Key Takeaways
- Deepest cut of the week: The Premium 6 Inch Lace Up Boot in dark blue canvas is sitting at 82% off, the kind of markdown Timberland rarely lets happen on the women’s icon silhouette.
- Trail-ready waterproof: The White Ledge Waterproof Hiking Boot and the Linden Woods 6-Inch Waterproof both have seam-sealed leather uppers built for mud and creek crossings.
- Work shoe value: Two Timberland PRO athletic work shoes, the Radius and the Setra, both have composite safety toes and sit in the mid 50s after the markdown.
- Range of the post: Discounts run roughly 41% to 82% off, with the steepest cuts on the 6-inch lace up silhouettes.
- Prices verified May 29, 2026.
- What are the best Timberland women’s lace up boots right now?
- Which Timberland waterproof boots handle WV trails best?
- Are Timberland chukkas and sneakers a good lace up alternative?
- What about Timberland PRO work shoes for women?
- One Chelsea pick if you’d rather skip the laces
- Frequently asked questions
Late May in West Virginia is the strange in between week where the morning trail is still wet from runoff and by Saturday afternoon you’re out in a t-shirt looking at the rhododendron coming in along the creek. Most folks I know are pulling cooler bags out of the basement and trying to figure out what shoes are going to survive Memorial Day weekend at the cabin. My old pair of Timberlands lived through three deer seasons before the eyelets gave out, so I have opinions when a stack of them go on sale at once.
This week’s WV Finds column lands on a deep batch of Timberland and Timberland PRO markdowns, and the women’s lace up boots are doing most of the heavy lifting. The Premium 6 Inch in dark blue canvas is the headline, sitting at the lowest price I’ve tracked on it in months, and it’s the same silhouette people have been searching by exact color name. There are also two waterproof field boots in here, the White Ledge and the Linden Woods, both of which I’d genuinely consider for a wet Cranberry Wilderness day.
What follows is heavy on the 6-inch lace ups, with a couple of chukkas and a pair of Timberland PRO work shoes for anyone clocking in on their feet. One Chelsea pull-on snuck in at the end for readers who hate dealing with laces.
What are the best Timberland women’s lace up boots right now?
The strongest women’s lace up deals are clustered on the classic 6-inch silhouette and the Stone Street mid. Each of these has the wheat-style lacing system Timberland is known for, and all three are sold and shipped by the retailer rather than a third party.
Timberland Premium 6 Inch Lace Up Dark Blue Canvas
Timberland Women's Premium 6 Inch Lace Up Boot, Dark Blue Canvas, 5.5 Medium
This is the deal that pulled the whole post together. The Premium 6 Inch Lace Up in dark blue canvas matches one of the most specific keyword searches I see on Timberland women’s boots, and the size 5.5 medium is the one with the heaviest markdown right now. Canvas upper means it breathes better than nubuck in summer, but you do lose some of the rain resistance of the leather versions.
- Canvas upper, breathable for summer
- Classic 6-inch wheat-style lacing
- Size 5.5 medium, women's
Timberland Stone Street Mid Lace Up Grey
The Stone Street Mid Lace Up in grey is a slimmer, more street-leaning silhouette than the iconic Premium boot. It sits at the ankle rather than the calf and has a lower profile lug, which makes it easier to wear with cropped jeans or work pants. Size 9.5 medium is the one in stock at this price, and the deal has a posted end date so it’s not going to sit forever.
- Lower-profile ankle silhouette
- Grey colorway
- Size 9.5 medium, women's
Timberland Premium 6 Inch Waterproof Red Nubuck
Timberland Women's Premium 6 Inch Lace Up Waterproof Boot, Medium Red Nubuck, 6 Medium
If you want the same Premium 6 Inch silhouette but in nubuck leather and waterproof, the medium red nubuck version in size 6 is the pick. Red nubuck is a love or hate color and it darkens with wear, but the waterproof construction is the real reason to grab this one over the canvas. Good for a damp Saturday morning at Cooper’s Rock when the leaves are still wet.
- Waterproof nubuck leather
- Medium red colorway
- Size 6 medium, women's
Which Timberland waterproof boots handle WV trails best?
For actual trail use, the White Ledge and Linden Woods are the two I’d point readers toward. Both have seam-sealed waterproof leather and lugged outsoles, and both carry low bestseller ranks in the women’s hiking boot category.
Timberland Linden Woods 6-Inch Waterproof
Timberland Women's Linden Woods 6-Inch Waterproof Boot, Medium Brown Full Grain, 10 Medium
The Linden Woods 6-Inch is a workhorse. Medium brown full grain leather, full lacing, and a tall enough shaft to keep mud out when you’re crossing a wet section of the Greenbrier River Trail. The size 10 medium is the one moving at this price, and the bestseller rank under 100 tells you this model has staying power. Not a fast hiker, more of a sturdy walk-and-work boot.
- Full grain leather, seam-sealed
- Tall shaft for mud and creek crossings
- Size 10 medium, women's
Timberland White Ledge Waterproof Hiking Boot
Timberland Women's White Ledge Waterproof Hiking Boot, Beige, 10 Medium
The White Ledge in beige is the lighter, more technical hiker of the two. It has a more contoured fit and a stiffer shank for steeper climbs, which is the move if you’re doing rocky stretches up around Seneca or Dolly Sods. Size 10 medium is what’s listed. This one was added two days ago, so the price drop is still fresh.
- Stiffer shank for rocky trails
- Beige leather, lugged outsole
- Size 10 medium, women's
Are Timberland chukkas and sneakers a good lace up alternative?
Yes, especially if you want lace up styling without committing to a 6-inch boot. Both of these have softer linings and a much lower-profile lacing setup.
Timberland Rowan Way Warm Lined Chukka
Timberland Women's Rowan Way MID WARM LINED CHUKKA BOOT, BLACK, 9 Medium
The Rowan Way Mid Warm Lined Chukka in black is built for shoulder seasons, with insulation that’s warm without being a winter boot. The chukka height means you can tuck jeans over it cleanly. Size 9 medium is the listed pair, and it’s one of those boots that reads dressier than you’d expect from Timberland.
- Warm-lined chukka height
- Black, shoulder-season boot
- Size 9 medium, women's
Timberland Skyla Bay 2.0 Low Sneaker
Timberland Women's Skyla Bay 2.0 Low Warm Lined Sneaker, Rust Suede, 9 Medium
The Skyla Bay 2.0 Low is a warm-lined sneaker, which is an odd combination on paper and works in practice. Rust suede upper in size 9 medium, with a wider, flatter lace pattern than the boots above. Good for running errands on a cold morning when you want something between a boot and a regular shoe. Bestseller rank is the highest on the list at 2,610, so it’s a little more niche.
- Warm-lined sneaker, rust suede
- Lower-profile lacing
- Size 9 medium, women's
What about Timberland PRO work shoes for women?
Two Timberland PRO athletic work shoes made the cut this week, both with composite safety toes that are lighter than steel and won’t conduct cold. These are aimed at warehouse, lab, and trade work where you need protection without a full work boot.
Timberland PRO Radius Composite Toe Work Shoe
Timberland PRO Women's Radius Composite Safety Toe Athletic Industrial Work Shoe, Black, 10W
The PRO Radius in black, size 10W, is the sleeker of the two. Composite safety toe, athletic last, and a lace up sneaker silhouette that doesn’t read as a work shoe at first glance. This one was added two days ago and the bestseller rank is solid for the category.
- Composite safety toe
- Athletic last, sneaker silhouette
- Size 10W, women's
Timberland PRO Setra Composite Toe Work Shoe
Timberland PRO Women's Setra Composite Safety Toe Industrial Athletic Work Shoe, Green/White-2024 NEW, 8 M US
The PRO Setra in green and white, size 8 M, is the newer 2024 model and has the lowest bestseller rank of any women’s work shoe in this list at #92. Composite toe again, same general athletic build, and the green and white colorway pops a bit more if you don’t want straight black. Worth a look if you’re on your feet ten hours a day.
- 2024 model, composite safety toe
- Green and white colorway
- Size 8 M, women's
One Chelsea pick if you’d rather skip the laces
Not everybody wants to bother with lacing up a 6-inch boot every morning. Here’s the one Chelsea pull-on I’d point you toward in this batch.
Timberland Brimfield Mid Chelsea Boot
Timberland Women's Brimfield Mid Chelsea Boot, Black Full Grain, 9 Medium
The Brimfield Mid Chelsea in black full grain leather is the cleanest pull-on Timberland makes right now. Elastic side panels, no laces, and a low-key lug outsole. Size 9 medium is the one priced down. This one is good for someone who wants the Timberland leather quality without the construction-boot look.
- Pull-on Chelsea, no laces
- Black full grain leather
- Size 9 medium, women's
Frequently asked questions
Are Timberland women’s lace up boots true to size?
Most women’s Timberland lace up boots run a touch large, and the brand’s own guidance is to size down half a size if you’re between sizes. The Premium 6 Inch and Stone Street fit similarly. The waterproof leather versions can feel tight at first and break in over two or three wears.
What’s the difference between the Premium 6 Inch and the White Ledge?
The Premium 6 Inch is the iconic wheat-style fashion boot with a flat lug sole, designed more for streetwear and light outdoor use. The White Ledge is a true hiking boot with a contoured fit, stiffer shank, and a more aggressive outsole pattern for trail traction.
Are Timberland PRO work shoes the same fit as regular Timberlands?
Not quite. Timberland PRO uses a wider, more athletic last with extra room in the toe box for the safety toe cap. Most people size the same as their regular running shoe rather than their Timberland boot size.
Will canvas Timberlands hold up in West Virginia weather?
Canvas versions like the dark blue 6-Inch will get wet through if you stand in a creek, but they dry faster than leather and breathe better in summer. For wet trails and shoulder seasons, the waterproof nubuck or leather models are the better choice.
How often do Timberland women’s boots go on sale this deep?
Markdowns above 70% on current women’s silhouettes are uncommon outside of major sale events. The Premium 6 Inch dark blue canvas at 82% off is the deepest we’ve tracked on that style in recent months. Prices verified May 29, 2026.
Across the ten picks the markdowns run from about 41% off on the Linden Woods up to 82% off on the dark blue Premium 6 Inch, with most of the lace up boots landing in the 55% to 75% range. That’s a wider spread than I usually see in a single brand post, and the depth on the women’s icon silhouette is what makes this week stand out. The Timberland PRO work shoes sit in a tighter band in the low to mid 50s, which is in line with how often those go on sale.
The honest take: this is a strong week for women’s Timberland lace ups, weaker for everything else. The standout is the Premium 6 Inch in dark blue canvas, both because the price is unusual and because it matches one of the most searched color and silhouette combinations on the brand. The Linden Woods is the one I’d grab for myself for real outdoor use. The Skyla Bay sneaker is fine, but it’s a softer recommendation, more of a niche pick. If you missed last week’s hiking boot roundup, those deals are still worth a browse for cross shopping against the White Ledge.
Looking at next week, I’d expect Timberland to keep the cuts on the older size runs and possibly add to the chukka and Chelsea models as Memorial Day promo windows expand. The 6-inch Premium markdown is the one I’d move on first if it’s your size, because that style tends to bounce back to full price faster than the work shoes. The PRO work shoes will probably hold this price band into June.
