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How to Update Your Millennial Style

Three simple tweaks to modernize your wardrobe.

By Madeleine Kim

The most surprising thing about aging is how much I’ve enjoyed it. I turned 30 last year (which, I know, is still young by most standards), and where I’d always expected to mourn the end of my 20s, I instead found a new feeling of confidence and a sense of possibility. It turns out, I like not being the youngest person in the room; I find it liberating to know I’m no longer part of the most discussed demographic.

That said, I don’t want my generation to dictate my style. And while I’d like to believe that my fashion sense comes from some innate creative place deep within, well, that’s just not how it works. As New York Times fashion critic Vanessa Friedman wrote in a recent edition of her “Ask Vanessa” column, “our style is often formed by the ethos of the time in which we came of age, started buying our own clothes, and had to figure out what it meant to navigate identity in the outside world.” 

If you’re a Millennial like me, and you came of age during a time when the jeans were as tight as hot dog casings, you may feel like the clothes you gravitate toward today feel dated. This does not (I repeat, does not!) mean you need to toss out your entire wardrobe in favor of low-rise cargo pants and crop tops. Please don’t do that. But there are a few easy tweaks that will make your outfits look more current, without being overly trendy or feeling like you’re trying too hard. Below, learn how to update three quintessentially “Millennial” pieces.

Skinny Jeans

If you’re ready to replace your skinny jeans…

Try a straight-leg silhouette, like the Daria jean, which I’m wearing here in black. This pant is fitted through the waist, hips, and butt, but relaxed and easy through the legs. The Daria shows that you don’t have to step too far outside your skinny-jean comfort zone to find a style that feels current. Here are three ways I styled it:

  1. With the knit Crimmins top, vegan leather Sierra shacket, and vintage Louis Vuitton loafers (similar: Grace loafers) for a comfortable, ’90s-inspired day-to-night outfit.
  2. With the black-and-white Leslie T-shirt and the Ness jacket, which is like the updated, much chicer version of the J.Crew military jacket that was inescapable in the late 2000s. I wore it with Havaianas flip-flops for a springy look, but sneakers or boots would also work well.
  3. With the Jett tank, plus the plaid Lacie top, only buttoned in the middle (you could also try this outfit without the tank underneath if you’re not wearing it to work). With Doc Marten Chelsea boots, the plaid takes on a slightly alt-kid energy, which feels so right in my Millennial soul.
If you want to keep wearing your skinny jeans…

Take cues from Jessica Camerata of style blog An Indigo Day, who provides weekly styling tips for Millennials on her blog and Instagram. “My favorite way to make my skinny jeans feel updated is to pair them with more oversized pieces on top,” says Jessica. She recommends topping your skinny jeans with an oversized button-down and draping a sweater over your shoulders. “Gone are the days of wearing tight with tight, so the looser you can go on top, the better to refresh this beloved silhouette,” she says. For shoes, Jessica suggests “a trendy style like a mesh ballet flat, platform loafer, or sneaker.”

Fitted Blazers

If you’re ready to replace your fitted blazer…

Try a belted blazer, like the Twidwell, which provides the same waist emphasis and structured look as a fitted jacket, but feels more sophisticated. I’ve found the cool charcoal shade to be quite versatile (although I’m also lusting after light orchid…). A few ways to style it:

  1. With the cardinal red Jett tank, the tusk Milo jeans, and patent leather loafers. I wasn’t sure if the cool charcoal and tusk shades would pair well, but when I tried them on together, I found that it really works—especially if you incorporate a pop of red. I also love how the longer length of the Twidwell jacket makes the Milos look more like trousers than jeans.
  2. With light-wash denim jeans and dainty white shoes. I included this look to show how much range the Twidwell jacket has. The hyper-casual feel of the jeans creates such a contrast with the ultra-structured blazer, and the bright white shoes make the outfit feel dressed-up without reading as corporate.
  3. With the Horton pants, a ribbed tank from Aritzia (sold out in this color but available in pearl), and the Lana boots. I like this look for a lot of reasons, one of them being that I’ve never looked taller in my life. The Twidwell can read as a true power piece when you want it to, and in this look, that room-commanding vibe is on full display.
If you want to keep wearing your fitted blazer…

“If you invested in a great form-fitting blazer that you’re just not ready to get rid of, try pairing it with a wide-leg trouser like the Milo or a straight-leg jean like the Daria,” says Jessica. She also suggests experimenting with looser, more casual underpinnings, like T-shirts, and adding visual interest by draping a sweater over your shoulders. “The Kim sweater in dot print is a favorite and adds a nice layer and texture to the look,” Jessica says. (See more on how Jessica styles blazers here.)

Ankle Booties

If you’re ready to replace your ankle booties…

Go for a pair that’s sophisticated but comfortable, like the knit Lana boots, which feature tons of hidden support in the footbed. And don’t forget to think about styling: Wearing ankle boots with an above-the-knee dress or skirt may be making your outfit look dated. Instead, try a longer hemline, like the Marlowe skirt, which combines a timeless elegance with a modern pattern. Here are a few ways I styled the Marlowe skirt and Lana boots:

  1. With the easy-to-tuck Jett tank and the Kiki sweater draped over my shoulders. The Kiki adds a beautiful burst of color, and I love how its chunky cable stitch contrasts with the plaid of the skirt.
  2. That same outfit, but with the Kiki tied around my waist instead. Black and white go with everything, so you could accomplish either of these looks with any colorful sweater you have at home.
  3. With a black V-neck knit tank top that’s similar to the Peggy and a cropped cardigan I got secondhand (this one from Akris Punto is similar). To make this look more office-ready, replace the cardigan with a cropped jardigan.
If you want to keep wearing your ankle booties…

Jessica and I agree that you don’t have to send your favorite ankle boots off into the sunset—but may want to rethink how you’re styling them. “Gone are the days of pairing ankle boots with a skinny jean and a smidge of skin,” Jessica explains. “Instead, pair those old-school ankle booties with your long, wide-leg pants and let the toe peep out.” Wondering where to start? Go for the Horton pants, Milo jeans, or Bia pants.

Written By

Madeleine Kim

Madeleine Kim is the Senior Brand Manager at M.M.LaFleur, where she started out as a stylist. She loves developing styling-focused content and creating newsletters that bring the M.M. community together.

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