7 Outfit Ideas To Make Your Most Boring Clothes Feel New Again

1. Cut your pants.

Cuffed pants are about as relevant as Justin Jeffre from 98 Degrees. “…Come again?” you’re probably thinking to yourself right now, and you would do well to think this too! Because that is precisely my point. Even Google’s search engine knows how irrelevant Jeffre is:

It’s just time we all, collectively, take our cuffed pants and un-cuff those bad boys. I know this isn’t easy — trust me, I know the urge to cuff a pant — but I’ve found an alternative that’s far superior: cut them. Yes, you could get them professionally hemmed, but then that would eliminate the prospect of a raw, frayed look at the bottom of your pants like this:

2. Put a skirt on it.

It’s sort of like, in Portlanida, when Fred and Carrie suggested we “put a bird on it.” Except in this case, it’s a skirt.

I really love how Shannan Elinor Smith styled this look here for the Opening Ceremony blog (assisted by Rika Nurrahmah). In the photo below you’ll find, not one, but two skirts — an orange, Full Court skirt, worn under a clear Fleamadonna skirt with lace trimming.

You might also want to put a skirt on it, if “it” means an uncomfortably small dress. At left, you’ll notice an awesome dress that’s just too damn short on me; at right, a skirt thrown over the dress. (Note: a good marker for a dress that’s “too short” is if your actual butt touches the subway seat when you sit down.)

3. Wear a shirt under your boring black dress.

My requisite little black dress is velvet, pretty tiny, and made by Veda. There’s nothing wrong with it; it’s been a loyal confidante during our five years together. But like a lot of relatively plain, short black dresses, it just grew stale. Then I threw a shirt on underneath it and thought: hold up — I think I’ve still got it! (re: below.)

4. Dress it down.

Another problem with having an item of clothing for over five years is that, during those five years, your style may have changed. For instance, where heels were once a staple in my wardrobe, they’re now one of three things I’m deathly allergic to. I’ve been called a “little man” before, but I still think a pair of sneakers or loafers will look cute with almost anything.

5. Turn a dress into outerwear.

When I was younger, my style tended towards trashy. It left me with a surplus of dresses I had no clue what to do with — the ones that salaciously zip- or button-down the front. But that was all before I learned their dual purpose as really cute overcoats. Et voilà.

6. Throw a shirt over a dress.

Hey, who here is addicted to eBay?? No one? Great! (An aside: this is probably as good a time as any to plug my eBay personal shopping skills. If you should find yourself needing a personal shopper, but can’t be bothered with getting off of your couch, PM me.) This habit of mine has helped facilitate some of the most unnecessary purchases in history. For instance, this Proenza Schouler dress. It’s stunning, but I just haven’t yet stumbled on an opportunity to wear a tube-bustier dress. Put differently: the bar mitzvah years are over. And so, in trying to dress it down, I discovered the ol’ shirt-over-the-dress hack.

7. Wear your pajamas outside.

I like my bare ass to be touching silk at all times; because of this, I usually end up spending as much time as humanly possible in my silk robe. Which is how I learned that a robe makes a great jacket too.