Doubtless I’m taking this “styling game” too seriously, but the idea that there is always a “right” way to style is annoying and potentially stifling to your creative impulses. (If you don’t want to click over, it’s a game in which you choose the right piece from multiple choices to complement an outfit.)

Would it surprise you to know that I got the “wrong” answer about half the time? It shouldn’t. You shouldn’t think there is one solution to every look. When I got an answer wrong, it was because I preferred my choice over the “correct” option. My taste is different from that of whoever designed the game–not wrong.

How do you develop your own taste and an eye for what works for you? Experiment. Try different combinations at home. Build up your confidence. Wear them to work, on errands, out to dinner. You’re not a celebrity, I’m guessing, so if you do miscalculate a little, it’s not going to be splashed on TMZ. (On the other hand, it can be helpful to pay attention to reactions—but you have to sift out the sincere from the insincer,e, the knowledgeable from the clueless.)

And always keep some perspective: They’re just clothes, after all!

A potential styling client recently asked me, “Could you describe your philosophy?” And it occurred to me that it might be a good idea to post it here.

It feels odd for me to be a stylist and a fashion writer sometimes, because I am not a huge fan of our consumerist society, and in many ways fashion has been taken over by that mindset. I sometimes worry that potential clients expect me to waltz in like Rachel Zoe with big sunglasses and a vintage Halston dress, tossing out mots like “I DIE” every ten seconds while a small army of assistants do my bidding. I do wear big sunglasses, but otherwise, my mode is much more down to earth. After all, I’m not dressing celebrities. I’m dressing real women who have busy lives and are lacking an endless supply disposable income to devote to turning their wardrobe around.

This is not me.

My approach to styling is to identify the client’s lifestyle, preferences, coloring/body shape, and budget and to let that drive my recommendations. I am all about style and not necessarily “fashion”; I think personal style is more important than following trends and that less can be more. I believe in investing in certain pieces where appropriate and i hate cheap-looking clothes, but I do also occasionally find stuff at H&M, Forever 21, etc. I think it’s important to have a plan and a vision before you start shopping. I don’t care about celebrities, brand names, etc. For me it is all about knowing what works for you and picking and choosing accordingly. For most of my clients, rehauling their wardrobe might mean tracking down 6 to 10 key pieces.

I’m not a bargain-hunter. I believe in spending a lot of money on a dress or shoes if you adore them and know you will wear them for years. I think it’s worth it to pay more for quality in items that are going to get a lot of use. I don’t think you should let anyone make you feel guilty about spending money (wisely of course) on clothes and accessories. However, I do keep clients’ budgets in mind, and I like shopping at places like H&M and Zara for cute tops, accessories, and super-trendy items to round out your closet and keep it updated.

Most of all, I think it’s important to have a plan and a vision before you ever set foot in a store.  For me it is all about knowing what works for you and picking and choosing accordingly. You wouldn’t go into a grocery store, browse the aisles, pick out what appeals to you at that moment and then go home and expect to make a delicious meal out of your purchases. You have a list, you have some meals in mind. Planning your wardrobe is the same. These days, there probably isn’t one store where you can find everything. Sizes are all over the place. Therefore, everyone has to be their own stylist in a way, casting a critical eye at the offerings, figuring out what will work for you, and acting accordingly. It takes time and effort, introspection, research, and discipline–but it’s worth it in the end.

Here’s the clip from today’s WGN Midday Morning News of the segment I hosted featuring some fall looks from Avenue, including a new denim line. Not sure why I can’t embed it but here’s the link:

WGN News clip

Want to know about the trends this fall? I’ll be on the WGN midday news on Tuesday, August 30, talking about fall looks for plus-size women, featuring clothes and accessories from Avenue. I’m excited to tell you about them. It’ll be on some time between 11 and 11:30 AM. Wish me luck!

Check out these designs made out of the store’s garment bags.

Often I fall in love with a certain look and I wear variations of it over and over. For example, right now I have totally hopped on the striped shirt bandwagon. I just love how they combine elegance with sportswear. I have one from J. Crew (that is not the exact one, but you get the idea) and one from Target. My favorite weekend uniform these days is a striped shirt with a short black one-button cardigan I got years ago at Express, of all places. The cardi is longer than the shirt, so you get the layering action. I wear it with skinny jeans and some suede ankle boots. I am an accessories fanatic, so I usually put on a giant cocktail ring with a blue stone I got at Tula and a bracelet from Etta Kostick, a local designer here in Chicago. (I like the way the Mondrian-like structure of Etta’s design calls out the stripes in the shirt.) To be more dressy, I’ll wear the shirt under a jacket, with army-green cropped cargo pants and some Chie Mihara heels. Occasionally I like to channel Gabrielle and wear it tucked into high-waisted, wide-legged black wool pants and flats. I use a ribbon from Hermes, the one they use to tie up their famous orange boxes when you make a purchase, as a belt. Maybe I’ll add a gold chain necklace or two, or maybe not.

My point: you don’t have to reinvent the wheel. Everyone and their mother is wearing striped shirts these days. The difference is in the way you wear it.

This week I went on Chicago Public Radio’s Eight Forty-Eight to talk about the state of fashion in Chicago–including trends, whether Chicago is really a fashion capital (no, not yet), and more. You can listen to the segment here.

I was also interviewed by AOL’s StyleList about whether it’s OK to wear white after Labor Day, and if so, how? (Hint: don’t wear white linen.) My thoughts are in this article, along with tips from Charla Krupp, author of How to Never Look Fat Again.

Hi there. It’s been a while! As you’ve probably noted from my Twitter feed, most of my blogging energy these days goes toward the fashion blog at the Chicago Reader.

However, I did notice this article over at the Wall Street Journal that I wanted to share with you. It deals with a conundrum that many of my clients face as they get older:

It is likely that I will land a job as a human-resources executive with a company where most of the other executives are fit and energetic men in their 30s and early 40s. I’m a 52-year-old woman, size 16 and 5 foot 2, and I want to exude a youthful aura; I want to avoid a matronly look yet convey “approachable authority.” I tend to wear dark slacks and silk shirts (with a thin sweater over my shoulders) or dark colored pants/jacket; I wear interesting high-end jewelry and medium heels. What do you suggest, and what should I avoid?

There’s some good advice in the answer, particularly about being too “matchy-matchy” and staid. You don’t have to change over your whole look: the answer can be found in updated details and a more contemporary fit.

What’s the deal with pantyhose? Is it still a must in the office–or anywhere else?

As it’s skirt-wearing season, this questions comes up a lot–especially since hose seems to be making a little bit of a comeback, especially patterned stockings. I’m not a big fan of pantyhose, although men seem to like it (and occasionally wear it themselves, apparently). However, what men don’t understand is that women usually dress either to please themselves or to impress other women–not for men.

I really think in this day and age are unnecessary. Unless you are older and/or prefer to have more coverage on your legs, skip ‘em.  As for the office, some workplaces are more formal than others. You may be stuck with them if you work in a conservative field such as finance (in which case I suppose having to wear hose is a small price to pay for still having a job) or the law. Hose should be either sheer (no horrible suntan shades, please), black, or navy, and you should spend a bit more for quality, i.e., don’t buy the stuff in the plastic eggs at the drugstore. I hate the fact that hose are so fragile and expensive. If I worked in an office where they were part of the dress code, I would demand that the company reimburse me. After all, men don’t have to wear items of clothing that cost at least $20 a pair and last two wearings if they’re lucky.

Just got back from a quick trip to Miami. I didn’t take any pictures of what people are wearing–I mean, you can imagine, right? Lots of bikinis and cover-ups. There were some lovely boutiques but also a lot of, shall we say “flashy” clothing. We also saw a guy with a snake around his neck and another man on a moped with a parrot perched on his shoulder. (We just needed to see someone with a panther on a leash to win South Beach Bingo.) I was more impressed by the interior decor and architecture there.

The lobby of the gorgeous Delano Hotel in South Beach. I would love for my home to look like this. No, we didn’t stay there. Maybe next time!

All images copyright Heather Kenny.

Drinks at another cool hotel bar, the Shore Club. I swear we did more than have cocktails on this trip.

All images copyright Heather Kenny

Casa Casuarina, onetime home of the late designer Gianni Versace. It’s now an ultra-exclusive boutique hotel and restaurant. Versace didn’t build it (although he did undertake some major alterations)–it dates from 1930. And yes, he was tragically murdered on its steps in 1997.

All images copyright Heather Kenny.

So we don’t end on a sad note, here are some palm trees. Think warm thoughts!