Personal Shopper: What can Ami and Laura wear with flat black knee high boots?

Ami S. wrote, "I bought these awesome boots in black (they read more weathered and dark gray than black), but now I'm stumped as to what to wear with them--besides tucking in skinny jeans. I'm a big fan of the "show-a-sock-cuff-above-the-top-of-the-boot" look, but I never know how to wear that. If you could maybe do a post as to what to wear with flat knee-high boots, that would be great!"

Then, Laura S. wrote to say, "I bought these Frye Shirley Riding Boots (picture attached) last winter. I didn't get to wear them as much as I would have liked. I meant to wear them with cute dresses or skirts. However, because of my lack of fashion sense, I'm not sure what would look the best with them. Fall is approaching; so, I'm trying to get my wardrobe prepared. Could you find some dresses or skirts that would look great with my black riding boots. Thanks, Laura"

Ami and Laura, this was interesting. The lace-up shaft and chunky sole gives Ami's boots (#1 in pic) a punkish edge, whereas Laura's are more classic in style You can always tuck 'em into skinny jeans, like you mentioned, but here are a few other options to consider: A knee-length skirt in heavy fabrics for a more traditional look, or lighter, feminine ones for a gritty-meets-pretty contrast, paired with patterned or bright tights. Alternatively, if you want to do the "show-a-sock-cuff-above-the-top-of-the-boot", try a mini skirt with the sock + boot combo, and maybe a military jacket or turtleneck. A sweater dress with leggings or tights would also be sooooo adorable! Basically, with both of these boots, the fashion world is your oyster.

Any readers have similar boots, and some outfit suggestions for Ami & Laura S.? Let us know in the comments!

1 - The Boots: Charles David 'Regiment' Lace-Up Boots ($385) and Frye Shirley Riding Boots ($398)

2 - Sparkle & Fade Heavy Knit Oversized Cinch-Waist Dress ($48)

3 - The Sweeter Sweater Dress ($60)

4 - Sparkle & Fade Full Voile Skirt ($29 on sale)

5 - Boden Stitch Detail Skirt ($68)

6 - Wet Seal Distressed Skinny Jeans ($30)

7 - Ultraviolet Tights ($18)

8 - Express Sheer Zebra Full Tights ($17)

Frustrated in your search for that perfect leather handbag, red stiletto pump, or whatever makes your heart go thump in the night? Send us a request and we might do the shopping work for you in a future Personal Shopper feature!



Posted on 08.23.10 at 7:20 AM

bonus points if you can find cheaper ($100 or under) versions of either/both boots!!! kthx :)


Posted on 08.23.10 at 11:22 AM

thanks so much!!!

Ami S.

Posted on 08.23.10 at 1:10 PM

Woo-hoo! Thank you so much! I can't wait for it to cool off so I can sport my boots and new looks!


Posted on 08.23.10 at 8:51 PM

I have those same Charles David boots! So glad to see more suggestions for how to wear those suckers.

I've been thinking about throwing on something airy and feminine to contrast the old school military aspects of the boots. Example: with black tights and long black cardigan. I love taking my summer skirts/dress and pairing them with tights/knee socks and a heavy cardigan to pull them into winter... it give me an excuse to buy more dresses.

And careful with that Voile Skirt - it's gorgeous, but the sizing runs big and I had a button fall off when I when to try it on in store :(


Posted on 08.24.10 at 4:24 PM

OOooOOoooh, Caryn, you have good taste! Thanks for the extra ideas, and the warning about the Voile skirt!

Post A Comment



If you've got a product or service that you'd like to promote on Outblush, click here to find out about our advertising opportunities.

Scroll down for more kickin' selections, and let us know what you think with our NEW Comments feature!