Have you escaped from Ugly Mom Island?

Me?  Sure.  Yes.  On most days, I feel like I’ve successfully escaped from Ugly Mom Island.  It’s not that I look runway ready all the time — on the contrary!  Sometimes when I’m talking about my book, I notice that people slowly check out what I’m wearing and a look of confusion creeps across their faces.  She wrote a fashion book?  But she’s wearing jeans and a t-shirt.  Maybe she’s suffered a recent head injury and her physical therapist suggested she write as a way of therapy, regardless of whether she’s knows the subject or not.

Style doesn’t mean you have to be fancy all the time.  It just means you have to be you.  From my style trial, I now understand what kind of jeans I should be wearing for my body type and that Hippie/Bohemian/California Casual style is the look that most closely resembles my personality.  So now when I go shopping, instead of wandering aimlessly around wondering W.T.F. I should get, I zip through racks because I know what works for me.  It feels great.  It feels really empowering.

For example, this is what I used to wear —


This is the picture from my very first day of My Year of Fabulous.  I actually miss that jacket.  I had it forever and then I was jumping on the trampoline with the kids and our dog, Jake, (not something I recommend) and he bit me and tore the sleeve off of the jacket.  I tried to sew it back on, but it’s fleece and I can’t really sew in the first place so it just looked awful and I had to throw it away.

And after my style trial, this is what I wear now —


It’s not super fancy, but it’s definitely Hippie style.  The only fancy person in this picture is actually August.  My shirt is Free People.  My boots are Uggs and very California Casual/Bohemian and of course, the aviators kind of complete the vibe.  I’m comfortable, I’m still wearing jeans, but I look more put-together than the previous picture, right?  To me, that’s the definition of escaping from Ugly Mom Island.  Going from clothes that don’t say anything about you to clothes that do.

Okay, so these are my before and after pictures.  And I’m wondering — would you be interested in sharing your before and after pictures?  We’re talking about just regular old smart phone pictures.  If you feel like you’ve escaped from Ugly Mom Island, I’d love to post your story on Riot Ranch.  If you do, not only will you become very famous on the world wide web, but you will receive a free copy of my book, Escape from Ugly Mom Island!  What could be better?  (Technically, a lot of things but let’s not get picky.)

So if you’re interested, just contact me and we’ll get started!


  • Claire says:

    Uh oh….your top outfit is my winter uniform. I looked at the picture and started checking stuff off. North Face jacket? Check. Bootcut jeans? Check. Running shoes? Check. I wear this stuff from Oct-March. I guess my excuse is that it’s so cold all the time! Even inside a house I’m freezing. I can’t seem to find cute winter stuff that really keeps me warm unless I spend gazillions of dollars on cashmere sweaters I have to have dry cleaned. Yeah….I don’t do dry cleaning. And everyone out wearing their cute leggings and tall boots? The leggings don’t keep me warm and I feel like I’d be just one of the crowd with those tall boots since EVERYONE wears them.
    I do much better in summer. Sundresses are easy. I can find cute tops and shorts and flats in cute colors.
    But winter….it’s a problem and I don’t know how to fix it. I really don’t.

    • Holly Hester says:

      Yes. Winter is hard when you need to keep warm. I especially have a hard time dressing in the winter because if it is rainy or mucky my clothes get disgusting quickly because of the whole living on a farm situation. I did stop wearing fleece jackets around and started got one of those padded patagonia jackets. They look a little dressier. Plus I got a few cashmere sweaters from thrift stores for like ten dollars and cashmere is sooooo warm. I also stopped wearing sneakers and put on boots — it really does make a difference in the whole ensemble — shoes are kind of it. It doesn’t matter what else you’re wearing if you have cute shoes on people (especially women) will just gawk over shoes! If you get a pair of skinny jeans (not leggings) and wear tall boots with those you could stay warm. My suggestion — quilted long patagonia jacket, skinny jeans, comfortable boots (a brand like merrills (very sturdy and indestructible) or frye (expensive but comfortable). If you put a thrift store cashmere sweater underneath you will definitely stay warm. Hope that helps!

  • vicki says:

    maybe you won’t hear this from many?…….i love your “after” toggs, and sure wish I could afford uggs and freepeople stuff. i’m not any good at all at thinking up outfits, but i know what i like and know it when i see it, and often get compliment on my clothes. i drool looking at uggs and freepeople stuff and dream of being able to affford them!!!

    • Holly Hester says:

      It’s funny that you say that because I think uggs and freepeople are too expensive too. I saw these uggs at Bloomingdales with my stepmother and since she’s a bloomingdales elite shopper (or some name like that), she was able to get them for me for next to nothing. And the Freepeople shirt I found at a consignment store. So both items were kind of inexpensive. Have you tried thedup.com? It’s a second hand online store and you can search for specific items — like search for Freepeople and it will all pop up!@

      • vicki says:

        yeah!!!!! i’m a bigger fan now!!! no, haven’t tried that place online but will check it….but consignment shop’s are my thing. i also shop forever 21 and the jr shop’s of department stores because i’m blessed to be able to fit into some of their clothes and they are soooo much less expensive than shopping where most women my age (63) shop. it’s always great to have a pal or relative with a discount somewhere…ha!
        i find a lot of good stuff at our local goodwill and salvation army stores also, and a newer large place called “community aid”….it’s crazy, can find things with tags still on that no one ever even wore.

        • Holly Hester says:

          Yes, forever 21 has amazing prices. Once I walked through that store on my way to another store and ended up in there for like an hour. And community aid — that sounds amazing!

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