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What Do You Wear with a Maxi Skirt?

I bought a pink ballet maxi skirt the other day. I had to think twice, even with a 25% off coupon in hand, but I love it. It’s so feminine! It’s so beautiful! It’s so impractical!

If I have to bend over to pick something up (say, I don’t know, a child or two), the skirt touches the ground. Fine in a dressing room, not so great when out and about. Yet I still love it.

The skirt nearly grazes the floor if I wear flats, so heels or wedges are a good idea with it. And I kind of have no idea what to wear on top, because I haven’t worn a maxi skirt since I was a teenage goth (and duh, you just wore a black band tee with your black skirt back then). The shirt I tried on with it looks good, but the skirt needs to have more than one partner. I like my clothes to be polyamorous.

Hey there, black and white striped sweater that I saw in the window of J.Crew (and that I can’t afford). I feel like you would go nicely. I want this whole look, actually.

Now that I see how much I like the longer skirt length on me, I’d wear this dress too, but the ballet maxi is the only big clothing purchase for me right now. I know I can find another striped top to wear with the skirt, and a white cotton tee in the right cut would look fantastic too.

It’s times like these that I wish I kept up with fashion blogs and glossies, because I’m sure I’d have a million more ideas. I know the maxi skirt trend has been going strong for a while and I’m just jumping on board now, so any tips?

Style: With a Polka Dot Top

My outfit was a last minute switcheroo, but I like it even more than the original one I was going to share.

The sheer pink polka dot tights I had based my whole other look around ripped. And not just a little rip that I could have fixed in Photoshop, I’m talking about the kind of rip that essentially turned my tights into cutoffs. So I grabbed a polka dot shirt instead. I just wish I had realized that I also grabbed the same skirt I showed last month. Oh well. I suppose the lesson here is that a white pencil skirt is more of a wardrobe staple than you might at first think.

Here’s how to get the look:

  1. Gingham Pendants

  2. Dolman-Sleeve Top

  3. No. 2 Pencil Skirt

  4. Sinclair Glasses

  5. Swing Bag

  6. Ambitious Heels

A note on some of the items I’m wearing that are no longer available: As I mentioned last time, my skirt is seven or eight years old. I’ve had the shoes for just as long, and I bought the bag in 2008. Actually, I featured it in my first ever style post, and suddenly it’s on trend! My sister keeps begging for it when I “get sick of it” and I keep telling her it’s not gonna happen. And I’ve featured the necklace before as well. I scooped it up at 75% off when it went on clearance.

Style: With a Polka Dot Top

Style: March ’12

Well. Yesterday was hard. Let’s have something a bit lighter today, hmmm?

I approach these style posts in one of two ways. I either start with some beautiful item, like a dress, and build a look around it, or I recreate an outfit I already own. Here are some items that are similar to what I’m wearing, and I’ll explain my thought process a little more below.


  1. Gramercy Grand Watch

  2. Baripada Necklace

  3. Pink & White Striped Tee

  4. Ampersand Gold Ring

  5. White Skirt

  6. Harlequin Sweetie

  7. Regina Wedges

  8. Hooverville Burgundy Glasses

(Eleanor ran in on my photo shoot setup, and I thought she looked so cute. Toddler photo bomb!)

My outfit above was a mix of new and old, but mostly old. I picked up the necklace before Alt Summit to wear while speaking on my panel. The shoes are new, and they will see me through to the fall, but the skirt I’m wearing is seven or eight years old, the watch is three, and I showed the bag last year when I bought it on sale.

Some of the similar items on my board above are more expensive (like the skirt) and some are less (like the top). Budgets vary from person to person, and while I’m not putting Louboutin wedges in my posts, the Regina wedges I did include may still be too pricey for some. I chose them because I have found that I usually regret cheapie shoe purchases, and I’d rather have one good pair that will last. If you’ve had better luck than I have with inexpensive shoes, feel free to sub. Same thing with the watch. I bought mine shortly after Eleanor was born, probably for around $70, but I showed the Kate Spade Gramercy above because it’s beautiful and it’s the type of watch I have: gold, oversized, with a similar band. Perhaps you already own one like it, too.

Putting a little effort and thought into the way I get dressed makes me feel better, and putting style posts together is fun. Thanks for letting me share them with you! Hopefully I’ve explained the thought behind them, but I’d love to hear what you think.

Style: March ’12

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