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. So today I want to chat about ways to update your basic Millenial outfit.
Sometimes outfits need a little updating. And sometimes your closet needs a little refresh. 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 Millennial trends I think many of us willfully gave up. For me, it was the ever so popular Millennial chevron patterns, the long necklaces that were neon and chunky, the bright 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 few years now that you are in need of a wardrobe update and ways to update your basic Millenial outfits. You feel stuck in your Millennial style trends but don’t know how to update your look. You still love our skinny jeans and just don’t know how to make things look updated. 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 is all about understanding the new fits, styles 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, check out SketchyMandy and Being Julia. I’ve found their content to be super helpful!
19 Ways To Update Your Basic Millennial Outfit
Before we dive in, I want to remind you of something. 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. I think it’s 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 I’ll show you the ways to update your basic Millenial outfit so you can feel GOOD.
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.
1. Update Your Basic Skinny Jeans
It’s true, you don’t have to toss your skinny jeans if you’re updating your Millennial wardrobe. 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 still around, it’s really only happening in the mom jean style. And we aren’t seeing a TON of distressing either, it’s definitely cooled off a bit.
If you want to swap your skinny jeans and try something new, I would suggest a straight leg jean that’s tailored. It’s not sloppy nor is it baggy. And a straight leg jean will 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 and is a great place for Millennials to shop to feel up to date.
2. Update Your Utility Jacket
Oh, the security blanket this utility jacket was for me. The photo on the left is your quintessential 2012 Millennial outfit. Low rise skinny jeans (cuffed at the bottom) with white Adidas, a striped tee and a basic utility jacket. It was a classic Millennial trend and I was a big fan.
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 maybe even swapping for an oversized barn jacket as seen here.
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. And you can even try a cropped boxy fit. Just avoid super fitted ones and we aren’t seeing this as much.
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3. 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 Millennial fashion booties out in about 7 years, it’s probably time. Any cutouts, or super low-shaft ankle booties showing off those ankles, are probably a no as these were Millennial fashion trends we coveted from the early 2000s and even 2010s.
For 2026 style trends, 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. And a general rule of thumb is that we are no longer showing off our ankles.
I personally 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.
4. 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 roomy tee underneath.
Otherwise, if it’s a really snug blazer, I’d probably swap it out. I love a longer-lined blazer too. But any relaxed fit, slightly oversized blazer, is a great update to the Millennial fitted blazer trend we loved. Note the denim swap too above. Skinny jean to straight leg.
5. Change Out Your Cardigans
We lived, and I mean LIVED, in our mid-thigh lightweight cardigans. They were a go-to to wear over our beloved skinny jeans and wear to the office. While I have gotten rid of all of mine, there are styles of cardigans that work for 2025 and 2026.
And I feel like there are two major Millennial style updates. Either you go super super long in a duster which also still works with skinny jeans, leggings and even a straight-leg jeans. Here are a few good examples of how to wear a long cardigan. Or you go cropped.
A cropped cardigan is basically just a normal sweater, but a cardigan style with buttons. You can wear it open with a fitted sweater tank underneath it. Or wear it as a whole sweater buttoned up.
6. Update Your Fitted Jean Jacket For A Relaxed Fit
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 shrunken denim jacket for a few updated oversized denim jacket styles. I also think swapping for a shacket is a great idea too like I did here.
You can also try a cropped slightly oversized denim jacket. Not to throw you through a loop here, but this does fit well with looser fitting bottoms like the 90’s baggy jean trend and trousers. Just steer clear of anything super fitted! Cropped does not necessarily equal fitted!
7. Say Goodbye To The Old Riding Boots
I was never into the riding boot trend (the look on the left was the one and only time I ever did a sweater dress and riding boot outfit). 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 for 2025 and 2026. It’s also about the styling. We’re not wearing them 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.
8. Update Your Short Shorts For Longer Inseams
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 (which makes our legs look longer) and a longer inseam.
The longer inseam is honestly 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. These are the best summer shorts I love and here.
9. 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 shorts), 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 2026, 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.
10. Refresh 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. This style of pant 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 updated look.
11. Update What You Pair With Your Ballet Flats
While I don’t think you need to swap the flat out (unless you’re still rocking your Tory Burch gold emblem ones, those can go, friend) let’s update how we’re styling them. Instead of pairing them with your skinny jeans, a tight blazer, and a fitted shirt, let’s loosen it all up. 90’s relaxed jeans, a slightly oversized blazer or a chunky sweater, and you’re good.
Ballet flats are super feminine and minimal, so pair them with something that offsets that. And if you’re feeling like a ballet flat is no longer your personal style vibe anymore, try a chunkier loafer for a flat update!
Let’s also note the blazer swap here. Instead of super fitted, for everyday outfits, we’re seeing more oversized proportions. While I think a classic more tailored fit is great for the office or business casual, for everyday with jeans and a tee, go more oversized. And especially a bit longer in the length.
12. 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 that’s the perfect maxi dress for date night.
13. Say Goodbye To High-Low Hems And Update Those 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 when updating your Millennial style.
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. For more Millennial style swaps, check out ways to update your basic Millennial outfits for summer here.
14. Update Your Flannel Plaid Shirts And How You Style Them
Let’s chat about proportions. On the left, we have all the 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 actually wear, and wear 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. You can also check out this post on how to style a flannel that feels updated.
If you do want to style a flannel around your waist, try pairing it with more updated pieces. Wider leg jeans, a cropped jacket and so on. When your whole outfit includes dated pieces, this accessory can feel off. But it somehow feels fresh and cool when styled with more oversized items. Or you can try this fun trend of tying a thin sweater around your natural waist slightly off centered. Tie it at your waist to create shape and add color to your look. Here’s a good example of an updated way to tie a piece around your waist.
15. Time For A Tote Bag Update
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.
Bags can quickly date or update your Millennial outfit. If you want to know how to not dress like a Millennial and feel dated, try updating your everyday bag.
16. Reach For Minimal Layered Jewelry
Promise me you got rid of the giant bib bauble necklace. Promise?? These were horrific. I can’t believe how many giant statement plastic, piece of crap, necklaces I owned as a Millennial in the early 2000s. 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. Instead, 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 always has trends that change over time and each year it can be fun to add something new to the mix. But if you want to play it safe and find longevity in your pieces, I think minimal is best.
Jewelry can also feel very personal at times, so use this information as you see fit. But let’s maybe retire anything we wore in the 2010s that are definitely no longer available today.
17. Let’s Update Your Everyday Accessories
Let’s talk about accessories as one of the best ways to update your basic Millennial outfit. 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!
If you even keep the rest of your basic Millennial outfit the same, but update all of the accessories, you’ll instantly transform your Millennial outfit with ease.
18. Update Your Button Downs
Gone are the days of a super fitted and tailored button down. We are seeing more loose and oversized button downs for women. If you are going into the office, this can be an easy update that will make your outfits feel a bit elevated almost instantly. Whether pairing with trousers or skirts, this is an easy swap.
Plus in your more casual style and outfits, swap out fitted button downs for super oversized ones. Remember to balance with something more fitted on the bottom (maybe not skinny jeans if you can help it), but a slim straight leg is perfect.
19. Update Your Socks
One of the telltale signs that you’re a Millennial who hasn’t been paying attention is to look at your socks. I know it can be challenging to know WHAT to do, but that’s what I’m here for. You can explore my entire guide on which socks to wear with what shoes here. And that’s why I chose the above before and after. I would add a white crew sock to these black leggings if I was going for a walk. And now, I’d wear a crew sock or lettuce hem sock with a sneaker and a workout outfit as you see on the right.
Whether it’s your workout outfit and adding a cute crew or lettuce hem sock, or pairing a fun colored sock with your loafers or ballet flats, socks are to be SEEN now. For the most part. I am still fine with wearing a no show with some of my socks. But when I do want to put on a fashionable outfit, and not just be running a quick errand, I find my sock choice will definitely change.
What Is Millennial Fashion?
If you’re unsure of what Millennial fashion actually is, let me give you a little rundown. First let’s chat. Who are Millennials? They are Generation Y who were born between 1981 to 1996. And Millennial fashion trends that we are notorious for include chevron prints, hi-low hemlines, low rise jeans, skinny jeans and lots of statement ankle booties to name a few.
As Gen Z, the generation born between 1997 and 2001, have come onto the scene and make their fashion mark, the Millennial fashion trends some of us have been holding onto, have been getting dragged. Which is funny since many of the Gen Z fashion trends happening now are very reminiscent of Y2K from low-rise flared jeans, tube tops, camisoles and the beloved claw clips.
But I think we can all agree that the Millennial fashion trends that we associate with our late teens, early twenties fashion is what’s in desperate need of a bit of a refresh. No, you don’t need to dress like a Gen Z TikTok star, but I think it can feel good to make some necessary swaps. to update our basic Millennial style and feel more confident in our clothes. And I hope these simple swaps help you do just that.
