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I know we’re all feeling it. Fashion trends come and go, and right now we’re feeling a bit left behind as Millennials. Each generation has their own particular style. But it’s how you update your personal style as the decades pass, that will make you feel on trend without feeling like you’re trying too hard. Sometimes fits need a little updating. I think if you’re still wearing things out of sheer convenience, and not because you love it, you may need an update.

Sure there are some things I think many of us willfully gave up. For me, it was the chevron patterns, the long necklaces that were neon and chunky, the colored, tight-fitting denim and the infinity scarves. And if you haven’t gotten rid of the above, I’ll help show you how to swap them for something that feels not only updated, but elevated.

I’ve been hearing from Indigoers for at least two years now that you are in need of a wardrobe update. You feel stuck in your Millennial ways but don’t know how to update. Updating Millennial outfits doesn’t have to mean a full closet overhaul. Although I would recommend a good KonMari session. Instead, it’s little updates and swaps that can make a big difference. And it’s understanding the new fits and proportions. Lots of balancing oversized pieces with more fitted ones. It’s all about balance. There’s also tons of great inspiration on TikTok. If you need some videos to get inspired too (I plan on creating some soon) check out SketchyMandy and Being Julia. I’ve found their content to be super helpful!

15 Ways To Update Your Basic Millennial Outfit

Before we dive in, I want to remind you of something. Because people tend to have very strong beliefs in their style choices. As we all do (that’s why I started a blog, duh). So you may hate my suggestions. That’s okay. I get it, you love your riding boots from 2012 that you wear over skinny jeans. But I want you to ask yourself when you inevitably feel *seen* in the “we’re not doing this anymore” photo, are you wearing it because you love it and feel good in it? Or are you wearing it because it’s just convenient and still in your closet and it’s become a habit? I’m going to safely assume that many of us are wearing things out of sheer habit.

As we get older we tend to not want to update as much. It’s I think a natural transition as we kind of care less about the trends, and are busy with jobs, life and families. But you’re also important! You should want to feel good and confident in your clothing. So if you feel personally victimized by any of the “no” photos because you’re still wearing it, please ask yourself those questions. If you’re not feeling your best in it, it’s time to update. And to quickly clarify before we dive in, I know we may like all the outfits, but the FIRST photo in each section is a NO, and the second photo is the new updated look, k? Great. Let’s dig into the “dated” to “updated” of updating your basic Millennial outfit pieces.

Update Your Basic Skinny Jeans

I’ll have a BIG post on just this topic as it’s a big one, but you don’t have to toss your skinny jeans. While Gen Z is making us feel bad for them, I promise, we can still hold on to them. Denim is one of those things you wear because it works for you and your body type. So if you want to keep your death grip on them, you can. But just promise me you’ll update them with new styling details like many we’re discussing today. And maybe let’s toss any with lots of rips in them. While distressed denim is popular still, it’s really only happening in the mom jean style.

If you want to swap your skinnies and try something new, I would suggest a straight leg jean that’s tailored. It’s not sloppy nor is it baggy. And they work with your ballet flats, loafers, sandals and cardigans that we also are keeping a death grip on. I really love the Madewell Perfect Vintage jean collection. It’s fitted through the hip and thigh with a straight leg opening. It’s very flattering, super comfortable, and is an Indigoer Favorite. Many of my updated Millennial looks today include jeans from this exact collection.


Update Your Utility Jacket

Oh the security blanket this jacket was for me. The photo on the left is your quintessential 2012 outfit. Low rise jeans (cuffed at the bottom) with white Adidas, a striped tee and a basic utility jacket. Now listen, I love a utility jacket! But we’re updating it. We’re moving to a shacket style, something a bit longer, more oversized. And we’re pairing it with updated denim if we can. You don’t have to, but it helps. This oversized longer line look will work with your skinnies too and you’ll feel instantly updated.


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Update Your Ankle Booties

There are about a dozen different boot options I could’ve pulled as an example here. But let’s just generally say if you haven’t swapped your fashion booties out in about 7 years, it’s probably time. Any cutouts, or super low shaft ankle booties, are probably a no. Let’s go with a slightly higher shaft, which will also work with all those relaxed straight jeans we’re trying, and keep things simple. No crazy frills. I love a Dr Marten boot, a classic Chelsea boot, a pointed-toe ankle boot, and so on. PS read this post on the best boots to wear with all those straight leg jeans so your ankles don’t get cold.


Update Your Blazers

I love a blazer and the best way to update this is to get one that’s slightly oversized. Not too oversized that it swallows you, but a slight boyfriend fit is a really great update to the more fitted, slim styles we used to wear. You can still wear a slim fitted one in your closet if you balance it out with a baggy mom jean on the bottom and a blousey tee underneath. Otherwise, if it’s really snug, I’d probably swap it out. I love a longer lined blazer too. But any relaxed fit, slightly oversized blazer, is a great update. Note the denim swap too above. Skinny to straight leg.


Update Your Jean Jacket

Goodbye are the super fitted, cropped jean jackets. Hello, more relaxed fits. These just instantly make you feel more on trend. I officially tossed my super fitted one for a few updated oversized fits. I also think swapping for a shacket is a great idea too like I did here.


Update Your Riding Boots

I was never into the riding boot trend (the look on the left was a one and done outfit for a giveaway actually). I’ve always been into more fashion-forward boots, or classics. A riding boot, especially in a brown distressed leather like this, is a hard no for me. If you still want a flat knee high boot, I’d opt for a more sleek style in classic black like these. And if you really want a flat boot, try a lug sole one that’s more on trend right now. It’s also about the styling. We’re not wearing htem with skinny jeans, a sweater and a utility jacket. We’re wearing them with maxi dresses, mini dresses, jeans with an oversized boyfriend blazer. You get the idea.

Otherwise, we are wearing real fashion girl boots. Think heels (a low heel if you want comfort) and more elevated silhouettes like pointed toes. Cowboy boots are even having a moment right now which are fun with dresses.


Update Your Short Shorts

I like to call these coochie cutters. Not flattering unless you’re a stick. And honestly, even then, I just think this is a dated style. The low rise, low inseam, not good. Instead, we’re doing a higher rise (makes our legs look longer) and a longer inseam which is more comfortable, more age-appropriate, and just feels better. You can also feel more comfortable in a heel if you have a longer inseam. I have a BIG post on my favorite shorts that you can check out here and here.


Update Your Workout Wear

This is what sparked a lot of this, I realized I was rocking a very outdated 2015 outfit while on a Hot Girl Walk. Sure the look on the left isn’t horrible at all. And the look on the right isn’t groundbreaking. But let’s be honest, the capri, the super long tank, it definitely feels a bit dated. It’s fine for getting a work out in, I’m not really too picky there. But when it comes to a fitness class or wanting to go on a Hot Girl Walk, we want an updated chic look.

So let’s get rid of the mismatched items, the capris (these just aren’t very flattering, go the full length or biker), and let’s infuse some style and personality into these outfits. We’re also getting rid of any super short shorts because we enjoy a longer inseam now in our 30s and 40s. But hey if you got the bod for it, rock it. But for 2022, I’m loving matchy matchy sets, workout skirts and dresses, longline bras, cropped tops and accessorizing the look to go from Hot Girl Walk to lunch with friends.


Update Your Work Outfits

The neon earrings, the floral print shoes, it’s a lot. And that’s what we’re leaving behind. Along with a slew of other things like too tight of pants with a giant button down and ballet flat. Instead, let’s try for wide leg trousers, or even tapered ones like these. And if you want to do a skinny work pant, let’s pair it with tailored pieces and good layering. You can see 3 ways to style the M.M. LaFleur Curie pant here which is a great skinny work bottom to wear if you want to hold on to your skinny silhouette. Pair it with longer blazers. Or try an oversized sweater with a chunky lug sole loafer for an udpated look.


Update Your Going Out Tops™

Okay, hear me out. We don’t need an entire section of our wardrobe for going out tops. There, I said it. It’s okay to wear your basics out. Wear a sleek white tee with gold layered jewelry and a cool blazer. Wear a simple black bodysuit with your favorite relaxed denim and some high heels. Or just go for a really beautiful silk button down. The top doesn’t have to scream Going Out Top™. Let the accessories do the talking as I’m sure you have great jewelry, shoes and maybe a great bag, that can transform jeans, trousers or skirts, into a fabulous going out ensemble that feels elevated.

Also, we can skip the Going Out Tops™ and opt for wearing dresses. I’m a big fan of a slip dress like this one or a slip style maxi like this.


Update Your Summer Dresses

I cringe at what my eyes have to see here. The bold printed asymmetrical summer dresses. Or dare I say, the chevron polyester dresses. If you haven’t updated your summer sundresses in a decade, it’s time. Opt for summer slip dresses, linen sets like this one from Reformation, classic white button front dresses – these are all good choices. And leave the fitted crop denim jacket and swap it for an oversized one. Especially if your dress is mini and fitted. It creates the perfect balance and proportions.


Update Your Flannel Plaid Shirts

Let’s chat proportions. On the left we have all fitted things. Fitted tee, skinny jeans, sleek sneakers. And just a stupid plaid shirt wrapped around our waist. It’s serving us no purpose, it’s a lame accessory. Instead, we’re swapping it out for something more oversized that we’re going to aactually wear, and wear it as a light layer. We’re wearing it over a slightly oversized tee paired with skinny jeans if you wish (i’m opting for faux leather leggings, and then a chunky boot to balance it out.


Update Your Bag

One of the easiest ways to instantly make your outfit more interesting is by taking the time to select an on trend bag. Let’s leave the nylon Longchamp totes behind, and the logo-covered LV Neverfull bag that every girl had in the 2010s. There are so many wonderful tote bags for the office, for travel, for the beach, that are stylish and functional. For fall and winter, try a leather zip top tote. And for spring and summer, try a woven tote instead. This is the easiest way to make an outfit feel updated and more interesting at the same time. And if you need a travel bag, you can use those for it too! That way you have a beautiful bag to wear when you land.


Update Your Jewelry

Promise me you got rid of the bauble necklace. Promise?? These were horrific. I can’t believe how many giant statement plastic, piece of crap, necklaces I owned. BYE! Instead, it’s about layering gold or silver jewelry, whichever you prefer, or mix them! Giant statement pieces to me aren’t really having much of a moment anymore. Stick to simpler items, effortless layering, and maybe a good gold hoop. I do think there’s some fun to be had in layering colorful bracelets or rocking a fun earring, but do this sparingly in my opinion. Jewelry also feels very personal sometimes, so do with this info as you see fit. But let’s maybe all agree to retire anything we’d consider a “bauble”.


Update Your Accessories

Let’s talk about the accessories. The belts, scarves and such. Gone are the days of throwing on a thin infinity scarf to make your outfit feel complete. Instead, we’re using a little silky bandana or adding a great belt. There’s no need for a scarf unless you are physically cold and need to be warmed up. The beloved blanket scarf can also be retired. We are investing in real scarves these days. Real belts that function and add interest. Those are the accessories we want these days. PS my favorite ways to style a belt!




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