There is nothing more than the Modern Gentleman loves than women.  Women are just the most wonderful creatures on the planet.

It is through the enigma of women that I have had to answer the question, "How do I look?" many many times, and The Modern Gentleman does not tell a lie.  I pay a great deal of attention to women’s fashion, so I often answer in detail. 

What follows is a brief and not at all comprehensive summary of some of the things I have had to say in response to that question over the years.


Every woman looks amazing in a halter dress. In the summer, they’re light and breezy, and in the winter they can be combined with scarves and jackets. Either way, wonderful.

But the Modern Gentleman must confess: he has never seen a flattering strapless dress. 

I can only assume this is why bridesmaids are forced to wear them. Most strapless dresses rely on the bodice opening instead of an adjustable shelf to hold up the skirt. This means that the weight hangs on the top of your breasts, much more than gravity should allow. If you’re small-breasted, you will spend all evening pulling the dress up. If you’re large-breasted, the top of the bodice will flatten you down in an odd way. A much better option is to find a great skirt and match it with a flattering strapless top.

The ugly stepsister of the strapless dress is the necklace dress.  It’s an amazing thing that every woman looks so wonderful in a halter, but no one call pull off the necklace dress — something constantly misidentified as a halter. 

This unflattering tie-up makes your breasts — if not the entire dress — hang like an albatross about your neck.

What evil looks

Had I from old and young !

Instead of the cross, the Albatross

About my neck was hung.

– Samuel Taylor Coleridge

The Rime of the Ancient Mariner


The pencil skirt is a bizarre item. Women tell me they’re comfortable to wear and quite supportive, especially in the abdominal area. But if you’re petite, they dull your shapely hips.  If you’re bigger, they make you look misshapen, as if somehow you have a gut that begins below your waist. Also, by changing your waistline you shorten the distance to your bra line, which creates the optical illusion of sagginess. A bad pencil is the skirt equivalent of mom-jeans.

What we gentlemen learned from Tom Ford in the nineties that was sometimes the most comfortable clothing is also the most flattering. The right skirt shouldn’t hide or divert anything about your body, it should celebrate it. Pencil skirts hide and divert. 

Perhaps the best way to fix this is with an oversized belt. This will give you fantastic silhouette definition and comfort. 


Men don’t want to see padded bras.  We fell for them in Junior High School, and we still love you for it, but it’s time to be yourself. I’ll tell you a thing about the Wonderbra: until 2006 it was owned by Sara Lee, the cake company known for making good-looking yet disappointing cakes. It is far sexier to show off your real shape and (I’m told) much more comfortable in the heat.  

For a casual bra, try The Fiance by The Lake & Stars.

There are also myriads of light undershirts with comfortable shelves. Going braless is one of the perks of having smaller breasts. If you can swing either of these alternatives, do. They’re both comfortable and sexy. 

If you are in the New York area and you want to get a few opinions on bras, try these two (very different) stores:


  • The Orchard Corset Center -157 Orchard St., nr. Stanton St. 212-674-0786

    This old-school shop leaves the wardrobe department of Mad Men positively salivating.  The sales staff is known for being gruff but honest.

  • Intimacy – 1252 Madison Ave., at 90th St. 212-860-8366

    This shop is much pricier, but worth it for that special-occasions bra, or to fit larger sizes.

Knickers: It doesn’t matter. We love you in all of them.

I will say this, though – when you get a new boyfriend, buy a new set of underwear to leave at his house.  These will delight him on laundry day and give him a little smile every time he runs across them in his sock drawer. 


Modern advancements in hosiery are not in panty hose, but in making regular thigh highs that do miraculous things like stay-up.  I have a poet friend who once said "I don’t understand why anyone over the age of 12 wears tights, when thigh-highs are sexier, comfier, easier to clean (none of this water-weighted-crotch-falling-into-the-tub business), and more conducive to illicit affairs."

She pointed me towards these:

They’re designed with silicon bands and do not require garters. I’ve been told that panty hose are more comfortable to wear with evening wear because they do not leave panty lines, but do keep in mind that panty hose tend to add a mom-jeansesque waistline.


Pants have to match the occasion, of course. But a good pair of jeans can work in almost any situation.

Top Shop’s Indigo Straight Martha Jeans are utilitarian and flattering, but wouldn’t you rather just save up for a pair of D&G jeans?

In general, you should be aware of a few things in jeans:

  • Pockets: should accent your hips and rear.  If they are too tiny they will make your bottom look too large.
  • Waist: should sit lower than where you would wear a skirt or even dress pants.  The belt should sit right atop your rear.
  • Color: My, this changes every year.  Try and avoid overly trendy shades and washes. A classic color fades nicely on its own.

Also, any jeans that you feel you need to retire are perfectly ready to become a prized pair of cut-offs. Women, unlike men, always look great in cut-offs.


We’re conflicted about shoes. On the one hand, heels make your legs look even sexier than they already are. On the other, nothing ruins a beautiful look like a pained expression. Compromise between comfort and style is key here.

In doing research for this shoe sections The Modern Gentleman dide a very non-scientific survey of the hardest working women in heels: cocktail waitresses.  They all agree on the magic of cork-wedge heels

Although The Modern Gentleman has no first hand experience in cork wedge heels, I suspect that these ones by Marc Jacobs would be a fantastic three-season purchase. 

Although many of them are in open-toed styles, the thick soles will insulate your beautiful feet from cold floors and sidewalks in the chilly months.

A Final Note

All women look amazing in a man’s dress shirt. If you wear mine out to grab the Sunday paper, maybe with only one button done — we’re not going to be doing much reading that afternoon.

Images courtesy of the Fashion Spot forums.