Monthly Archives: August 2010

The Gentleman: Suiting Up

To Pleat or Not to Pleat

This week, the Gentleman had hoped to show everyone some photos from his End of Summer/House Warming party. After having the party pushed back a week, I had another disappointment on Saturday night: although the party was great, no one wore anything interesting enough to blog about! Do not fear, I have several exciting events that I will be attending in the coming months where there are sure to be stylish people, including a black tie dinner, that will be blogged about.

I was looking through my closet a couple of days ago and realized that I was desperately short on trousers. The only pants I own that I could wear during autumn and winter is a single pair of khakis and two pairs of jeans (one nice, the other less so). Of course, I own several pairs of suit trousers, but I try to avoid wearing those without their accompanying jackets in the hopes of preserving the life of the suit. In the coming weeks, I plan to pick up a couple of wool dress trousers to better complete my wardrobe.

Aside from material, the most obvious and important style considerations for trousers are pleats and cuffs. Of the two, pleats have become a bit misunderstood. Today, they are viewed alternately as too dressy or too frumpy. The Gentleman would like to clear up a few misconceptions about pleats and explain how they have their particular purpose in some gentlemens’ wardrobes.

Pleats are folds in the fabric of a pair of trousers that begin at the waist and vanish about midway down the thigh. Some men’s dress pants have a single row of pleats, others feature two rows of pleats (double-pleated), while still others have no pleats at all (flat front trousers). Today, flat front trousers are more “fashionable,” however, both pleated and flat front trousers are classic and each have their defenders. Because The Gentleman is more interested in what makes a timeless and practical wardrobe, he will not write off pleats just because they’re not trendy at the moment. Instead, we should examine the purpose of pleats and think about who they suit best.

Here is an example of each type, a pleated trouser and a flat front trouser:

Pleated Trouser: Brooks Brothers

Flat Front Trousers: Ralph Lauren

The first thing you should notice when comparing the two types of trousers is that pleated pants are worn a bit higher. This is the key to understanding the pleat. As may be intuitive, the waistband of a pair of pleated trousers is meant to be worn at a man’s waist. There seems, however, to be a misconception about where the waist is; it is about an inch below a man’s belly button, varying depending on the man’s height. Traditionally, men wore their trousers at their waist, but today many men wear their trousers sitting on their hips. This makes a big difference when it comes to whether you want to wear flat front or pleated trousers.

On most bodies, the waist is the narrowest part of your body and your hips the widest. If you wear your trousers at the waist, you’ll need them to flare out slightly at your hips and then taper down through the leg. Pleats perform this feat admirably as the folds open up slightly through the hips and then disappear through the leg. However, if you are wearing your pleated trousers at the hips as many men do today, you’ll be stuck with baggy folds of fabric below the widest part of your body, exactly where you don’t want it. I believe that men improperly wearing pleated trousers on their hips has led to the impression that pleats are baggy and frumpy, which has decreased their popularity of late.

If we understand that pleated trousers are meant to be worn at the waist and flat front trousers at the waist or the hips, the question becomes: where do you want to wear your trousers and which of the two styles of pants is the most flattering for your body type?

A man with a bit more weight in his middle will benefit the most from wearing pleated trousers at his waist. This is because his belly probably sticks out a bit more at his waist and the pants will sit there nicely and fall directly in an even drape to his shoes. The pleats will provide enough room and comfort through the hips without looking gigantic and baggy the way flat front trousers would. He will also avoid the problem of having his belly protrude over the waistband of his pants the way it would if they are worn on his hips, an increasing problem with today’s ubiquitous flat front pants.

A slimmer man need not fear wearing pleats either, but may benefit more from the cleaner, slimmer look of flat front pants. As they sit on the hips, the trousers will complement his slimmer physique more than pleated pants do. The only type of man who needs to avoid pleats are very tall, thin men. Sitting a pair of pleated trousers high up on a tall man’s waist extends his legs in a way that often makes him look silly.

When we understand the distinction between wearing trousers at the waist and at the hips, it becomes obvious why both pleated and flat front trousers are classic styles. They do different things for different men.

I’m certainly not a heavy guy, but I’m not as thin as I was in college. I’ve traditionally worn flat front trousers and probably will continue to, but when I try on dress pants in the next few weeks, I’ll take a few pairs of pleated trousers into the dressing room and give them a chance to make their case.

Next time: The Gentleman spends two weeks trying out two new pairs of fall dress shoes…



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Labor Day Linen

We know many offices reinstate formal work attire post-Labor Day, which is only one week from today! So in honor of summer casual dress codes, we have decided to pursue a week of casual outfit posts. We want to end summer 2010 with the sweet memory of relaxed and comfortable style!

This outfit is by and large the most comfortable one I own. I know I’ve sung the praises of this easy-to-wear combination before, but this blows it out of the water. The top is a very light cotton – it’s so much softer than my other casual tees. I am now on a quest to replace all of my “regular” t-shirts with ones made from whatever kind of special cotton this is.

Whether I’m working or weekending, I’m always looking for ways to keep my hair out of my face. I love wearing it down, but when it won’t stay in place it drives me up the wazoo. I’m sure that pet peeve stems from a childhood filled with tight pony tails, always-trimmed bangs and a mother who frequently insisted: “keep that hair out of your face!” Haha, thanks Mom. So this headband was the perfect addition to the ensemble because I wanted to wear my hair down without it blowing into my eyes… and it adds a touch of hippie flair.

Please excuse my poorly executed pedicure. Ahem… onto my point: As much as I love how these shoes look, they are completely impractical. I would never wear them out to anything that involved a substantial amount of walking (which pretty much encompasses everything in this city), but in the back of my mind I’ve always thought they’d be perfect for a day spent lounging at the pool. Due to my lack of pool-going, they’re often held hostage in my closet. Every once in a while I do manage to take them for a stroll, but mainly because I support the No Shoe Left Behind Act. No pair of shoes should be abandoned in my closet, not even the most impractical, complexly tied, tassle-swinging ones.

Lindsay’s Look:

Top: Urban Outfitters, $54

Headband: Gift from Mom

Necklace: Gift

Linen Pants: Free People, $20

Shoes: c/o Nicole Miller


Filed under Casual Style, Lindsay's Looks

Style Inspiration: Katharine Hepburn

One can’t help but think of Katharine Hepburn when looking at this fall’s tailored menswear trend. The trousers, the blazers, the low-heeled shoes – she started it all! Back in the 30s and 40s when women were still expected to wear dresses and heels, Hepburn was forcefully refusing to wear anything but pants. She even famously walked around set once in her underwear when her slacks had been stolen in the crew’s attempt to force her into a dress. There was no making this woman conform to the times.

Many of her male Hollywood bosses weren’t so impressed with her defiance, but women all over America were inspired by Hepburn’s gall and started wearing trousers themselves. Although there is some debate on whether we really can attribute the revolution of women’s dressing to Hepburn’s championing of the style, her influence is undeniable. As a major movie star, her fashion choices were news, but her wonderful acting and colorful personality were also part of what made her style appealing. Her pants came to symbolize independence for women not only because they provided freedom of movement, but Hepburn herself was an inspiration as a talented, successful, outspoken woman known for being able to hold her own with the men of her industry, both executives and actors.

Personally, I’ve always admired Hepburn for her talents and her lifelong commitment to a simple and chic style. My research only led me to feel even more like a kindred spirit as I learned that she was also a fellow tall woman, a women’s college graduate and her family heritage lies in the British Isles. It’s no wonder I always found myself drawn to her style and persona! At five feet and seven inches, she was the tallest leading lady of her time, and her years at Bryn Mawr college were formative in the development of her acting skills and outspoken personality. Hepburn was also known for her athleticism (did her own stunts!), so maybe that’s where our similarities end. Training for road races is in my future, though!

To achieve the status of style icon means you must be more than a pretty face, and Hepburn was clearly so much more. Not only was she strikingly beautiful, she was passionate, trail blazing, intelligent and immensely talented. She remains the only person to have received four Best Actor/Actress Oscars, and she was declared by the American Film Institute to be the greatest female star of American cinema. She left her mark on American style, film and women’s liberation – no small task. So when I choose which pieces to add to my wardrobe this fall, Katharine Hepburn won’t be far from my mind as I pick through high-waisted trousers, button down blouses with the perfect collars for casual popping (as she so effortlessly does below) and kitten heels to give me just a little lift, the whole time striving to look just as classic as the lovely Kate.

All photos courtesy of Corbis Images

Emulate the Great Kate:

Find the perfect button down:

Modcloth: Dapper Ann Blouse, $35

Banana Republic: Monogram silk tuxedo shirt, $60

… and then match it with a fabulous pair of trousers:

Forever21: Business Pant, $23

Victoria’s Secret: Belted Trouser Pant, $40

Victoria’s Secret: High-waist Pant, $78

TopShop: 70s Cord Flare by Boutique, $160

Theory: Alleen Pants, $255


Filed under Side Notes

What’s Your Cubicle Chic?

Sara Hennessey, Freelancer at

What you choose to put on in the morning as you get ready for the work day is what we’re all about. At Cubicle Chic, we focus on assembling stylish outfits for a corporate office environment, but not everyone who goes to work sits down at a cubicle like we do. Many people don’t even enter an office building or have a desk to go to.

In an effort to showcase the many different styles of dressing in the working world, from corporate to creative, we have put together a new segment called “What’s Your Cubicle Chic.” We plan to bring you stylish men and women from all different industries in New York City with the hope of one day including readers’ inspiring style from all over the country (dare we say world?).

Our first brave contender is Miss Sara Hennessey, freelancer and CMS extraordinaire at Hearst’s We traveled to Sara’s adorably decorated apartment in Brooklyn for her shoot, and it became apparent quite quickly that she’s a natural. Talking about her work experience made Cubicle Chic a little jealous… we wish we could work from our couches!

“Freelancer on Her Day at the Office”

“Freelancer Working From Home”

In an effort to capture Sara’s full philosophy on style, Cubicle Chic asked her a few questions. All you aspiring freelancers out there, listen up!

What defines your personal style?
I like to think of my style as a ‘tailored vintage’ look. I’m a really big fan of very classic looks (eg. the khaki trench coat, black pencil skirt, wayfarers), and I always like to look polished (I’m That Girl that tends towards matchy-matchy and can’t wear silver and gold together), but I love wearing vintage. The clothing is so beautifully-detailed, and I find that vintage styles suit my figure best. My favorite Brooklyn vintage clothing store sells these amazing re-worked vintage fashions, and I never walk out of there without three new dresses. Oh yes, and dresses are my “thing,” I’ve officially stopped buying pants. 😉

What do you love about the looks that you wore for the “What’s Your Cubicle Chic” shoot?
I think it’s a pretty good reflection of my own personal style, which is to take classic pieces (the black blazer and the white shirtdress) and put my own spin on them. For example, the jacket is something my mother bought me for like $5 years ago, and it’s too large to wear as a business-y jacket-pants combo. However, it works perfectly as an oversized blazer that I can pair with items like the shirtdress, which, on it’s own, would be too sheer and short for the office, but looks chic when paired with the jacket.

Do you have any signature or favorite go-to items you couldn’t live without?
Absolutely! I could not bear to be with out my favorite nude pumps. They go with everything, and they add about four inches my 5’3 frame, which I love. I also have two rings that I would be lost without. One is from my grandfather, and the other is from my father. I always think of those two amazing men when I wear them, and they give me some happy, positive, confident vibes that I think are the the best way to top off any outfit!

Where do you find your style inspiration?
I am a magazine fiend. Honestly, it’s ridiculous how many magazines I subscribe to (12 is not too many, right?). So mostly, my inspiration comes from the pages of BAZAAR, Vogue, Marie Claire, New York, etc. Beyond that, I adore reading fashion blogs and sites. I’m always intrigued by interesting ways to put together clothing, mix fabrics and prints, and just interpret what’s on the runway and en vogue into something totally unique. Some of my favorite bloggers are What I Wore, My Style Pill, The Clothes Horse, and, of course, The Sartorialist.

Have you ever made some fashion faux-pas that you now regret?
More than I can count, undoubtedly! My mother dressed me until I was in middle school and I realized that that just needed to stop; but, the years prior to that were filled with huge hairbows, massive knit sweaters with huge jewels and puppies on them, and more pink flounces that should ever happen to a person. Then, when I was in the fourth grade, I had this pair purple velour overalls that I literally wore until they just fell apart from overuse. They were hideous, but I thought they were fabulous. And then, my freshman year in college was when gaucho pants were very en vogue, and don’t worry, I had three different pairs. They looked horrendous on me, but I did not let that stop me.

What’s the best part of living, working and integrating your style into your life in NYC?
I adore everything about New York; from the dirty subway rats to the towering skyline. I love it all, and I count my blessings every single day that I live in such an amazing city. One of my favorite things about it is that it’s filled with so many different people, with so many different styles and attitudes. New York is one place where taking a fashion risk is welcomed and respected, and I have definitely felt that rub off on my sartorial taste. For example, I went back home for the holidays last year, and I wore something I wouldn’t have thought was bold or flashy (skinny black jeans, a black leather jacket, nude heels) when hanging out with my friends, and they all said I looked “so New York,” which… well, I’m still not sure if that was a compliment, but I certainly took it as such.

What’s the most difficult part? 😉
Feeling like I always have to look great! As much as I love getting dressed for the day, there are times when I miss rolling out of bed and schlepping around town in sweatpants and some ratty old college tee. Maybe this is a reflection of my own insecurities, but I would never think of wearing sweatpants or flipflops outside anymore.

As a freelancer, do you feel like you get to express your style in your “home” attire and your “office” attire?
Definitely! I don’t buy clothing that I am not proud to wear as a reflection of who I am. The only difference between the “home” and “office” looks is (hopefully!) that my “office” attire is more polished than my “home” attire. For example, usually something I would wear at home is also something I would also wear to the office, but with the addition of heels and earrings. I definitely put more thought and effort into an outfit I would wear into the office, just because, clearly, I want to be taken seriously as someone who works in the fashion/beauty industry.

Any style tips for aspiring beauty “dot com”  freelancers?
My mentality, and this is may not be not true for everyone, is that freelancers don’t have the same leeway that those on-staff have to go for a relaxed look. When I am meeting with my boss, I try and always look polished, professional, and chic, regardless of whether I’ll be in the office for 30 minutes or all day long. This is perhaps the one in-person impression I’m going to give my team members for a week or two, and I want to make sure I’m representing myself as best I can. You may not be able to judge a book by it’s cover, but a well-dressed cover certainly makes for a far better impression than an ill-dressed one.

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Stolen Says: Central Park’s Sheep Meadow

Glittering skyscrapers, glamorous people, fast-paced business and even faster-paced nightlife swirling by in a flash of color and lights – this is probably the most well-known and fantasized image of New York City. As much as I love the bustle of the big city with the laughter, dancing and social connections that can be made in a few hours out on the town, the calmer, more relaxing areas of New York also absolutely deserve to be appreciated.

Summertime is a season of terrace brunches and weekend trips to the beach, and it is also a time for peaceful gatherings in one of my favorite places in the city: Sheep Meadow in Central Park. Just like the rest of Manhattan, Central Park is somehow sprawling and endless despite its physical boundaries. Within its four square miles, it contains several bodies of water, numerous baseball fields, fountains, a carousel, a boathouse, and many, many patches of grass upon which New Yorkers and tourists alike congregate to spend a sunny Saturday afternoon. Sheep Meadow is arguably the most popular “patch” of grass to be found.

Located on the west side of the park, between, approximately 63rd and 68th Streets, Sheep Meadow is my favorite spot for picnics and game days, some dry and others accompanied by sangria. (Actually, most of my picnics with friends are accompanied by sangria, but that’s not the only reason we have so much fun at Sheep Meadow!)

We kicked off this summer on Memorial Day with a small gathering that included a few games and a few drinks. The weather was perfect – hot, but with a light breeze. We chose a spot near the edge of the meadow so we could opt to move into the shade of the trees if we felt our tans were becoming too lobster-like, and that afternoon was quite possibly one of the best so far this summer. The city sounds of taxis honking, construction crews drilling, buses unloading passengers and people yelling into their cell phones all fade away as you lay on the grass and gaze up at the blue sky. You can almost forget that you are lounging in the middle of one of the busiest cities in the world!

The only afternoon at the park that could possibly trump that relaxing Memorial Day is the yearly event put together by my dear friend (who is, if this is possible, more of a social butterfly than I am) in Sheep Meadow that is of truly epic proportions. This, as we have come to call it, is the Summer Social Extravaganza. He invites all of the fabulous people he knows (which is quite a few), and then all of those people invite all of the fabulous people they know. As you can imagine, it becomes one huge, fantastic mish-mash of friends-of-friends meeting friends and making connections that would otherwise never have happened. It is truly one of the most beautiful events that could occur on such a gorgeous, sun-filled summer day.

So the next time you’re in New York during the fairer seasons, you must make a trip to Central Park and spend at least two hours lazing about on your blankets spread on the green, green grass, watching the world go by.  You’ll see lovers sharing their first kiss, wizened golden retrievers shuffling after soccer balls, friends tossing a frisbee and a fair amount of beautifully sun-kissed skin. (Occasionally there are a few who are not so beautifully sun-kissed – but we give them credit for trying.) And for those of you who live in New York – summer’s almost over! Get to Sheep Meadow and soak up the sun while you still can.

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Cobble Hill Neutrals

I love, love, love getting sartorially prepared for fall. Nothing makes me happier than stepping outside on one of autumn’s first few semi-chilly mornings, knowing that it’s O.K. to wear leather boots, close-toed shoes, long sleeves and turtle necks. Just writing about it makes me impatient! Is this a sentiment that the style world shares? I know that a handful of blogs I follow have mentioned the same.

I can’t get enough of this top. I’ve remixed it about five times for the blog because it’s so comfortable and goes. with. everything. Love pieces like that! The fabric of this skirt is on the heavier side, so I would normally save it for cooler weather, but I just couldn’t help myself. It’s so comfy, and it has pockets! A pencil skirt with pockets… is paradise.

I also think I should have saved these kicks for September, but what the heck? I got them on sale at Nine West a couple months ago and couldn’t resist bringing them out for a stroll around Cobble Hill (and even earlier this year, around Midtown East. Come to think of it, this outfit is pretty darn similar to the one I wore in those photos. I suppose I have a penchant for sleeveless tops, pointy pumps and pencil skirts ;)). In a strange way, they reflect fall 2010’s “innerwear as outwear” trend because of the sexy black lace.

Who else can’t wait for fall?

Lindsay’s Look:

Top: Calvin Klein, a gift from Mom

Bracelet: H&M, $6

Skirt: Banana Republic, $50 (on sale)

Shoes: Nine West, $25

Necklace: H&M, $8


Filed under Lindsay's Looks

The Gentleman: Style Sins

The Square Toed Shoe

This week, The Gentleman was supposed to give you a peek into his end-of-summer party, however, real life intervened and the party had to be pushed back. Instead, I look forward to sharing New Orleans’ end-of-summer styles with you next week.

Today, I bring you the eagerly awaited second installment in my recurring “Style Sins” column. Let’s dive right in to discuss a particular pet peeve of mine, the Square Toed Shoe. Appropriate shoes are so essential to style that I devoted my very first Gentleman column to them. It seems that hordes of men ruin otherwise excellent outfits with poorly chosen footwear. I suspect that a lot of this has to do with skimping on shoe purchases. Men seem at ease with shelling out a decent amount of money for a suit or a shirt, but then are aghast at having to approach $100 or more for a pair of shoes when it is quite likely that they will wear their dress shoes far more often than any other part of their business wardrobe. It’s paradoxical why men won’t invest in higher quality footwear.

Another possible reason for so many ugly shoes pounding the pavement of major cities is a simple lack of understanding about what makes a shoe aesthetically pleasing. The easiest way to avoid wearing a bad pair of shoes is to ban the horrid Square Toed Shoe from your closet entirely. Below is a perfect example of an ugly Square Toed Shoe. It’s the “Run For Cover” by Kenneth Cole, which is an appropriate name considering that a Gentleman should run for cover if he ever encounters this shoe at a department store.

Photo Credit: Kenneth Cole

Unlike a lot of other advice I give on Cubicle Chic, I can’t exactly say why I think Square Toed Shoes look bad. They just do. Maybe it’s the fact that the human foot is naturally rounded and a Square Toed Shoe gives it an artificial angularity. Whatever it is about them, I think they instantly ruin any outfit.

Square Toed Shoes seem to be even more of a menace when men wear loafers. Nearly every loafer I see young gentlemen my age wearing are of the square toed variety. It does NOT suddenly become acceptable to throw style to the wind when you dress down and wear a loafer.

Photo Credit: Kenneth Cole

I save the in-depth discussion of loafers for a later post because they are the ideal shoe to wear in autumn, but for the moment, a horribly angular loafer by Kenneth Cole, the “Ring n Run,” is pictured above. Why is it that all of their bad shoes use the word “run” in the title? To show that I don’t hate exclusively (though frequently) on Kenneth Cole, below is an equally dreadful Square Toed Shoe from Johnston & Murphy. I’ve praised this company before for selling generally high quality shoes, but this shoe, their “Dobson Moc Toe,” is as ugly as both of the previous shoes.

Photo Credit: Johnston & Murphy

The alternative to buying a Square Toed Shoe is to buy a traditional, rounded dress shoe. Johnston & Murphy’s “Melton,” which I wrote about in my very first post, is an excellent example of a classic round “cap toe.” A classically designed shoe like this is not more expensive than the ugly ones discussed above.

Photo Credit: Johnston & Murphy

I’d love to hear more about your thoughts on this “Style Sin.” Are Square Toed Shoes just a personal pet peeve of mine or are they a serious style sin? Feel free to sound off in the comments!

Next time, the Gentleman will be sharing his end-of-summer house warming party and the styles that his guests wear…


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