While every season poses its own challenges in terms of styling outfits and shopping, I find winter to be one of the most difficult. Of course, being an L.A. native now living on the East Coast doesn’t help, but I will say I’m proud of how far I’ve come in the last seven or so years in terms of learning how to dress for actually cold weather while maintaining some semblance of my personal style. It wasn’t easy, but I’ve finally learned what works and doesn’t work, as well as what pieces are essential (such as scarves) and which simply should be skipped (think: ankle-bearing pants).
Speaking of those essential items—today, I’ve found the most expensive-looking versions of this year’s key winter basics and trends, all under $49. From jeans and jackets to boots, knits, and everything in between, below you’ll find nearly 50 outfit upgraders that won’t break the bank but will have you looking like a million bucks. Ready to get started? Simply keep scrolling.
Your new night-out top.
You can't not look polished in trousers.
Everyone is wearing this shoe style right now.
If you live on the West Coast, this could quite possibly be your only winter coat.
Love me a cable-knit sweater.
A small belt can make such a big impact.
Every time I look at Zara's denim selection, I start hating all my other pairs.
A must.
I love how polo sweaters look layered over white tees.
I live in this T-shirt.
It's giving rich mom.
Sometimes, it's just beanie weather.
Because who has time to take their gloves off to text?
Try to convince me these don't look expensive.
I want to live in this.
It's not under $49, but I still urge you to consider the matching blazer coat.
Hailey Bieber vibes.
Here's that pop of red you've been hearing so much about.
It's all about oversize right now.
That little bit of wool makes all the difference.
Zara boots never disappoint.
You can layer so much underneath this.
This top can go with anything from jeans to a skirt.
New season, new sunglasses.
Obsessed with how this is styled.
Chic.
Belts make every outfit better.
Okay, it's $49.95, but I needed you to see it!
Don't underestimate the importance of great basics.
Simple yet so chic.
It's obvious why our readers love this dress.
These tights are magical.
Three is better than one.
Hands down, vests are my new favorite top.
So obsessed with slingbacks right now.
Intrigued to say the least.
I'm all about the mod minidress lately.
Bangles are back!
Cozy but chic.
They knew what they were doing making this in four colors.
Flat slingbacks might be my next shoe purchase.
Getting dressed in the morning would be so much easier if I had this.
Everyone needs a pair.
When J.Crew says perfect, I take it literally.
For all your holiday party needs.
I'm obsessed with how this is styled.
Who passes up a $20 leather belt?
This shade of gray is so luxe.
My motto with scarves this season is the bigger, the better.
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These $50 Old Navy Zipped Boots Are Just as Chic as the $1500 Pair I Have Been Coveting Since Last WinterThey're on sale for $30 right now.
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25 Elevated Basics Worthy of a Fashion Person's Closet From Gap, Banana Republic, and Old NavyWho's in need of closet refresh?
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My Stylish Aunt Asked What She Should Buy From Old Navy—Here's Every Under-$50 Item I SuggestedCurrently on sale.
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My Friends Love Reformation—I Sent Them 31 Gorgeous Picks I'm Eyeing Right NowOne of each, please.
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My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic, Rich-LookingReplica Store FindsEverything is under $150.
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H&M Just Dropped a $40 Version of The Row's Winter Flats I Keep Seeing on Chic New YorkersA sellout is imminent.
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The 30 Items Set to Define Winter 2025 FashionWhat to buy before the temperatures drop.
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Looking Chic This November Means Owning These 10 ItemsBring on the compliments.
