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High-waisted, wide-leg pants are having quite the moment. One that I don’t want to ever end — for my limbs to be draped in excess fabric makes my heart flutter and makes dressing up (whether for work or for play) so much easier. Never overdesigned and often actually comfortable (hard pants can also be soft, go figure), they’ll make you look put-together without feeling too fussy. Pair them with your sweaters and oversize coats, and you’re instantly cosplaying a The Row model without the price tag — unless you can actually afford the Olsen-owned brand, which I commend.
Regardless of your style inspiration, I’ve rounded up 16 of my favorite wide-leg pants for fall and winter weather. From high-waisted, wide-leg trousers that feature a relaxed drape, a flattering inseam, and a comfortable waistband to tailored selects that are effortless and easy to wear, I made sure to include the best. The vast majority are ones I use year-round from brands that are hanging in my closet, while others are pairs that my group chats swear by.
The Best Casual Wide-Leg Pants
I’ve been drinking the A&F juice and I’m not ashamed to say it. Its tailored wide-leg pants fit true to size, are available in multiple colorways, and are under $100. Mine have been in heavy rotation this year because they work well with kitten heels, ballet flats, and every sneaker in my closet.
The Extra High-Waisted Pants
The Power Pants
The Under -$50 Wide-Leg Pants
If your closet looks anything like mine, most of your white- and beige-colored trousers are made from lightweight linen, which should be reserved for warm weather. For the fall and winter months, these elevated cotton trousers from COS are a nice alternative.
The Best Dressed-Up Pajamas
These silky monogrammed pants from Toteme are the best of both worlds: You get the comfort of pajamas with the polished look of wide-leg trousers.
The Under-$100 Wide-Leg Pants
Oak + Fort pants are in my top-ten favorites. The pairs I own fit to a T and always get me so many compliments. Luckily, the brand’s NYC brick and mortar is back on Spring Street, so you can try them on before purchasing. Mine run true to size, but you never know.
The Real Leather Wide-Leg Pants
The Luxe Choice
We can’t mention The Row in the intro and not include it in the roundup. Go ahead, click the link, and fantasize how these almost $1,500 pants will fix all your problems.
The Best Wide-Leg Pants for Work
I can always count on Anine Bing for stylish workwear that transitions well to happy hour or date night. These trousers are the perfect example. The tailored silhouette and concealer zip-front closure look so professional, but the side-slits and houndstooth print give them a bit of edge.
The Structured Wide-Leg Pants
If you’re bored of black trousers but love the versatility of a neutral color, try this gray pair by Elleme instead. The wide-leg fit combined with the wide waistband feels unexpected and fashion forward.
The Wide-Leg Pants in Bright Blue
The Festive Pair
Be prepared for upcoming holiday parties with these timeless velvet pants that feature a subtle sheen (and look so much cooler than the average cocktail dress).
The Relaxed Wide-Leg Pants
It’s no surprise that the brand known for wardrobe essentials and smart suiting makes a great wide-leg trouser. If you want casual pants that will last you for years, look no further than these buttery-soft leather ones that have an elastic waistband and an oversize fit for maximum comfort.
A Statement Pair of Wide-Leg Pants
High-waisted, wide-leg trousers don’t have to be overtly classic or traditional. This Max Mara pair, for example, has an asymmetrical waistline that creates a statement-making wrap effect. The 100 percent wool fabric combined with the extra-baggy design adds even more drama.
The Striped Wide-Leg Pants
A solid under-$150 option that will look great with a simple white tank or a color-blocked blazer. Choose your fighter!
More Holiday Dressing
- Holiday Dressing, According to Young Emperors
- How to Style a Party Skirt
- A Simple Guide to Stylish Holiday Dressing