ASK HER: Do I Need to Step up My Style Game (for a Well-Dressed Woman)?



You ask, she answers. Have a burning question about dating, sex or relationships? Drop a line to

The girl I’m dating always looks super stylish, and I’m starting to feel self-conscious. Clothes were never that important to me TBH, but do women care about what we’re wearing as much as they do about their own wardrobes?

— Brent, 28, Newton, MA

photo-1467664631004-58beab1ece0dThe short answer: no. The majority of women don’t care quite as much about what you’re wearing as we do about what we’re wearing. But of course, it’s a little more complicated than that (are you really that surprised?)

I don’t know what your closet looks like, but that’s actually not what I’m concerned about. The fact that you’re starting to feel self-conscious—that’s what we need to address here. Is she making subtle suggestions for what you should wear or buying you clothes all of a sudden? Either could be a hint that yes, it does bother her that you’re not putting a lot of effort into your look. But even if she’s dropping no clues, you still want to feel good about yourself when you’re out with her, right? So if your instinct says that you might need to step up your style game, then you’re probably right.

Which brings me to a very important point. In no way does this mean you have to go blow your whole paycheck on designer threads. The kind of girl that expects or demands you to do that—well, in my humble opinion—is shallow AF. On the other hand, it’s ultra simple for guys to make little tweaks to their everyday ensembles that make a big difference.

What it all comes down to is knowing which pieces you can skimp on and which ones to splurge on. You can wear a $10 H&M v-neck T-shirt and no one will know it’s not James Perse. Similarly, few people will be able to tell those gray twill shorts came from Zara Men, not Jack Spade. But when it comes to items like footwear (and, while we’re on the subject, outerwear), do not, I repeat do not cut corners. Shoes matter. Women notice them right away. They say something about you. I can’t quite put my finger on it—but it has something to do with integrity. Think about it this way: Your feet take you from A to B to C every damn day—so treat them with some respect and dress them in something nice, whether that’s a classic pair of Sperry Top-Siders or Cole Haan leather loafers. Bonus: In a walking city like Boston with totally unpredictable weather, quality shoes will last you a hell of a lot longer than a cheap pair, meaning you actually save money in the long run because you’re not constantly replacing them.

photo-1462212018902-1ca14eec1bb2When it comes to men’s style, it’s all about the little things. A well-made watch by a reputable brand is a smart investment. It says you value time. You have things to do. You’re on a schedule. You’re a goddamn adult. Men’s accessories are a subject everyone seems divided on depending on personal preferences, but watches? Basically every woman will agree it looks damn good on your wrist. Find one that reflects your personal tastes, whether that means a sleek stainless steel piece or a leather strap with a larger face.

Lastly, but certainly not least: be mindful of fit. It’s far more important that your clothes hang well on your body than whether they’re made by a high-end brand. I used to work for a luxury British men’s designer in Boston, and I can’t tell you how many guys came in attempting to buy shirts and jeans that were a size too big for them. On the whole, men seem to have an intense fear of wearing clothes that are too tight. So let’s clear a few things up. A well-fitting shirt should: have shoulder seams that rest right around the edge of your shoulders, fit snug yet comfortably enough around the chest, under the armpits, and across the upper back that you still have a full range of motion, have a hem length that allows you to wear it tucked or untucked, and taper in from the wider part of your chest to the narrow part of your waist, creating a clean line so there’s no excess, billowing fabric when tucked in. Your jeans/pants should feel comfortably snug around your waist, and while a well-made belt is always a nice touch, it should never be necessary to keep them up. There should be a slight break in the front where the hem of your pants meet your shoes, and the back of the leg should just reach the top of your shoe’s sole.

Don’t know where to start shopping? Ball and Buck over on Newbury St. stocks the kind of apparel that both won’t go out of style and will hold up over a lot of wears and washes—and every piece is made in the U.S.A. Check out Bonobos on Dartmouth St. in Back Bay—I’m a big fan of their summer-weight casual button-downs, washed chino shorts and pants. All of the brand’s bottoms are made with their signature curved waistband, which ensures a better fit, and since they come in four different cuts, you’re bound to find one that’s perfectly suited to your body type. If you feel like your wardrobe is looking a little yawn-worthy, SAULT over in the South End packs classic pieces with a playful twist that will punch things up. And the Nordstrom Rack in Copley Square is hit or miss, but overall tends to have great deals on shirts and denim with tried-and-true brands like VINCE, Marc Jacobs, Ben Sherman and Barbour, so you can get more bang for your buck. Also, their shoe department tends to be a goldmine for boat shoes, derby/oxford dress shoes and driver shoes.

To recap: If you feel like you’re not measuring up in the style department, that could become an issue considering the fact that your confidence is often the most attractive factor to any woman. But remember—it doesn’t take a ton of effort—or money—to look put-together.

Rebecca Strong

Rebecca Strong

Born and raised in CT and having lived in Boston for a decade now, it's safe to say Rebecca is a die-hard New Englander. (She tried moving to L.A. once...and was back on the East Coast in four and a half months). Since graduating from Emerson College, she's contributed to numerous local and national publications—which have included The Huffington Post, BostInno, Elite Daily, U.S. News & World Report, and Stuff Magazine—covering a range of topics from technology and travel to style and beauty. Now she's most interested in helping the men in Boston (and beyond) boost their sex, dating and relationship IQ. Meanwhile, she's currently pursuing her master's at The Boston Conservatory. When she's not writing, Rebecca can be found in a kickboxing class, drinking a generous glass (or three) of wine, watching a Bs game...or patiently waiting for hockey season to return.

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