Women's Clothing for Men

Congratulations on having the confidence to be yourself! I'm proud of you and I know you'll look fantastic.

For a daytime wardrobe, it would help to know a bit more about your personal style-do you prefer a more tailored look, a hip look, or a more feminine look? We can focus more on specific looks once I have a better feel for what your preferences are.

That said, to build a smart daytime wardrobe, start with a three-piece suit (jacket, skirt, and pants) in a neutral color that flatters. Black is a great bet because it's so versatile--everyone needs black pants and a great black skirt. These will serve as the building blocks, and you can mix and match the pieces as you like. When you get them dry-cleaned, though, make sure all three pieces go so that they wear evenly.

Next, add a couple of shirts--tailored silk blouses are usually a good option, but if you have a lot of chest hair or want to conceal your Adam's apple, go for a mock turtleneck or full turtleneck in a lightweight fabric (Banana Republic has some beautiful silk ones with gathering at the neck that would further camouflage a prominent Adam's Apple--and they're on sale right now, too).

I would also recommend another skirt in a different color and style--maybe a longer one, that also coordinates with the jacket, and another pair of pants that does the same thing. A long cardigan sweater or duster will also expand your options.

For shoes, choose one pair of well-made pumps that matches or coordinates with your suit. Are you used to wearing heels? If not, make sure you choose a pair with a very solid heel. One of my favorite looks right now is a very wide heel in the back that is narrow when viewed from the side. It gives you sort of the look of a stiletto from the side while providing the stability of a wide heel. A pair of lower-heeled shoes will complete the essentials of your wardrobe. I would recommend you stay away from flats, though--your look will be more feminine in even a small heel.

As for boots, right now is jackpot time because the stores are clearing them out. There are a lot of different things in fashion, but the most popular toes are either very pointed or squared off. You have a lot of options with heels and with heights as well. The heights I've seen most often are boots that hit at the bottom of the calf, and those that go up to your knee. Try on a couple of different styles and see which ones flatter your legs the most.

As for which outfit is better for your night out with friends, I think it boils down to which you feel more comfortable in, James. Both looks sound very elegant. A pair of heels will work well with the pants, and some strappy heels or some knee-high boots would probably look good with the dress. The most important thing is to match the "visual weight" of the dress and the shoes--if the straps are substantial, the boots will look good. If the straps are more delicate, I would recommend the strappy heels (some high-heeled Mary Janes might be cute!)

I hope this helps; please feel free to write back and tell me more about your personal style, and we can work from there. Good luck to you--I know you're going to look great!!!