Fall/Winter 2008’s Best Boots Under $100

November 11th, 2008

No piece of footwear epitomizes daytime chic quite like the boot.  And Fall/Winter 2008 has welcomed a number of sophisticated boot trends: ankle boots, buckled boots, fur lined boots, cuffed boots, and slouch boots, to name a few.  We’ve rounded up our favorite picks for each of these boot trends - each one priced well under $100.

Ankle Boots
Tate Oxford Bootie
Tate Oxford Bootie | $29.99 at Payless
Oxfords lend a tailored twist to the boot silhouette of the season: booties.  

Buckled Boots
Mossimo Kiley Boots
Mossimo Kiley Boots | $29.99 at Target
Buckles add a tough girl vibe to these chic grey boots.  Love the ever-so-slight slouch to them–and the very wearable 2.5" heel.

Faux Fur Lined Boots
American Eagle Mallory Boot
American Eagle Mallory Boot | $44.99 at Payless
Looking for a cold-weather boot that’s as cute as it is chic?  Found it.  The fur lining provides instant chic, while the pom poms give these boots an air of lightness.

Cuffed Boots
Zahara Sweater Cuff Jersey Lined Rain Boots
Zahara Sweater Cuff Jersey Lined Rain Boots | $29.99 at Target
Keep your feet nice and cozy on the rainiest of days with a pair of sweater cuffed rainboots.

Slouchy Boots
Slouch Boot
Slouch Boot | $79.99 at Cathy Jean
Be one with the inevitable slouch when you slip on these sophisticated boots.  Perfect for layering under jeans - or for pairing with a chic sweaterdress.

Entry Filed under: Shopping Guide,Trendscape,Women

19 Comments Add your own

  • 1. Lynn  |  November 11th, 2008 at 7:04 am

    OK, Trish, these are ADORABLE and make me want to blow my entire paycheck on boots.

    But my problem is what to wear them with when I get them home. You talked about the slouch boot, but what about the ankle boot and the buckled grey ones or the fur boots? What’s best for those? I know they can be worn under slacks/jeans, but who wants to hide them all the time? :)

  • 2. Trisha  |  November 11th, 2008 at 10:11 am

    Hi Lynn,

    Great question, and I’ll have to do some Ready Made Outfits to illustrate how you can wear these boots with skirts/dresses. In a nutshell, though:

    Ankle Boots: You can wear these with skirts and dresses–really! For the longest, leanest look, wear them with a pair of dark colored tights. Instant chic, and it’ll streamline your legs.

    Buckled Boot: I really like these paired with something super feminine for contrast. Try a purple dress–or a ruffled blouse and skirt.

    Fur Boots: Sometimes you’ll be able to tuck a slim fit jean into boots like these–the look is very celebrity-at-Sundance (and indeed, it would be warm enough for Utah in the winter with the right socks and long underwear). But you can wear this boot with a dress or skirt in a daytime fabric (e.g. no sequins or shine). A fair isle sweater with a skirt would be lovely.

    Hope that helps, Lynn!


  • 3. anu  |  November 11th, 2008 at 11:43 pm

    hi trisha,
    these boots are really cool! could you post some recos for tall boots too, please? i am trying to decide whether i should go in for one of these or hold out for a tall one.

  • 4. Trisha  |  November 12th, 2008 at 11:01 pm

    Hi Anu,

    How tall are you looking for? Knee high, or over the knee?


  • 5. Ashley  |  November 13th, 2008 at 9:10 pm

    The boots looked really cute, but the slouchy boots and the faux fur ones definitely looked as cheap as their retail price. Gojane.com has some cute options this season, as does forever21.com and occasionally Aldo.com

  • 6. Trisha  |  November 14th, 2008 at 12:40 am

    Thanks for the tips to check out Go Jane, Forever 21, and Aldo, Ashley!

  • 7. Key Wii  |  December 13th, 2008 at 4:13 pm

    I [heart] these boots so much. I really wanted a pair of ankle boots, but they’re pretty pricey. So thanks :)

  • 8. Marie  |  December 30th, 2008 at 11:23 pm

    i LOVED these booties, and when i went out looking for them, i found these http://shop.nordstrom.com/S/2982277?Category=&Search=True&SearchType=guidednav&keyword=peep+toe+in+All+Categories+%3E+Black&origin=searchresults and thought they were super cute; but since they’re slingbacks, i can’t really figure out what to wear them with. can i wear them just like the regular oxford booties?

  • 9. victoria  |  February 7th, 2009 at 12:21 pm

    I love the Women’s Zahara Sweater Cuff Jersey-Lined Rain Boots!!! they are soo cuite!! geting them 2 day

  • 10. Jenna  |  February 27th, 2009 at 12:02 pm

    I love the little clutch purse. Very Balenciaga looking.

  • 11. Hailey  |  October 21st, 2009 at 5:24 pm

    Thanks, Trisha! I LOVE the slouchy boot. Hah. A bit expensive, though…

  • 12. gigi  |  December 5th, 2009 at 10:40 am


  • 13. Anonymous  |  December 15th, 2009 at 6:43 am

    I love the chic mallory boot but i cant find it anywhere

  • 14. Rachael  |  December 15th, 2009 at 6:46 am

    Hey I love the chic Mallory Boots but I can’t find them anywhere! Can you help me plez! all payless shoes show that they are all gone,do you know anywhere else they may have them?

  • 15. kay  |  December 17th, 2009 at 8:12 pm

    Went to payless to purchase the mallony boot,, they were out. I have tried to find them every where, no luck.

  • 16. aimz  |  December 21st, 2009 at 5:22 pm

    I have those ankle boots from Payless. I Love them. I actually wear them with jeans to work or a night out… really dresses them up.

  • 17. Gail  |  December 27th, 2009 at 11:59 am

    I bought a pair of the Mallory boots but needed a bigger size went back no luck where can I find them or order them on line I really love them

  • 18. mallory  |  June 2nd, 2010 at 6:49 pm

    I have the booties from Payless and I get compliments every time I wear them :)

  • 19. emily  |  September 27th, 2012 at 1:53 pm


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