Three Ways to Wear Riding Boots Without Skinny Jeans

You Pick Wednesday

Riding boots and skinny jeans go together like chocolate and peanut butter.   Like butter and popcorn.  Like Thanksgiving and mashed potatoes.  Seriously, it’s not Thanksgiving if there are no mashed potatoes.  But I digress.

Outfits with riding boots and skinny jeans


Riding boots and skinny jeans were made for one another.  Or, at the very least, riding boots and skinny pants.  I mean, just look at how they were designed to be worn.

Original riding boots

Source: Pinterest

However, it has come to my attention that there are people who would love to add some riding boots to their closets but who aren’t comfortable with the whole skinny jeans or pants idea.  While I could do a whole post about why skinny pants aren’t necessarily evil, instead I decided to share with you some alternate ways to work riding boots into your wardrobe so you can wear riding boots without skinny jeans.  Thanks in advance to Pinterest & Polyvore which made my job a lot easier.

Way #1 Leggings and Riding Boots

Riding boots with leggings outfits


Yes, yes, I know that leggings are essentially just another form of skinny jeans or pants, but some people might find them more comfortable since they are designed to be worn with oversized, long tops.  In fact, leggings are NOT pants and shouldn’t be worn with anything that doesn’t cover your derriere.

Way #2 Skirts and Riding Boots

Riding boots and skirts outfits


If leggings aren’t your thing, about how a skirt or a dress with riding boots?  The key is to match the style of the boot to the style of your outfit. A more casual outfit?  Go with a more casual boot.  A dressier outfit?  A dressier boot, of course. The smoother the leather and the fewer the embellishments typically the dressier the boot will look.   At least, to my eye.  Tights or no tights, the choice is yours.

Way #3 Riding Boots under Pants

Riding boots with flared leg pants


Finally, you can wear your riding boots under a pair of bootcut or flared leg pants or jeans.  Why would you do this and hide any fun embellishments on your boots?  Well, in Chicago it can be an additional barrier against the cold and the wind in the winter.  Also, if you keep the embellishments on the boots (buckles, etc) closer to the ankle then people will get a glimpse of it as you walk or when you sit.  Make sure the boots have a slight heel as well to keep the look lean.

And there you have it.  Three ways to wear riding boots that don’t involve skinny jeans.  Although, if you aren’t afraid of skinny jeans, I have two looks coming up for you tomorrow and Friday that involve riding boots and skinny jeans.  I’m off work for the holiday so you’ll get to enjoy some of my more casual outfits for a change.


15 replies on “Three Ways to Wear Riding Boots Without Skinny Jeans

  1. Bethany @ Accidental Intentions

    “In fact, leggings are NOT pants and shouldn’t be worn with anything that doesn’t cover your derriere.”

    I would very much like to print this sentence off in 1000 pt. font, take posters of it back to my college campus, and hang them on every surface I can find, especially surfaces near sorority houses, as this important rule of fashion seems to be irrelevant to many Greek Life women at my alma mater. Eeesh. Thank you for affirming my belief that leggings are not pants.

    1. Erin @ Loop Looks Post author

      I think the only time leggings can be worn sans covered bottom is when A. Running B. Doing Yoga. Otherwise, cover your rear! Also, when wearing a short skirt make sure your leggings aren’t see thru! I just walked behind a girl earlier this week who was wearing a super short skirt and her tights/leggings had a huge hole in them!

  2. JTwisdom

    I am going to attempt to buy some skinny jeans but making sure that I wear a long jacket or sweater to elongate. Skinny jeans look so good with riding boots. I also like to the knee or 21 inch skirts with riding boots and bright colored tights.

    1. Erin @ Loop Looks Post author

      Skinny jeans and a blazer with riding boots are a great combination that just about anyone can pull off. But, you’re right in that they also look great with skirts!

  3. kilax

    Ha! Should I forward the legging part to my crazy coworker? Sigh… 😉

    I was thinking about tan (camel) riding boots the other day. My boots are black. Can you do a post on when to wear what color of boots? Or would that be too pointless? 🙂 Oooo… purple boots?!

    1. Erin @ Loop Looks Post author

      It’s funny, most of the outfits I found via Pinterest or Polyvore had brown boots with them. I suppose it just depends on what kind of look you’re going for. If you want the boots to be a focal point then I would go with brown. If you want them to blend in then wear black on black.

  4. Emily

    Yay! Thanks so much for this post! I am now on the hunt for outfits to wear with my new riding boots so I am super excited to give some of these ideas a go. I have been adamantly opposed to skinny jeans since they day they became popular… but I just caved in and bought a pair, solely to wear with the boots. Here we go!

  5. Matt

    Guy’s perspective: I think riding boots are incredibly sexy on a woman and I actually prefer the look of when women wear them with dresses/skirts (especially knee-length and shorter) instead of with skinny jeans, because with skirts/dresses, it shows off the boots and the legs of the girl wearing them. Pants and long dresses draw attention away from the boots.

    Although I do understand the practicality of #3 for colder climates (USDA growing zone 7 and lower) since I wouldn’t want some poor girl to freeze her legs off just to show off her riding boots.

  6. Pingback: 10 Step Guide to Buying Riding Boots - Loop Looks

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