The 10 Style Rules Our Editorial Team Lives By

I’ve loved clothes for as long as I can remember. My mom claims that I started selecting my own outfits at 18 months, and as soon as I could draw, I kept a sketchbook filled with clothing designs. My artistic abilities plateaued at around age 10, so needless to say, becoming a designer was out of the question, but that didn’t stop me from recruiting friends to recreate challenges from Project Runway (enlisting my little brother as a model) or maintaining a fascination with trends.

Over the years, I’ve fallen for many a fad: There was that poncho from Limited Too, the ruffled mini skirt from Abercrombie, a collection of bib necklaces in college—the list goes on and on. Allowing myself (and being fortunate enough) to experiment with a wide range of clothing has helped me hone my personal sense of style, so I don’t have any regrets, but I’m happy to say that I’m now in a place where I think twice about trends before participating in them. My wallet and the Earth are certainly better for it.

To minimize the risk of springing for an item that will be passé before it gets its fair share of wear, I now sit with trends for at least a few months. Take, for instance, pleated trousers and boyfriend blazers, which first re-entered the zeitgeist as streetwear staples a few years ago. At first, all I could see were flashbacks to my mom bemoaning the pleats and shoulder pads of the ’80s. But little by little, these pieces grew on me, and I started to see that oversized styles have a unique ability to imbue your look with chic effortlessness. Now, a pair of pleated pants, a polished T-shirt, an oversized blazer (like the O’Hara or the Yiyan one size up from my usual), and some sneakers is one of my most-worn outfit formulas.

—Emma

This is my most straightforward style rule, but it’s also the one that’s most important to me. There are some pieces that look and feel great when I’m standing stock-still in front of my mirror—but what about when I’m catching the morning flight to NYC and heading straight to the office without changing? Or when I’m squatting down to hug my dog before I leave for dinner? Or when I’m lounging on my friend’s couch chatting late into the night after a champion’s meal of queso and frozen watermelon margaritas?

These non-hypothetical scenarios call for clothes that are stylish, movement-friendly, and comfortable for extended periods. So, before taking the tags off an item, I put it to the test by sitting down, squatting, raising my arms, and walking around my house. To illustrate, see the Rani dress, which is not only beautiful but also one of the most comfortable, flexible dresses I’ve ever put on my body. 

—Maddie

I talk a lot about how minimalist my style is, but it’s all relative. When it comes to shopping, I’m not ascetic by any means, and although I favor neutrals, I love a daring pop of color—key word “pop.” You’ll almost never find me wearing a statement top with a statement pant, and pattern-mixing is a skill I relish theoretically but rarely put into practice. I just prefer to invest in things that are easy to mix and match—things that don’t require much questioning as to whether or not they work with one another.

Similar to my experimenting with trends, through much trial and error, I’ve developed a rule of thumb that keeps me grounded when getting dressed: Commit to one main statement per outfit. This ensures my outfit is neither boring nor busy, and since I have one point of focus, filling in the rest of the look comes naturally. One important point here is that a “statement” means many different things to me: a bright color, a bold pattern, an unusual silhouette, an interesting texture, an extra-luxurious fabric, etc. For example, if I wear a plaid pant, I’m not going to pair it with a red top. (To be clear, that could be a super fun combo—it’s just not me!) Instead, I’ll take cues from the existing palette and go with a white shirt, black shoes, and a black belt. I did say I stick to one main statement, so if I’m feeling more adventurous, I might swap one of my accessories for something a little more unexpected like a sky blue shoe or a flashier belt.

—Emma

Discovering my personal style has been a long process, and it’s still in progress. But one thing I’ve learned is that I feel most stylish and like myself when my outfit includes design elements from both classic womenswear and traditional menswear. I love an elegant silk skirt with a boyfriend blazer; or a slinky dress with square-toe loafers. Fashion should be fun, and experimenting with unexpected pairings is part of what makes it so.

I particularly love pieces that themselves contain multitudes, like the Dolly jacket, which combines structure and sharpness with a single-breasted silhouette and an elegant covered button. Here, I’ve paired it with the vibrant washable silk Vicky tank, the wide-leg Milo jeans, and loafers.

—Maddie

“Trust your gut” applies to clothing, and I’ve learned that the hard way. Every time I ignore my initial instincts about an item that doesn’t have the exact look or fit I’m after, I end up living with regret. I never wear said item enough to justify the purchase, so I’m left with a bigger give-away pile and a guilty conscience. It’s taken me a long time to develop the discipline to walk away from something I love the idea of, but I’ve finally gotten there. Now, when I try something on, if I feel like I’m trying to convince myself that I like it, I know I actually don’t—in its current state, anyway.

Sometimes, it’s a matter of needing to try a different size, and an exchange solves the problem. Other times, the size is overall correct, but the hem or waist needs tweaking. That’s when tailoring comes into play. A word to the wise: Especially when it comes to trousers (like my pictured Horton pants), just assume you’re going to have to alter them in one way or another; when you don’t, just consider it a pleasant surprise. Shopping becomes a lot easier when you normalize tailoring.

Of course, not all items will work out—even after size exchanges or the prospect of tailoring. Growth is realizing that not everything looks good on you, and that’s okay. In the words of Harling Ross Anton, “Opting not to buy something after thoughtful consideration can be just as satisfying as making a purchase.”

—Emma

A fact it took me way too long to discover: You don’t always have to “define your waist.” Nor do you have to like a pair of pants just because they make your legs look longer. Don’t get me wrong—I love a well-styled belt, and I’ve worn many a fitted top tucked into high-waisted pants. But I’ve grown to resist the idea that the most “flattering” outfit is always the best outfit (in fact, I try my best to avoid the word “flattering” altogether). That’s why I usually wear my Merritt jardigan unbelted. Sure, the sash gives me a more “hourglass”-like shape, but I think it looks so much cooler this way.

—Maddie

I’ve come to realize that whenever my outfit feels a little off, it’s probably because it’s reading as soft or as structured, rather than my preferred mix of both. It might be helpful to think of soft styles as those traditionally described as “feminine” and structured styles as those that are more menswear-inspired. However, I try to avoid gendered terminology when it comes to clothing (wear whatever you want, whoever you are!)—hence, soft vs. structured.

Similar to dressing “high-low” (or Power Casual as we call it at M.M.), my compulsion to combine softness with structure is all about balance. You’ll never, ever find me in a floaty top with a full skirt or in a three-piece suit with loafers. Basically, I don’t like to feel like I’m adhering to a theme, which tends to feel costume-like and unnatural to me. For instance, if I want to wear a suit jacket, I might style it with some floaty shorts, a rosy underpinning, and a pair of ballet flats. At its foundation, this outfit is rooted in traditional tailoring, but the leggy silhouette, the delicate footwear, and the addition of cream and red counterbalance the blazer’s business vibe with a bit of romanticism. 

—Emma

As much as I enjoy browsing the runways and staying in the loop on new trends, my biggest source of style inspiration comes from looking to the past. Whether it’s a piece of jewelry that was passed down to me or something I found at a thrift store, I try to incorporate vintage items into my outfits whenever I can. Wearing pieces passed down by members of my family feels particularly special. My denim jacket was my dad’s when he was in middle school. The red and white lucite rings I wear daily were my grandmother’s. I love glancing down at my outfit and thinking about the people who wore those pieces before me.

When I’m on the fence about buying something new, I use my passed-down favorites as a grounding mechanism: Can I pair this new item with go-to vintage styles that have stood the test of time? Something that passed the test recently was M.M.’s kaleidoscope print, which paired so perfectly with my grandmother’s red wool jacket, I felt like it was meant to be. 

—Maddie

In addition to accepting that some things just don’t work on me, I’ve also learned to really lean into the things that do. Doubling or tripling up on something might not feel super exciting in the immediate, but what repeat purchases lack in dopamine hits, they make up for in long-term gratification and low cost per wear (the price of an item, divided by the number of times you’ll wear it). If I’m re-buying something, it’s because I wear it often as a result of it fitting well, looking good, and feeling comfortable.

A few M.M. styles I own in multiples: the Milo jean, the O’Hara blazer, the Horton pant, the Leslie T-shirt, the Paige tank, the Arbus sweater, and the Choe top.

—Emma

Oftentimes, when my outfit feels not-quite-right, it’s because it fits too neatly into one aesthetic. I love a playful splash of gingham, but wearing whimsical patterns and floaty fabrics from head-to-toe makes me feel like I’m playing dress-up. My closet is full of tailored blazers, but you’ll only find me wearing a full-on suit with pumps and a button-down shirt if I decide to make a mid-life pivot and become a lawyer. Instead, I seek out ensembles with a bit of asymmetry: formal pieces paired with casual ones; structured silhouettes with soft fabrics; timeless items with trendier touches.

Dressing this way also helps me get more use out of my pieces. Here, I’ve given a polished outfit I’ve worn to the office—the Leo pullover and Milo jeans—a beachy twist by adding rubber slide sandals and a baseball cap. For a touch of color and an extra bit of elegance, I’ve tied a silk scarf to my straw tote.

—Maddie