like he doesn’t care, but then there’s also the guy who cares too much. And he’s always trying the latest trick, wearing non-functional clothes. You see these peacocky guys too, and they’re both just as far on the spectrum from the sweet spot. And those two guys are totally afraid of each other – the guy over here who’s always wearing the most experimental thing is always freaked out by the guy who doesn’t care, and vice versa. There’s something about history and functional clothing. If you can look at something that has a purpose, that means that it’s classic, and it isn’t going to look tired in two or five years.

Cary: Men and women shop very differently. Do you think that those differences affect what they buy for themselves? In other words should a woman think and shop like a man to buy for a man?

Jack: Women are definitely hunters. They’ll see something in a magazine or on a website or on a celebrity, and they’ll look at the credit, and they will absolutely find it. A guy could walk into a store, and if he’s not so sure of himself and he doesn’t see what he’s looking for, or they don’t have his size, he could walk out and it will be another year before he goes shopping again. But I do think that if a woman is shopping for a guy, she already has an idea of what she’s looking for. She saw a picture of a suit or a sweater, and she’ll certainly find it. I don’t think she has to shop like a guy to buy for a guy. I think she’d be handicapping herself.

Cary: I know some men who do hunt, and they won’t buy anything else until they find it.

Jack: That’s a unique guy. That’s the guy who’s probably reading Selectism. And he’s hopefully the guy who’s at our Liquor Store and the men’s shop. The involved guy who’s paying attention but not too much attention and knows a good thing when he’s sees it. That guy is definitely there.

Cary: So the guy who reads Selectism, who’s already educated in what he wants and what is trendy and the brands that he’s interested in, that presents a different challenge for his wife or girlfriend.

Jack: Yeah, I wonder if that wife or girlfriend is even shopping for him. She probably doesn’t see him as a project. I think there are definitely women who, for example, find the perfect guy, but he dresses like that. I think a lot of women see that as a challenge. It’s kind of sweet, isn’t it?

Shawn: He’s a keeper. A fixer-upper.

Cary: Often that girlfriend will clean that guy up for the next girlfriend.

Jack: It’s like real estate.

Cary: I’ve been shopping with a man who walked into a store and immediately knew he wouldn’t like anything there, which I couldn’t believe, and then later in the same day filled up his shopping cart in the same online store.

Jack: I think a lot of guys don’t want to seem like they care too much. They can feel vulnerable. But if you do it online, you can do it privately, and you’re not letting your guard down for anyone. You’re not browsing the dorkiest thing in the store and worrying that everyone else is looking. I say “dorky” to mean whatever he picks up and thinks, “Oh, should I even be looking at this? Is it the wrong fit?” But that’s a good point.

Cary: Some guys have great style, but they just don’t like to shop.

Jack: A lot of guys just want to get in, get out, and get it over with. And other guys just enjoy it. I guess I’m one of those guys. Last night I was in the men’s shop on Broadway, and the place was loaded with guys really looking for stuff, trying things on, asking a lot of questions. But a lot of guys won’t ask questions. If they don’t see it in their size, they’ll walk right out. I think guys are getting somewhere. And it’s not just those really fashiony guys anymore. It used to be those polar opposites, but now there’s something in the middle, and it’s only happened in the last few years.

Shawn: One thing that men do get help with, from their girlfriends, is the suit. What J. Crew has been able to do with the cut and the fit now takes so little tailoring so I think that’s an interesting area because it’s still an area where, unless a guy is in the business, he still doesn’t know how suiting works. A girl is more in touch with that.

Jack: I think it’s good any time you’re buying a suit to have someone with you whose eye you trust. Even if your girlfriend’s not around, get a good friend to have a look at it. You can only get so much from a mirror, and the guy in the store wants to sell you a suit. It’s good to have someone to tell you if it’s too big in the shoulders, up a size or wherever. Someone you trust. We have two fits now, and one of them is the Ludlow, which is definitely more downtown. It’s slimmer, more like a ‘Sixties silhouette with a more narrow lapel. And then there’s the Aldridge, which is a great fitting suit, but it’s more classic. Not as narrow. Not that one is conservative, and one is flashy. A bigger guy with bigger shoulders will wear the Aldridge. If you have a broader jaw, this has a wider lapel. A more muscular, more athletic guy will wear an Aldridge. So we’ve really separated it into two camps to not make the bigger guy feel like he’s trying to squeeze himself into a little suit. I always had a hard time buying suits because I looked like I was trying to wear my dad’s suit, a hand-me-down. Now it’s nice to have something with a narrow lapel and a slimmer leg, and it doesn’t cost three grand. That definitely helps because it makes both guys feel confident about what they wear.

CRF: Men’s trends turn over much more slowly.

Jack: Yes, and they’re not reinventions. They’re just evolutions. It’s always been a suit; it’s just about how it fits and what it’s made of and whether it has two vents or one vent, three buttons or two buttons, they’re all just variations of a classic. That’s why I think it takes guys a lot longer to update their closet because they think, “I’ve already got a suit. Why do I need another suit? I got this suit ten years ago, and it fits me fine.” I think that’s part of it. If you’re not paying attention to those details, you’re not going to get it. It’s not like a car. You look at a Honda from 1994 next to a Honda from 2004, you can look at it and know that one is the newer car. I don’t think guys get that. That’s why it’s good to have someone – a girlfriend or someone you trust – if shopping isn’t your thing.

CRF: What is your last word for a woman as she prepares to shop for or with her guy?

Jack: I think it’s really important to remember that she’s not going to get far if he feels blind-sided. If he feels sabotaged at all, like, “Oh my God, she threw out everything in my closet and replaced it with all this new stuff that I’ve never seen before.” You’ve got to involve him and make him feel like he has the same input, even if he doesn’t.

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