Help me be Stylish: What do I wear with leggings? Edition

First of all, thank you for de-lurking or re-lurking or just lurking around in general on my last post. You made me so thirsty with all the drinks, I had to try one of each of them. Then I passed out drunk and now that I’ve resurfaced, I have another fashion emergency (or two) for you to handle. (Aren’t you glad you come visit my site? I’m always putting you to work! One day I’ll repay the favor, promise.)

Here’s the back-story: Up until about four months ago, I had a full time office job in San Diego. This means I wore high-heels for at least forty hours out of my week and if I wasn’t wearing wedges or high-heeled sandals when I went out, I was rocking the flip-flops.

Now I’m living in Northern California, where it’s significantly colder in the autumn/wintertime (what are these seasons you speak of? I haven’t seen leaves change color in five years, what a concept!) and it rains. A lot more. So, needless to say, flip-flops are out of the question and since I don’t have an office job at the present time, most of my work is done in fuzzy socks (which means all my lovely high-heels are currently gathering dust in my closet, SAD FACE.)

So! What does this all mean, you ask? Well, it means that other than running shoes or UGGS, I have no casual flat shoe options. And, as much as I love my UGGS, I just don’t think they’re necessarily appropriate for going out. Case in point, here’s what I managed to throw together to grab dinner last night. It’s not BAD, but it’s not good either, am I right?
Help me be stylish - Flat shoes & Leggings Related: After you all weighed in on this Help me be Stylish post, I went out and bought both skinny jeans (which unfortunately aren’t “skinny” enough, ARGH) and leggings. Ahh, leggings, how I love thee. So slimming! So boot-friendly! So much like yoga pants! But the question is, what kind of top do I wear with leggings? I threw that chunky grey sweater over the ensemble and I think it looks…Okay…But it’s definitely not the look I’m really going for. I’d like something a little more, umm, streamlined.

Alright, you have your assignments: Flat shoes and legging tops. Now, HEEEEELP!

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8 Responses to Help me be Stylish: What do I wear with leggings? Edition

  1. akymbo says:

    As super-uncomfortable as they often are, ballet flats are my number one choice after boots when it comes to leggings/skinny jeans. Or if I’m going more casual, Converse.

  2. Yeah I totally agree with you about Old Navy jeans not being skinny enough to wear with boots … I’m a fan of Gap’s Always Skinny jeans & BDG jeans from Urban Outfitters. And flats are easy … all I wear are flats! I just buy whatever I think is cute from Target or Payless or Old Navy or sometime Urban!

  3. Aunt Rach says:

    Try a tunic–very flattering & made to be worn w/ leggings. go online 2 check out some different styles. it’s now become a classic, really. tori burch brought the style back & made it cool again…u can find hers @ nordstrom rack or loeman’s for drastically reduced prices. Of course, you can always wear a juicy dress over them!

  4. Raven says:

    Definitely GAP Always Skinny. I am insanely in love with them and wasn’t happy with the Old Navy skinnies.

    Shoes: Ballet flats or knee high boots.

    Tops: tunics or dresses. Occasionally I will toss on an oversized sweater, but I think that looks better with jeans.

  5. Emily says:

    I picked up a SUHWEET pair of Steve Madden boots from DSW this winter… and I LOVE them. They are flat and the perfect shade of brown so I can wear them with any color practically … including black leggings and yellow tights!

    I buy my skinny jeans from Charlotte Russe for like $29 or something ridiculously cheap. I heart them.

    i’m still trying to figure out the whole “perfect shirt to wear with leggings” thing. So far, I’ve got two long grey sweaters and that’s about it. Every now and then I try and pair a dress with them .. but it just doesn’t work out in the end.

  6. Sarah says:

    Wow, you guys are awesome, thank you!

    I guess I just need to suck it up and buy the GAP skinnies, huh?

    As for flats, I just really, really, really have a strong aversion to ballet flats, so flat boots might be the way to go.

    Tunic, good idea, but I don’t think I can wear that in the winter. At least, not in the winter HERE, where I live. I’d freeze!

  7. Chels says:

    You definitely need a pair of tall leather boots, girl! Perfect for the Northern Cal weather. That outfit would be fine minus the uggs! A sweater dress, a shirt dress, OR a long cardigan (LOVE cardigans) with a nice belt around the waist would work, too.

    I also agree about the Gap 1969 skinny jeans. They’re fabulously fitting and affordable (compared to pricey designer denim!)

    HUE makes great leggings, too, if you’re looking for more. Tons of colors, patterns, and thicknesses!

    Hope that’s helpful! 🙂

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