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Ask Avery: Stealing from the boys

Photo courtesy of Flickr / CHRISTOPHER MACSURAK

blog by Avery Hartmans  • 

Dear Avery,
My boyfriend has a great wardrobe and I want to steal some stuff from it, but would that be weird? Is everyone going to be able to tell I’m wearing men’s clothes? Give me some tips for how to shop in the boys’ department.

The men’s section is, most times, my favorite place to shop, so I’m more than happy to oblige. To answer your first concern, no, it is not weird to steal stuff from your boyfriend. Half the reason we get boyfriends is to steal their clothes. As long as you have his blessing (and in most cases, even if you don’t), get your thieving — yet super-chic — paws on his cool clothes.

There are a few items you shouldn’t even try to make work for you. Shorts and pants are a big no-no and will give you away immediately as the menswear thief you are. In case you haven’t noticed, men are shaped completely different from us in the sense that they don’t have hips. Any pants or shorts made for a guy are going to look baggy and shapeless on a woman, so don’t even bother trying. Men may be able to wear women’s jeans — not that I condone it — but this isn’t a two way street.

Now that we’ve agreed you should by your own pants, let’s move on to tops. Here is where I let you off the leash and give you free reign of the men’s department. Nothing is off limits — sweaters, t-shirts, button-downs and jackets can all be styled to look just as fabulous (let’s be real here: more fabulous) on you as they do on a guy. But it seems like you still need a little guidance on what to look for, so I’ll break it down for you.


Anytime I’m in a store that caters to both men and women, I peruse the men’s t-shirts. There’s nothing I hate more than a fitted, cap-sleeved women’s tee: it’s tight in all the worst places, shows off way too much upper arm and is generally uncomfortable for me. Men’s tees, on the other hand, have longer sleeves, fit looser through the torso and have a higher neckline. All of those features make for a much happier experience for me and I am wont to purchase men’s tees in bulk. Judge me, fellow shoppers. I dare you.


I’m sure all my fellow, shall we say, “well-endowed,” girls out there have suffered from “Loosen Up My Buttons” syndrome. While Nicole Scherzinger and her fellow Pussycat Dolls make it look hot, we all know what it’s like to glance down and realize all our buttons are firmly secured except the one smack dab over our “assets,” which is the button we most need buttoned. With a men’s button-down, however, this is never a problem. Men’s shirts have far more room in the chest and have a boxier shape in general. Though you may not always be looking for such a loose silhouette, they’re a great option for those of us who always seem to be coming undone.


This may not be as obvious as some other menswear options, but men’s jackets, blazers and sweatshirts are oftentimes way cooler than their female counterparts. I love a men’s military-style jacket paired with something ultra-feminine, like a sequined skirt and pastel ballet flats. Or a men’s leather jacket with skinny jeans and a silk tank — wearing men’s clothes is all about finding the balance between feminine and masculine. If you opt for a blazer, be sure it still fits well through the shoulders. A long boyfriend-style blazer can look great paired with a form-fitting mini skirt, but if it’s too big, you’ll just look like you’re doing the walk of shame.

Dear Avery,
I recently reconnected with an old flame and we set up a date for next week. The problem is, he hasn’t seen me since high school and that was seven years and 30 pounds ago. I don’t have time to actually slim down, so what can I wear that will hide the weight gain and still make me look smokin’ hot?

Before you begin to worry about your outfit, you need to get more comfortable with your newly-bodacious bod. Sure, you may not be 17 anymore and have the body of a Disney Channel star, but a few extra pounds might work on you. Even if it doesn’t, you can’t go into this date trying to hide something or feeling uncomfortable with your appearance. Flaunt what you’ve got, and if he is disappointed you don’t still look like your teenage self, maybe you should be questioning his creepy taste in women.

I do, however, understand that you want to look trim and fit in all the right places and the right outfit can do just that. First of all, you need to pay attention to color and print. Small florals and wide horizontal stripes practically scream “Stare at my muffin top!” And don’t even reach for your white jeans — they’re off-limits for this occasion. White only enhances excess bulk, especially if in a form-fitting silhouette like jeans. I’m guessing you’re not going for the beached whale look here, so put those pants back where you found them.

Instead, opt for black jeans. You may not usually wear black jeans in the summertime, but for this occasion, I think they’ll work. If you feel too dreary, choose a pair of black skinnies that hit right at or a little above the ankle — slim cropped jeans are a great date night option for summertime. And you know what else is great for a summer date night? Wedges. Extra points for strappy metallic wedges. 

Whether you carry your weight in your hips or your stomach, a loose tank will cover all of that. A silk top in a jewel tone or metallic that hits a little below the hips looks best on ladies with a bit of a food baby. If you have little in the middle but you got much back (in the wise words of Sir Mix-A-Lot), a top that meets the waistband of your jeans will accentuate your small mid-section.

Most importantly, be sure to call attention to what you do love about yourself. If you have luscious locks, spend extra time on your hair. If your eyes are more alluring than the Mona Lisa’s, play up your peepers with dramatic make-up. Great gams? Opt for shorts or a skirt instead of pants to show off those toned legs. And if you have a great rack…well, you know what to do. Best of luck!

Photo courtesy of Flickr / CHRISTOPHER MACSURAK

TAGGED: body type, boyfriends, boys, mens style, menswear, weight gain

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