“I think it’s pretty cool that these companies are trying to recreate working with a stylist, but I don’t think they understand the true value of it,” said Lauren Messiah, a professional stylist in Los Angeles. “What I do for women as a personal stylist, a lot of it isn’t even about the clothes.”
Professional stylists often discuss goals, priorities and other issues in order to develop a client’s personal style. It’s a long process that can take months of working one on one with someone.
“Working with a stylist is more about figuring out who you are, and then dressing yourself accordingly,” Ms. Messiah added. “You really get to understand how things are supposed to fit so you can maximize its use in your closet.”
Don’t expect to get the same level of service in a box, Ms. Messiah says. She suggests having specific action items ready for your online stylist because, unlike an in-person stylist, they won’t ask you questions about your priorities and goals. It’s crucial to have an idea of what you want beforehand. Instead of “I want a better wardrobe,” you might tell your stylist, “I need nicer dresses to wear to company cocktail parties” or “I need casual clothes that also look professional for my remote job.”
As long as you keep your expectations realistic, however, these services can be useful, and there are a number of ways to ensure you have the best possible experience with them.
Pick the right box to start
There are two different categories of clothing box services: subscription-only and try-and-buy. Subscription-only services, like Threads Monthly or Five Four Club, don’t send clothes that are intended to be sent back. (In fact, some don’t even offer refunds.) These subscription boxes work just like Birchbox or Blue Apron: you sign up for a box and keep what you get.
By comparison, Stitch Fix and Trunk Club are try-and-buy services, meaning you try on the clothes and only buy the items you keep. You can order a box regularly and set up your own subscription, but they’re ultimately designed to allow you to try on clothes in the comfort of your home. This also means you need to trust yourself to reliably send back the items that don’t fit or that you don’t like.
If you know what kind of clothing you like and simply want a regular shipment of new threads every month, subscription-only services are probably your best bet. However, if you’re looking to try new styles, address specific clothing needs for your body, or just need the help of a professional to pick out pieces, you’ll probably want to stick with the flexibility of try-and-buy.
Our favorite pick, Stitch Fix, offers that flexibility. It also offers a variety of sizing, from petite to tall to plus-size, which is another factor you want to consider when picking the right box. Most, but not all, boxes have clothes that fit a variety of body types, and you can typically find this information in the FAQ section of their website. For more on what made Stitch Fix the winning choice — and for details on other options — check out our full comparison and test at Wirecutter, a New York Times company.
Give your stylist specific feedback
Once you sign up for a service, take the time to fill out your profile thoroughly. Stitch Fix and Bombfell, two of the most popular options, take you through a series of detailed questions about your measurements and preferences.
This can be time-consuming, but the more time you spend offering accurate answers, the better chance you have of getting a box you like. With Trunk Club, another popular option, you’ll answer a few basic questions, too, but then a stylist will contact you, either via email or chat, to get more insight and feedback from you.
“I would take the time because that really informs what you’re getting,” said Jon Shanahan of the YouTube style channel The Kavalier. “When I first used Trunk Club, I just wrote a couple of things to my stylist, and looking back it wasn’t very helpful. If you take the time to say why things fit what you like, it’s in their best interest to get you right as a customer.”
Mr. Shanahan even suggests getting feedback about your style from friends and family to help you with the process. Many of these services also include a section where you can leave a message for your stylist. Don’t leave that field blank. Give your stylist as much information as possible so they know what to work with.
If you want specific items in your wardrobe, let them know. If you have specific goals for your style, like more clothes for networking events, tell them. Search for some styles you like on Pinterest, pin them to a board, and send the link to your stylist. Most services will directly ask for a Pinterest board link.
Learn some style basics
It doesn’t hurt to learn the basics of personal style, either. This way, you know you’re requesting the right types of clothing, and clothing that you like and that looks good on you.
“I think there’s something fundamentally wrong with how we think about style. “You don’t know why you’re wearing something, so it just ends up being another thing in the back of your closet. Get to the reasons why you want something,” Ms. Messiah suggested.
Personal styling is often a self-discovery process that explores your desires beyond the clothing. The process helps you determine why you want to look better in the first place, and then encourages you to align your personal goals, career goals, and even relationship goals with your style. If you want to excel in your corporate career, for example, you’ll do well to focus on choosing professional clothing that supports that goal. That means leaving out shorts and T-shirts when you place your order.
Try a second box
Your online stylist might not get it right the first time around. “You need to give it two cycles for them to really nail everything,” Mr. Shanahan added. “That’s when you really start to say, ‘Yes you got this.’”
The idea is that the more you work with your stylist, the better a grasp they’ll have on what you’re looking for, specifically. In fact, when you send items back, most services allow you to briefly explain why you’re sending that particular item back. Maybe the shoulders are too big or you just have too many of that type of item in your wardrobe already. Your stylist will see these notes and know not to send you similar pieces next time.
Thus at $20 to $25 a box, it may be worth a second or third chance if you’re unhappy with the first box. And some boxes, like Bombfell, don’t have a styling fee at all. As Mr. Shanahan put it, “You might as well give it a couple of shots because there’s a very low barrier to entry.”
Finally, it’s worth noting that shopping for clothing can also be a stressful experience, namely when you don’t find anything that fits you quite right. Try to have fun, and remember to exercise some self-compassion along the way.
“It’s not you, it’s the clothes,” Ms. Messiah said. “There’s vanity sizing. No one designs the clothes with you in mind.” She advises her own clients to keep an open mind when it comes to trying on new things and remember: “it’s all part of a journey, but at the end of the day, it’s just clothes.”