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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Sorry, Barrel Jeans—I Am Forever Loyal to This Classic, Effortless Denim StyleFive chic winter outfit ideas right this way.
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This Pop Star's Shoe Collection Is Full of Unexpectedly Chic Gems—25 I Have My Eye OnMost styles are under $100.
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3 Cheap(ish) Elevated Finds That Will Make Your Closet Look More ExpensiveUnder $150 and super chic.
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32 No-Fuss, Elevated Items That Ooze Capricorn VibesFrom classic blazers to designer pieces.
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I'm a Fashion Editor—I Reach For This Effortless Wardrobe Essential When I Don't Know What to WearHere are nine easy ways to style the piece.
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My Style Is Thoughtful and Tasteful—30 Must-Have Luxe Pieces I'm Shopping for This WinterA+ finds.
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10 Wardrobe-Improving Things to Buy in JanuaryYour monthly shopping list.
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You Had Me at Cashmere Sale—30 of the Chicest Finds to Shop Before They Sell OutYou'll wear these forever.
