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How to Keep Your Shirt From Coming Untucked

There's more than one way to pin this donkey (or shirt).

In our latest column, "Ask a Fashionista," you can solicit our strongly held opinions on everything from how to wear a midi skirt without looking like a tree stump to whether a certain retail CEO should go ahead and resign already.

Q: My go-to outfit is a button-down silk shirt half-tucked in front and a skirt or jeans, but my shirt is always coming untucked and looks messy. Is there anything I can do to keep it in place? - Courtney, Washington, D.C.

Ah, the perpetually un-tucking tucked shirt. Anyone who wears her skirts or pants between her natural waist and her hip bones likely has to combat rotating garments and shirts that billow up or come completely untucked. Fortunately, there are solutions.

1. Tailor your pants and skirts so they fit snugly on your natural waist or hip bones.

Shirts tend to come untucked or billow up because the waistband on your skirt or pants is too loose, which allows for a shirt to come untucked because a) there's a large gap and/or b) because the waistband of your skirt or pants is sliding up and down. If that's the case, get thee to a tailor. (Seriously, it's about the best thing you can do for your appearance besides sleep -- and if you don't believe me, take it from Jennifer Aniston, who even tailors her t-shirts.) Your skirts will best stay put if you tailor them to cinch at your natural waist and graduate out towards your hips; rectangular or tubed-shaped skirts will simply ride up and down. Trousers and jeans you'll want to tailor at your natural waist (if they're high-waisted) or your hips (if they are mid/low) -- a belt will keep them extra snug.

2. Add or seek out elastic waists.

Pants and skirts with firm elastic waists also keep shirts in place, and you may want to talk to your tailor about putting an elastic band in the back of some of your favorite pairs. Some designers already incorporate this into their designs -- I recently tried out a sample from Spanx's new line of jeans, which have elastic to prevent gapping in the back. They're the first jeans I haven't had to tailor to sit snugly on my hips -- great for keeping my shirts in place!

3. Tuck or pin your shirt into your underwear, tights or shapewear.

If the waistband of your jeans or skirts simply isn't doing the trick (or if you've lost a little weight and it's suddenly loose), you can layer something stretchy underneath to hold the ends of your shirt in place. Tights work well, as does shapewear. In a pinch, you can tuck your skirt into the edges of your underwear, or pin it with a safety pin. The former will work better with something that has a firm stretch -- a lycra or spandex-blend seamless bikini or thong from Victoria's Secret, for example, will be more effective than a cotton panty with a gentle lace waistband. If your shirt is long enough, I recommend smoothing your shirt over the front of your underwear and tucking it in at the legs, rather than tucking it in the waistband -- it'll lay more smoothly.

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4. Tape your shirt to your pants and skirts.

Despite all my talk about "anchor points," I still prefer to wear skirts that sit at my hip bones or just above (mostly because I have a short waist). Sliding and billowing, therefore, is inevitable -- or was, until I found fashion tape. If my shirt is just tucked in front, I'll take two small pieces of double-sided clothing tape (I use this), fix them to the front of my skirt, and attach my shirt. The shirt then stays in place all day. Unfortunately, the tape will only work with smooth fabrics, like cotton, silk and fine wool; nubbier wools and knits won't stick together, in which case I live and let untuck. You could also use safety pins.

5. Wear a bodysuit.

Donna Karan designed bodysuits specifically to keep shirts in place. Victoria's Secret has some good, more affordable options too.

BONUS TIP: How to do a good tuck.

While researching this piece, I sent an email to Man Repeller's Leandra Medine inquiring about her techniques for keeping her shirt in place. She doesn't use tape or pins, but she does have a tucking technique that makes for a neater look.

Here's how it works: Let your shirt hang flat in front of your trousers, then fold the bottom half of your shirt underneath, and tuck it into your waistband. (You can see it in action on Medine here.)

I tried it earlier this week, and liked the look -- doubling up the shirt fabric at the bottom made the front of my shirt lay more flat. The only downside is that, without tape, my shirt was more likely to come fully untucked, so I'd still recommend combining the folding and taping technique.

Birchbox also has a good video tutorial (for men, but no matter) on how to create a crisply tucked shirt. The key here is folding the sides along the seam for a tighter fit. Check it out below, and please share any tips you have for keeping a tucked shirt in place in the comments section below.