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You just spent some good money on some riding boots and want to wear them to death because, well…you spent good money!
Riding boots are meant to be worn outside your pants so wearing the skinny versions of pants are the way to go. When you wear skinny on bottom, it’s best to add volume on top. Here are a couple of ideas for outfits if you are in your 20’s or early 30’s for making those boots do the walking.
Left Outfit:
We did not make this up but pairing the Vince Riding Pant
with your riding boots sounds like a match made in heaven. (or hell if you hate your thighs) This outfit looks good on the long and lean. Wear a neutral scoop-neck tee under this fitted camel double-serge jacket. It has some great details in the back and comes in Petite and Tall. Now, add a great plaid scarf
and you’re ready to take on the day.
Right Outfit:
I love the look of skinny jeans and boots with a big tunic (check out this sweater tunic
for inspiration) or shirtdress and vest. This Alexander Wang Vest Shirtdress does the trick and when you balance the proportions with a long colorful necklace, you have a pretty fun outfit that can work for going out or the weekend. There are lots of fun vests out there so get a few and mix and match them with your tunics and bigger shirts to create different looks. Add the Sak Crossbody 
in patent gray so that your hands are free to push away the boys.
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October 30th, 2008 at 3:32 am
Does the boots over jeans style work only for 20-30 year olds?
October 30th, 2008 at 4:17 am
Well,..that’s fine…but what about those over their mid 30’s..???? are the riding boots not age appropiate???!?..Hmmmm. ..I(41!:-(()love to wear them a lot!!!Basically with dark monochrome printed flowy calf/knee length chiffon skirts-or plain dark A line corduroy and jean skirts. But love them with dark brown wrapdresses, or dark (black/brown/indigo)7/8 cuffed trousers/jean, too(more age appropiete than to tuck in!)…Just for your refference, mine are a sort of very dark brown coloured (meant, the boots..:-)
October 30th, 2008 at 4:21 am
Beg your pardon, I’ve meant 2x”appropriate”, of course…:-)
October 30th, 2008 at 8:54 am
The boots are fine for all ages. And boots over jeans too!! But, the entire outfits don’t work for late-30’s and on because the one with the slim jacket is with leggings and the other is with a trendy top and vest. I’m not averse to gals at any age wearing the skinny jeans as long as they can pull them off. Anything that is too trendy (leggings, little vests and big tops) look like we’re trying too hard so that’s why I mentioned the age-appropriateness of the outfits.
October 30th, 2008 at 11:44 am
I am 43 and stand 5′6″ and weigh 125 pounds - I would wear either one of these outfits. It isn’t like a whole lot of skin is showing. I would however, remove the bubble gum size beads and bag from the outfit on the right. Perhaps a skinny multicolored scarf and leather bag.
October 30th, 2008 at 3:12 pm
Would love to see the boot over jeans done with tops that would be
less trendy and for other age groups.
November 2nd, 2008 at 7:13 am
Yes, please show some choices for the 40’s set!
November 17th, 2008 at 10:19 am
I’m really struggling with this. I want to wear the boots over my jeans, but trying to do it in an age-appropriate way. And I am not one to wear voluminous tops b/c of my chest. I feel I’m better in tailored pieces. I usually wear cashmere sweaters in the winter.