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Happy Feet: Good Gifts (including the Comfiest Boots) for Hardworking Soles

Best, most comfortable boots plus at-home pampering gifts for your poor, tired soles -- or someone else's.
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Boot Love

I've been boot-obsessed this season. Yes, it's possible I've acquired more pairs than perhaps I should have, but I've also lucked out with some of the most comfortable pairs I've ever met in my life. (It's a numbers game. That's my theory and yep, I'm sticking to it.)

If I've made you try on my waterproof Timberland Earthkeepers Rudston boots ($240), you're already familiar with my enthusiasm for them. [UPDATE NOV 2014: the Rudstons have been discontinued; these Stratham Heights boots are a handsome alternative.] Second from the left in the image above, they're genius, wear-all-day heels, even on days that involve running around. The comfort is unbelieveable -- like wearing sneakers with heels (but not in a Jenny-from-the-block kind of way). That means something coming from a tall person who hits around a size 12 or 14 in clothing. Size matters when it comes to how much weight your shoes have to support. They fit a little snugly in the foot -- I wear size 8.5/9; in these I needed the 9. Bonus: the shaft of the boot is a generous fit, which will work for many women with curvy calves.

Timberland Earthkeeper Anti Fatigue Insole

The Rudstons are waterproof from top to toe, and include a lining made from recycled plastic bottles. My favourite element, however, is the pair of removeable, leather-topped Anti-Fatigue insoles. Please, Timberland, make these insoles available for sale on their own -- I take them out to put in whatever boots I'm wearing when I'm not wearing the Rudstons. Amazing. Available at Town Shoes and Browns; if you live in the US, they're on sale at

Gap Sweater Cuff Boots

If you see the Gap Sweater Cuff Boot ($82.99 on sale) in your size in a store, buy them immediately -- I snagged the last pair at the Bay/Bloor location recently. Didn't care that they were scuffed (probably why they were only $30) -- couldn't pass them up. I already have a no-longer-available black pair of ankle boots from Gap with the same pitch and sole; when worn with the genius Timberland Anti-Fatigue insoles, they're marvelously comfortable. Available via -- whoa, last pair of size 6 just went.

Gap Knit-Cuff Rainboots

Also at the Gap right now are these cute Knit-Cuff Rainboots ($54.95). If I didn't already have a great pair of knee-high black wellies from Joe Fresh, I'd buy these. Great gift -- use them as stand-up stockings you can stuff. Available via, 30% off right now.

Marks T-Max Heat socks_Roots Russian Vamp Tall Boots

I do not yet own these lovely Roots Russian Vamp Tall Boots ($288, But I have a crush. Like the Timberland Rudstons, they're waterproof from top to toe. They look great worn with the Roots Cabin Socks (if you're tall, you may want the longer versions -- called Cottage, I think, but not on the Roots website) popping up from the top. And if you want to wear them in the winter, a superwarm pair of socks such as the Marks T-Max Heat Knee Highs (above left) should keep feet and legs warm. Roots Russian Vamp boots and cabin socks available via; Marks socks via

J. Crew Booker mid-heel_Madewell Archive Boots

I hope my mother doesn't read this post because she'll be horrified at my spendy ways. (Auntie, if you read this, do not tell her about it, please!) I do happen to own these J.Crew Booker Boots (left, $348 USd), which I bought on a trip to NYC, as well as these Madewell Archive Boots (right, $298 USd), over which I obsessed for weeks until I found a way to order them from the US without strangling my wallet any further. (The 30% price difference + shipping makes these an ill-advised online purchase if you live in Canada.) Both are comfortable -- I added cushiony insoles before I met my Rudstons -- and definitely gift-worthy (the J.Crew boots fit true-to-size; the Madewell's are a titch narrow). Plus, they're available in extended calf widths for curvier legs. J.Crew boots at J.Crew at Yorkdale; Madewell boots,

crabtree and evelyn la source gel booties

At home, I'm in love with these Crabtree & Evelyn La Source Ultra Moisturizing Gel Booties($28). When my poor feet feel dry because I skipped the lotion after my morning shower, I slip these on for a while. Their gel lining is infused with shea butter, vitamin E and jojoba, olive and coconut oils, which, as feet warm up, gently soften skin. Note: the booties contain no parabens or mineral oil. And they're reuseable -- I've used mine about 10 times so far and they still do the job as well as the first time. (Just make sure feet are clean, right?) Great gift -- if the stores got more stock in time. They sold out fast pre-season. Available via Crabtree & Evelyn stores; for store locations.


And there will always be a place in my heart and in my sock drawer (and on my feet -- you get it) for the Airplus Aloe Infused Ultra Moisturizing Socks. But you can only get a full-sized pair (the socks sold on their own are smaller and shorter -- weird) when you spring for the holiday-time Airplus Spa Value Set ($12.99), which comes with pumice stone, scrub and foot cream. Worth it, though -- these socks are silky and insanely soft, different from regular chenille socks you can get at some clothing stores. Available at Shoppers Drug Mart and Zellers.

Happy holidays, happy feet. You in?