Barely a year after local designer Robert Berry opened his Cow Hollow boutique, he’s a bona fide hit with the society set. And no wonder. He creates elegantly wearable clothes with San Francisco’s finicky weather—and real women’s bodies—in mind. Even better, if something doesn’t fit like a glove, he custom-tailors it to perfection, just like in the good old days. Working from a white Lucite table in the back of his store, Berry spends his days (and many nights) sketching designs that his muses—fashion icons Grace Kelly and Elizabeth Taylor, whose films play constantly on his iMac—would appreciate. Here, he reveals the secrets of a well-made garment and explains how to make any piece of clothing look a whole lot better.

Sometimes I show my mom a dress or top I’ve just bought, and she starts to point out all the imperfections and scold me for splurging on something so poorly made. I hate that. How can I tell if a piece is going to pass the Mom test? I always check the inside first to see if there’s a lining or if the garment is French-seamed. If not, are the exposed seams at least covered? If they’re not covered, are the edges finished with stitching? A lined garment will last longer and lie better. Most importantly, the lining feels better than exposed seams against your skin.

I notice a lot of your pieces are lined.
I like using a color that contrasts with the exterior. I also finish the inside seams with a bright silk ribbon. The edging is so thin it doesn’t show through the fabric, and it feels seamless on your body.

Now that you mention it, my vintage pieces all have linings, and they’ve held up for decades. Does the lining fabric matter?
Yes. A poly or acetate lining doesn’t let skin breathe. I line my clothes in breathable silk chiffon, which is very inexpensive, yet soft and light.

What else should I be looking for that I probably never think about?
Especially with a tailored jacket, ask a salesperson or check for yourself whether the interfacing—the hidden fabric that stiffens a garment in collars, lapels, and cuffs—has been sewed on, versus pressed on. Cheap pressed-on fusing can bubble when you perspire.

In San Francisco, you can never have too many jackets for layering. How can I size one up even before trying it on?
Look for a crisp body, which means there’s a lot going on structurally inside to help it keep its shape. For example, in the 1920s, Coco Chanel started putting a hidden gold chain inside her jackets to add weight and make them fall just right, and this is still a Chanel trademark. Also look at the way the jacket arm falls on a hanger. The arm should have a natural, slightly forward bend, because that’s the way the body is made.

What about your clothes? What are the little touches that scream quality?
Elbow darts, which create a curve in the elbow by stitching several small gathers, are rarely done today because of the added labor expense, but I do them all the time because they help sleeves fit and move better. I also like topstitching—it’s a time-consuming decorative element that demonstrates attention to detail.

I hate buttons that pop off the first time I wear something.
A keyhole buttonhole can solve that problem. It’s friendlier to the button than a regular straight buttonhole, so the button stays on longer.

And zippers that get stuck!
You’d be surprised how many people don’t test them in the store. I use the Riri brand, which is the Rolls-Royce of zippers. Louis Vuitton uses them, too. The ribbon is canvas, not poly, so it won’t rip or get stuck. It’s made in Switzerland.

So what’s your pet peeve? I see a lot of ill-fitting garments in this city.
I completely agree. I routinely pay more to get something altered than I did to buy it in the first place. People shouldn’t be so scared to get things tailored. A tailor can make anything fit better, maybe shape it just slightly under the arm or accommodate legs that are different lengths. Like the woman who just bought a dress from me for a big event—it was falling longer in front because her butt wasn’t filling out the back. Taking out just one centimeter from the back made a big difference.

Don’t stop there. What else bugs you about the way San Franciscans dress?
I’m tired of seeing women wearing a Burberry trench coat over an evening gown because they don’t own anything else. Get a really strong coat that can take you from day to evening, with an emphasis on evening, like a navy, knee-length coat in wool cashmere. Navy is softer than black, but still formal, and flattering for all complexions.

Let’s talk about black.
Women in this city need to wear more color, especially at night.

But it’s hard to make the transition to color. Black is so easy, especially at night.
You can start by playing with textures, which add depth and character. Put silk with leather, so you have matte, shiny, and fuzzy black all together. Next, find a color you’re comfortable with and wear it in solid pieces. Then think about a blocked dress with several colors. It’s not as overwhelming as a pattern, and you’ll be able to wear it again and again.

Any big color no-nos?
Don’t wear red pumps with a red dress. It’s okay not to be matchy-matchy, and it’s really not modern to match your shoes to your purse.

I’ve got a big party coming up. Shopping tips, please.
Bring the right undergarments to the store. A strapless dress will never look good with a regular bra. Bring all your shoe and accessory options, too, so you can see how the whole thing will look together before you buy.

And I suppose I’ve got to leave time for alterations.
Again, be sure to wear the right undergarments and shoes for the tailor. If you’re going to bother to get something altered, why not make it perfect?