These Boots are Made for Showing Off

June 10, 2014 2:59 PM

I love cowboy boots, and on a recent trip to Portland let my lust overcome me and bought some. I'm normally a conservative dresser (suits, dresses, skirts with jackets) during the week, and a jeans and Tshirt kind of person on weekends. Suggestions on what to wear with the new boots? They are mid-calf. One pair are a gorgeous rich brown with tooled roses and the other is brown and black tooling.
posted by bearwife to Clothing, Beauty, & Fashion (16 answers total)

Best answer: Are you comfortable getting some cute, casual dresses to go with the boots for weekend wear? Some of my friends have this as a staple of their wardrobe and look really cool and comfortable in it.

Tips here, and you can also find some Pinterest sites that have pinned similar styles...
posted by TwoStride at 3:05 PM on June 10, 2014 [1 favorite]

Best answer: I had a pair of cowboy boots for a while. I tended to pair them with skirts and tights. My pair was black, and with black tights and a skirt in a sedate color, they didn't look too Grand Ole Opry for my NYC life.

You can also tuck skinny jeans into them, but I think that look is a smidge dated.
posted by Sara C. at 3:13 PM on June 10, 2014

Best answer: Also, bootcut jeans. I know I am the lone defender of the bootcut jeans, but they work with, uh, boots.
posted by ablazingsaddle at 3:28 PM on June 10, 2014 [8 favorites]

Response by poster: I love bootcut jeans too.
posted by bearwife at 3:30 PM on June 10, 2014 [4 favorites]

Yeah, it being 2014 I would probably err on the side of bootcut jeans with cowboy boots (untucked, of course) rather than skinnies tucked in. It's not the most on-trend thing ever, but it's a specific look and the authentic choice for wearing cowboy boots.

Keep in mind that by pairing jeans and cowboy boots, you are definitely going to have a cowgirl aesthetic going on. It's not a neutral look.
posted by Sara C. at 3:33 PM on June 10, 2014

Can you post photos of the boots in question? Ropers are going to call for a different style than, say riding boots. Do they round toes, square toes, pointy toes? How tall are the heels?
posted by Beti at 3:49 PM on June 10, 2014

Best answer: What about brown leggings in the boots with a solid-color dress (knee-length or just above the knee) on top? Cowboy boots can awkwardly cut your leg in half but adding the leggings can unify the leg again.
posted by rogerrogerwhatsyourrvectorvicto at 3:55 PM on June 10, 2014

Response by poster: They are pointy toes. Not super tall heels -- maybe 2 inches. Kinda like these (a shot taken of a row of boots at the store, Portland Outdoor store.) They are at home and I am not so can't provide a picture right now.
posted by bearwife at 4:01 PM on June 10, 2014

Best answer: What happens if you take your work dresses and skirts and pull on your boots? Might look cute for the weekend and going out!
posted by bluedaisy at 5:29 PM on June 10, 2014 [1 favorite]

Response by poster: Here are some shots of the boots.
posted by bearwife at 9:05 PM on June 10, 2014

Best answer: Great boots. I can see why you caved. Maybe something like this for the brown ones. And maybe something a little more lacy for the roses.

I have gigundo calves and can't wear boots so I'm totally jealous.
posted by Beti at 12:35 AM on June 11, 2014

Best answer: I love the look of a cute dress or skirt with cowgirl boots, with or without tights. You might feel awkward at 1st, but I think you'll get lots of encouraging compliments.
posted by theora55 at 7:28 AM on June 11, 2014

Best answer: Yet another vote for cute dresses. Especially flowered ones look awesome with cowboy boots.

I know a woman who has a pretty great pair of cowboy boots, and she's worn them as part of assemblages that would probably look odd on a lot of people, but she pulls it off. So really I think it has to do with confidence and individual style.
posted by mermaidcafe at 8:26 AM on June 11, 2014

Response by poster: Thanks for the many wonderful answers.

For the outfits without tights . . . what does one wear on one's feet under the boots? Shortish knee socks or light ankle socks? These are comfy boots but I don't want to wear them barefooted.
posted by bearwife at 9:48 AM on June 11, 2014 [1 favorite]

Best answer: I've seen them worn with socks showing so you could try that with whatever outfit. I'd at least wear something more than ankle socks until they get broken in - unless they fit your calves just right and/or are pretty soft leather and/or a really smooth finish inside, I could see how your skin could get abraded pretty easily, especially in warmer weather.
posted by Beti at 4:39 PM on June 11, 2014

Best answer: Yeah, you're definitely going to want socks. Please trust me when I say that you should never, ever put your bare feet into cowboy boots. Unless you want to be wearing them for the rest of your life.

I think crew or trouser length socks would be fine.
posted by Sara C. at 6:49 PM on June 11, 2014 [1 favorite]