If you’re going to give shopping with your guy a real go, you’re going to have to be savvy about it. No impromptu trips to the mall. This is serious. And if you want to make it a productive and enjoyable experience for both of you, you're going to need a strategy.
1. Be respectful of his tastes.
Even guys who say they know nothing about fashion and don’t care what they wear can still feel hurt if you tell them everything they own is crap.
Ask your guy to show you his favorite clothes. Find out why he likes them — the color, the print, the way they feel, etc. Don’t let him get away with “Uh… I don’t know. They’re just cool.” You need to know what he values in order to figure out how best to help him and he needs to feel comfortable in whatever he's buying so that he actually wears it.
2. Make a shopping list.
Go through his wardrobe with him to figure out where the holes are before you go shopping. Without a list of specific items to look for, your guy is just going to gravitate toward the same stuff he always buys. You don't have to necessarily stick to the list or get everything on it, but it's good to have.
3. Limit yourself to a couple stores.
If your guy isn’t really into shopping, dragging him to a bunch of stores isn’t going to help things. Instead, pick a couple good places and just focus there. Try to make them places he doesn't usually shop so that he is less likely to fall into old habits and make sure you stop after two or three stores tops, especially if you find good stuff. It's always best to end on a high note, and if he walks away feeling good about the experience, he'll be more likely to want to repeat it.
4. Choose stores where he can't f*ck up.
It's really hard to go wrong at a place like J.Crew or Club Monaco, so your guy can just go wild and grab whatever he’s responding to. Onassis and Saturdays Surf NYC are also solid options whether you’re shopping in-store or online. And Bonobos and Frank & Oak are two of the best online menswear retailers around.
From left to right: J.CREW; CLUB MONACO
Clockwise from the left: Red Shirt With Black Stripes, SATURDAYS; Navy and White Striped Button-Down, BONOBOS; Red Puffy Vest, FRANK & OAK; Navy Canvas Backpack, FRANK & OAK; Olive Jeans, ONASSIS CLOTHING
5. Make a list of fashion deal-breakers.?
Some guys don’t realize that one tiny design detail can take a piece of clothing from totally great to totally awful, so it’s a good idea to talk about what to avoid before you go shopping. If they’re things he loves or wears a lot, be gentle, explain why it isn’t working, and offer alternative suggestions. Keep the list short, though — two to three things at most. If you're too negative, it will set a bad tone.
6. Don’t shop for yourself.
Everyone likes attention. He’ll be more invested if you make it all about him.
7. Pick your battles.
Use your influence when he’s on the fence about a piece you love, but if he absolutely hates something, don’t try to force it on him. The more you fight him, the more reluctant he’s going to be to keep going. If you both like something but it’s too expensive, offer to pay for half. Even if he doesn't take you up on it, he'll be touched that you offered.
8. Don't expect a complete transformation.
Even if you want to, you're not going to be able to change his look entirely in one shopping trip. Think of it less as a makeover and more as a style upgrade. If there are specific pieces of his that you absolutely hate, keep an eye out for similar things that could replace them and encourage him by saying something like "I love this on you. It's sort of like your _____, but I actually think it's much nicer." Then explain why — the buttons are nicer, it's more versatile, it fits better. A lot of guys respond to reason and logic, so use that to sell him.
Do you have a question for Cosmopolitan.com's Style Editor, Charles Manning? Submit it here or tweet him @charlesemanning. Happy dressing!
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