In our advice column, Ask the Strategist, we take your most burning shopping questions and survey friends, call up experts, and draw on our own personal experience to answer them. As always, please comment with any questions of your own — we’re here to help.
Question: My boyfriend is in his late 20s and stuck wearing band T-shirts. A lot of the clothes he likes are a little immature, and the emo kid in him thinks a lot of men’s fashion is too square or boring. We live in the Pacific Northwest, so even “formal” isn’t too formal, and he works in the cannabis industry. Do you have recommendations for things that can help make his wardrobe more age-appropriate?
The biggest take-away from Netflix’s Queer Eye is that most people don’t actually need a full makeover. What they need is a confidence boost and a little push. In the style department that means finding clothes that fit well and allow a person’s character to come through. Your boyfriend’s clearly got plenty of fashion opinions, but it seems like he’s lacking the tools (enthusiasm, courage?) to evolve his wardrobe from emo-kid to emo-loving-adult. To be clear, we have nothing against band tees. Even the most destroyed vintage T-shirt can look stylish and grown-up as long as it’s counter-balanced by less tattered basics. He works in the cannabis industry which leads me to believe he doesn’t necessarily need to dress up for his job, but he can still kick it up a little.
To help him out, we talked to professional stylists Donnell Baldwin and Melissa Buck about fashionable basics that will instantly transfigure his closet. Buck recommends starting the process with a some homework: “I’ve learned the best way to get a guy onboard is by first giving him homework. I ask them to keep a folder on their phone or actually create a private Pinterest page of outfits or clothing that they like.” This way she gets a visual sense of what a client is into before shopping. Buck has also found success by setting realistic expectations, taking into account her clients’ tolerance for trying on clothes. “I find that most guys don’t really like the hunt (shopping) like some of us do. They get really annoyed by around the fifth-to-seventh-garment mark.” Here’s a brief starter guide to revamping your boyfriend’s closet.
Both Baldwin and Buck recommended starting with a dark pair of jeans. Baldwin says, “If he has torn and tattered jeans, I would get a pair of dark-wash selvage jeans. If you don’t want to wear a trouser, sometimes you can get away with a crisp white shirt, a dark jean, and a proper brogue. So I would say elevate the jeans a bit.”
If he’s on a budget, Uniqlo is a great place to start, and a pair of black jeans can make wearing band tees even easier. The added stretch makes these jeans super comfortable from day one. “Uniqlo typically has pants with a little bit of stretch to them, which is perfect if you’ve got thighs or a butt,” says Baldwin.
Buck considers “a great oxford white button-down shirt for work that can also double as a cool going-out shirt with jeans” a wardrobe must-have. Because he might wear it several days a week, she says it’s worth investing in a higher-quality option, if possible: “Spending a bit more on this particular item really pays off.”
For men who are still getting used to the feel of a “dress” shirt, this shirt, which is woven loosely and prewashed for natural elasticity, would make a great first step.
“I think white shirts are classic and clean. They always look good, so I guess that’s kind of like 1B. But 1A would be a denim shirt that you can dress up or throw on with a navy blazer and your dark jeans.” says Baldwin, who loves to layer his own denim shirts over a more casual tee. “If I’m wearing my favorite concert tee that I’ve had for 15 years, and I’m in a meeting, it’s under the denim shirt so no one sees it. But as soon as I leave that meeting I take off my tie, unbutton the shirt, show a little bit of the concert tee, and now I’m super casual.”
According to both Buck and Baldwin, an easy way to add some grown-up style to any wardrobe is by adding a classic navy blazer. “I always had a navy blazer just in case someone called an impromptu meeting. You know you can just throw the navy blazer on and you’re ready,” Baldwin says. And to get the most bang for your buck, look for one in a lightweight, all-season wool.
Blazers aren’t for everyone. But you can get a similar, yet slightly more casual effect with a navy chore jacket like this one from Everlane. It’s also a great option for men with less cash to spend.
A lightweight bomber jacket will also instantly dress up jeans and a T-shirt, and is a nice option for shorter men, too.
In addition to a blazer, Buck stressed the importance of a “good, go-to cool lightweight jacket, whether it’s an army-style jacket, denim, or a black or brown leather bomber.” Since this guy lives in the Pacific Northwest, we’re recommending outerwear to combat the rain. This Filson jacket is waterproof and will look good with literally anything he’s got in his closet.
Baldwin also mentioned investing in a great piece of outerwear. “The other thing I would say is a staple is a great outerwear piece. Especially in the cooler months, if you’re having a meeting and it’s quick, you’re probably not going to take off your jacket or your coat. So the very first thing people see is that strong outerwear piece.” This neutral Mac coat from Topman has a nice silhouette.
And if he doesn’t have a raincoat, this olive green, rubber-coated raincoat is a perfect mix of style and function.
Guys have strong feelings about their shoes. So we’re talking about a few different kinds. Firstly, Baldwin recommended chukka boots for their versatility. “They’re classic, they just seem to go with everything and they really stand the test of time. There’s not much that I feel they don’t go with, except a suit. Wear them with jeans or a pair of chinos rolled up to show a little bit more of the boot.”
Another go-with-anything classic brand is Doc Martens. We like black oxford shoes that look like a dress shoe but still feel casual.
But, if he’s looking for something more casual, you can’t go wrong with a classic sneaker, like monochrome Chucks. “Converse sneakers have been cool for God knows how long, and depending on the type you get, they just still work,” says Baldwin. “I literally just recommended them to an acting buddy of mine whose show is opening up in a week. They’re clean, they’re classic, no one will think twice about it.”
The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.