Ashley (above) illustrated by Kayci Wheatley. 

About Ashley Judge

Ashley is just a girl … standing in front of a boy … asking him to love her. Oh wait, that’s somebody else. 

Ashley Judge is the head gal at AlwaysFits.com, a unique online shop, known for its nostalgic, sweary, feminist gifts. Ashley turned a lifelong love of curating treasures into a multimillion dollar business.

AlwaysFits.com is approaching its 10th anniversary, under Ashley’s creative and strategic direction. AlwaysFits.com has been mentioned on The Today Show, as well as in Vanity Fair, Better Homes & Gardens, Elle, Redbook, Cosmopolitan, Good Housekeeping, HGTV, Harper’s Bazaar, Women’s Health, Scary Mommy and hundreds of other national publications. 

Ashley loves the Golden Girls, feminism, tragically lame soft rock, Bev from The Goldbergs, self-deprecating humor, Ruth Bader Ginsburg, alliteration, and her 6 year old daughter - but not necessarily in that order.

Previous to starting her own company in 2009, Ashley worked for Ambassador Swanee Hunt, planning political events, and as director of hotel logistics for the 2004 Kerry/Edwards presidential campaign.

Ashley (above), surrounded by her favorite AlwaysFits.com goodies! Illustrated by Jade Butler. 

#TBT

In 2012, Ashley shared some business lessons with American Express. To read that article, click here. 

Check out this 2009 Patriot Ledger feature about Ashley and her first company, Tra Tutti.



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