I Got the Madewell Styling Treatment

Emily Newnam, the brand's style director, answered all my questions.

Mar 08, 2025

This letter is free thanks to Madewell.

I love watching stylists at work. They’re tuned in to details that others aren’t and are hyper-focused on tailoring and fit. The slightest adjustment to a hem, a sleeve, or a tuck can make a huge difference that the general public might not even notice. But, as I’ve written about before, stylists are responsible for how we dress—they’re the reason everyone is suddenly so obsessed with bootcut flare jeans and ‘Old Hollywood’ glamour on the red carpet. They are translators and trend doulas, taking big, high-fashion ideas and communicating them to the masses. And they’re not just for celebrities—we have access to them, too. Earlier this year, Madewell approached me about working together on a newsletter, and I learned that they have an in-store styling service, which I thought Shop Rat readers might be interested in learning more about. On the brand’s website, you can easily book a one-on-one appointment, and someone at the store will fill your dressing room with suggested styles, talk through what you’re looking for in terms of fit, pin your hems, and send your denim out to be tailored for free.

The program, which everyone should take advantage of, is overseen by Madewell’s style director, Emily Newnam, who connects the brand’s editorial styling back to the work done in stores. To better understand what an appointment might look like, I visited the Madewell office last week to try on the new March collection and have it styled by Emily personally and tailored to my preferences.

Getting the full Madewell styling treatment with Emily and the brand’s favorite tailor, Wes Nault, who told me it’s best to pin the backs of pants first.

What a treat! I also used it as an opportunity to ask Emily a bunch of styling questions, some of which readers submitted via the Shop Rat chat. Below is a condensed version of our conversation. I hope you find it as helpful as I did!

I just learned about Madewell’s in-store styling program. Can you tell me more about it and your goals for it?

Our goal is to convey to the store stylists what we're discussing here [at the office] with the creative and design teams so that there's synergy and nuance to their conversations with customers in person. Once a month, I’ll create videos and a visual guide around our new denim styles to share with them. The program focuses on fit. Our store stylists are trained to help you discover what works best for you and your body. It’s a conversation. They’ll ask you questions like, where do you want your jeans to sit on your hips? What proportions do you prefer? What type of shoes will you wear with them? Once you find the right fit, they’ll pin your hems and suggest minor adjustments, and then your garment is sent out to a tailoring service. It's complimentary because we really want to get you into your perfect pair.

A styling service sounds like something that only fancy people partake in; it’s great that it’s available to everyone.

Denim can bring up so many emotions, especially when you're alone in a fitting room. If you can’t find the right fit, you’ll just want to give up and leave the store. But if you can have a personal dialogue with someone, you might not feel as discouraged and stick around. The program is also a great way for us to get feedback. I want to know what customers like, what they're asking, and what we have to solve.

Can you walk me through a typical in-store styling appointment?

There are two typical scenarios: Either someone sees something online that they want to try on and possibly have tailored, or they have no idea where to begin. If someone is unsure where to start but has tried something on before, our store stylists can access their profile and see what has fit them in the past. If they really loved the Superwide or the Rail Straight, for instance, those are key styles that we continue to refine, so I would recommend an updated fit or wash in a style they've worn before. Once we find something they’re truly comfortable with, we can discuss new trends in the market, like the horseshoe trend, which we have, but our Barrel Leg is a bit more subtle. The stylist will pull some shoes, belts, jackets, and other pieces, but we prefer to start with the denim first to get them to a place where they feel excited and then add on. Without that first layer of confidence, the rest doesn’t matter.

Do you do styling appointments for menswear as well?

Yeah, for sure. We often find that couples come in and go on that journey together. Personally, I like to wear our men's pieces, too, especially our sweaters. For March, we’re introducing a wider-leg fit for men. Our customers may not want to look like a Dimes Square baggy jeans guy, but they still want to feel a little bit cooler—they want to branch out from skinny jeans—and this is a more subtle way of doing that.

Do you have any tailoring advice for men?

You don't want your belt to be too functional; it should mostly be decorative. If you need your belt to keep your pants up, bring them to a tailor.

What key womenswear trends should I know about for spring/summer?

I’d say ‘boho’ across different categories. We've gotten so minimal and done ‘uniform dressing’ for so long now that I'm excited to return to feminine, pretty things again. For March, we’re calling it ‘soft utility,’ where there’s a tension between delicate and more utilitarian styles. So we’ve got eyelet details and lightweight pieces, as well as military-style Darted Barrel jeans, baggy jeans with a big cuff, and a pieced panel flare that I’m really excited about. We've also got some really great woven leather belts and bags.

How do you know if a trend is for you or not?

Keep your core, or what you know works, and then play with trends within those constraints. For example, if you want to be like a Chloé girl, I’d wear the flare style with an easy tank top to pare it down and make it more approachable, plus a pointed toe and a low slingback heel to create a bit of shape.

Layering the relaxed carpenter overalls with a V-neck tank, a trench, a woven curve bag, and fisherman sandals.

March is when we start to think about the dreaded ‘transitional dressing.’ Any advice on how to approach that?

I think our new pieces make it easy, like a breathable eyelet blouse and a lace-up sweater. If it's chilly, I would layer with a suede jacket or something that feels more seasonally appropriate. Avoid layers on layers where it feels like you’re suffocating; one element should always feel easy and free. I’m also a big fan of showing some skin—I'm always unbuttoning people's buttons.

If it’s warmer, dressing for the heat in New York can be challenging. I like to layer a short skirt or dress with a layer that hits the same hemline, like an oversized utility jacket, because it looks really considered.

I noticed in the March lookbook that sweaters are tied around the waist, not the neck. Talk to me about that decision.

The Madewell customer is someone who’s not too fussy. Around the neck, it can look too precious or too preppy. There’s no wrong way to do it, but I like it to look like an effortless, tossed-on afterthought.

Wearing the Arc Jean with a matching vest, green slingback flats, and a silver cuff.

How do you navigate big lifestyle changes when it comes to styling? Like when your body changes or nothing in your wardrobe seems to make sense anymore?

My advice is: Give yourself grace. If you've given birth or if your body has gone through changes, denim can be a really scary frontier that you avoid. It's important to know that there are so many different silhouettes out there, so many different fabrications, and different places it can sit to make you feel like it's accentuating your body in the right way. We want the in-store appointments to break that intimidation factor.

Also: Don’t look at the tag. The numbers can mean so much, and we get so attached to them, but there’s no right answer with sizing. I have some of our styles in two different sizes because I want one to sit lower or be more fitted. So, trust whoever's helping you. It can be such an emotional release to let go of the number you think you should be.

There’s also such a fear of being overdressed. How do you combine formal and casual elements?

I would pick one item that feels easy, effortless, and like yourself, and then pair it with something fancier, like a feminine blouse or shoes with a subtle heel. It’s about balance so that you don’t feel like your clothes are wearing you. You also want to have the freedom to move through the day. If you wear a slip skirt, pair it with an oversized sweater. If you’re wearing a mini dress, throw a big jacket over it.

I was recently made aware of the “Millennial tuck,” which I was horrified to discover that I participate in. Can you help me? What do I do??

I am picky about some things, and this is one of them. I think if you're going to tuck in the front, you have to shift the whole silhouette lower. When your pants are too high and tight, and you tuck in the front, the top crumples and sticks out in the back, which is not flattering, especially not from the side profile. But if it all moves down, and your shirt doesn't have much width, it feels a little more effortless. If tucking everything in feels too formal, an alternative is to scrunch your sleeves for a different point of ease.

Wow, I’m so glad we solved the Milennial tuck. That’s huge. Thank you, Emily!