My fall denim refresh spans six jeans across four brands: a $30 bootcut deal from Ann Taylor, a dark ankle straight leg from PAIGE, a brown wide-leg from Wit & Wisdom, and three from Talbots — a classic wide-leg, a cuffed relaxed straight leg, and a trouser pull-on. Each one earns its spot for a different reason, not because one look is the whole story.
What You’ll Find In This Post:
Why I’m Reaching for Denim Right Now
The straight-leg jean in these photos, cuffed and worn with a tweed jacket, is one look among several I’ve had on lately as the mornings cool off. This is the perfect time to talk about denim, because there are so many cuts and styles out there, and I’m looking to balance my classic denim staples with some more adventurous options this fall. Back in January I walked through the seven denim trends I’m actually wearing after 50 — think of today as the fall shopping list that goes with it.
So today’s edit is six jeans across four brands — a boot flare, a dark ankle straight leg, a brown wide-leg, a classic wide-leg, a cuffed relaxed straight, and a trouser pull-on. Different silhouettes, different price points, different reasons each one is worth knowing about. A couple of these lean into this fall’s warm-neutral palette, which is where the brown pair comes in.
A quick note on fit before we start: I’m 5’8″ and a size 8, and I’ll tell you under each pair whether I’ve worn it, ordered it, or am still eyeing it. You deserve to know the difference.
The Edit
6 Jeans Worth Shopping This Fall
1. The Under-$50 Steal
The Boot Jean — Ann Taylor
$30.00, marked down from $129.00
Why it works: A high-rise bootcut in a bright mid-indigo wash — the silhouette that actually looks right with a boot or a low heel, since a flare needs somewhere for the leg to go. The price on this one is a genuine steal, though it’s final sale, so double-check your size before buying.
How I’d style it: Ankle boots and a fitted sweater so the flare has room to move without getting lost.
2. The Polished Splurge
The Dark Ankle Straight Leg — PAIGE
$143.40, marked down 40% from $239.00
Why it works: A dark indigo, ankle-length straight leg with just enough polish to work for dinner out. This is the splurge of the group, but the wash and the cut are the reason a straight leg can look dressy instead of just casual.
How I’d style it: Tucked-in blouse and a slingback heel — the ankle length is made for showing a little shoe.
3. The Colorful Pick
The Brown Wide Leg — Wit & Wisdom
$94.00 (runs slightly large, per reviewers)
Why it works: Brown denim is the real trend piece in this edit — a washed dark walnut wide-leg that works the season’s warm-neutral palette without giving up jeans entirely. It’s the one pair here I’d call a genuine style risk, and the one I’m most curious to actually try.
How I’d style it: A cream sweater and gold jewelry so the brown reads intentional rather than muddy — and consider sizing down given the fit note.
4. The Wide-Leg Pick
The Classic Wide Leg — Talbots
$129.00 (currently 30% off with promo)
Why it works: A medium-wash wide leg with a retro patch-pocket detail — this is the denim-blue version of the wide-leg silhouette, for anyone who wants the trend without the brown.
How I’d style it: Tucked sweater on top, suede loafers or a low boot underneath, so the leg has a clean line to fall through.
5. The Everyday Pick
The Cuffed Relaxed Straight Leg — Talbots
$109.00 (currently 30% off with promo)
Why it works: The closest match to what I’m wearing in today’s photos — a relaxed straight leg with a built-in cuffed hem in a medium wash. The wash and cut are flattering and versatile, and the cuff adds some unexpected sass.
How I’d style it: Exactly as before — tweed jacket, simple knit, ballet flat or kitten heel.
6. The Travel-Ready Pick
The Trouser Pull-On — Talbots
$129.00, (currently 30% off with promo)
Why it works: No zipper, a clean trouser front, and a dark wash that reads more polished than a typical pull-on. This is the pair for travel days or anywhere comfort needs to win without looking like it did.
How I’d style it: A button-down tucked in and loafers — the trouser shape does most of the dressing-up on its own.
How to Shop This Many Silhouettes Without Overbuying
- Pick your silhouette before your wash — flare, straight, or wide leg changes what shoes and tops actually work, more than color does.
- Let the dark wash do the dressing up — a darker rinse reads more polished than a lighter one, no matter the silhouette.
- Try brown before you commit — it photographs differently than it looks on the hanger, and fit can run large, so read the reviews.
- Keep one pull-on or trouser style in rotation — for travel days or anywhere comfort has to win, it can still look intentional.
- If your top won’t tuck, don’t force it — a waistband-length knit or a cropped jacket gives the same clean line without the tuck. (Barbara, this one’s for you.)
FAQs
Wide-leg and straight-leg silhouettes in both denim-blue and warmer washes like brown are the standout options this fall — wide leg is having a real moment, but a dark straight or ankle pair remains the more versatile everyday choice.
It’s showing up across several brands this season as part of a broader warm-neutral palette, so it’s worth trying if the rest of your closet leans cream, camel, or olive — but it’s not necessary to replace your existing denim-blue jeans.
The Talbots trouser pull-on — it’s well reviewed, dresses up more easily than a typical pull-on, and works for both travel and everyday wear without a second thought.
Closing Thoughts
Fall is a great excuse to try a silhouette you might not normally reach for — a flare instead of your usual straight-leg, a wide leg instead of a skinny, even a color like brown or sage instead of blue. (And yes, white jeans in fall count too — I broke my mother’s rule on that one this week.) None of these requires replacing what’s already working, just adding a new shape into the mix. I’m curious: which of these six cuts are new to you, and which ones are you going to try out? Let me know in the comments!
Before You Go
What does your denim wardrobe need this fall? Are you sticking with a favorite straight-leg jean, trying a wide-leg or bootcut silhouette, or adding a darker wash for a more polished look? Tell me in the comments — I always love hearing what’s actually working in your closets.
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Shop the Post
Ready for a denim refresh? Here are all six pairs featured in today’s post:
- Ann Taylor Boot Jean — Shop here
- PAIGE Cindy High-Waist Ankle Straight-Leg Jeans — Shop here
- Wit & Wisdom Sam High-Waist Wide-Leg Jeans — Shop here
- Talbots Relaxed Wide-Leg Jeans — Wainscott Wash — Shop here
- Talbots Everyday Relaxed Jeans — Beale Wash — Shop here
- Talbots Trouser Pull-On Travel Jeans — Pike Wash — Shop here
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