What Chicago Guys Think About What You're Wearing

We know you trust us to keep your personal style fresh, and we love being the ones you count on. Today though, we're taking the day off, and heeding style advice from a different source: the boys. We asked 10 stylish, savvy Chicago guys, who are out and about on our city's social scene, to dish on what they love (and hate) about women's fashion.
DJs, restaurateurs, bloggers, and more share some sartorial insights from a male POV. Harem pants, highlights…the fellas aren't holding back about the looks they want to see, and the trends they hope will die a swift death. Don't worry ladies, they could do without kitten heels, too. Click through for a fresh perspective on Chicago style, and see if these gents make you view your wardrobe in a new way, or if their opinions make you love your outfits even more.
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1 of 10
Billy Dec, CEO/Founder of Rockit Ranch Productions

Do: I like when girls can rock a vintage or recycled thrift store piece mix-matched with something that is definitely not. Also, somehow integrating a piece that fits their look with something personal to their history or family. I just think it differentiates them more, to reflect their personal story, and its intriguing.

Don't: Bedazzled anything, sports gear from other cities, an attitude, and anything that makes them look like they are trying too hard to be sexy when they're beautiful just the way they are.

Reebok Pavel Datsyuk Detroit Red Wings Ladies Premier Jersey, $124.95, available at Fanatics.com.

  What should Chicago girls try more often?
Creative, passionate, local Chicago designers thriving and staying in the city because locals wear and support their gear, and promote it far and wide!

Elise Bergman Carter Dress, $385, available at Elise Bergman.


Photo: Billy Dec on Windy City Live, courtesy of Rockit Ranch
2 of 10
Brad Bennett, Style Blogger

Do: Menswear. Boyfriend jeans, worn-in button-down shirts, beat-up coats. Girls in Barbour jackets, forget about it.

Faith Connexion Cropped boyfriend-fit straight-leg jeans, $300, available at Net-A-Porter.

Don't: Silly hats. Not a day goes by that I don't see an otherwise great-looking girl ruin her whole outfit with some silly little fedora, "military" hat, newsboy cap, or some awful crocheted mess.

Halogen Leather Belt Fedora, $38, available at Nordstrom.

What should Chicago girls try more often?
I'd love to see more natural. Natural skin color, no bottle tans. Natural hair color, no highlights. Less makeup. It's refreshing to see girls embrace what they have, as opposed to trying to cover it up.


Photo: Courtesy of Brad Bennett
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3 of 10
Samm Mackin, Fashion Features Editor at Laundry Magazine

Do: One thing that Chicago girls continually do really well is incorporating vintage pieces into their wardrobe. Jealously-inducing jewelry and fabulous furs all add a certain je ne sais quoi that the ladies of Chi-town know just how to work.

L.K. Bennett Sledge Court Shoe, $298.75, available at L.K. Bennett.

Don't: I am always horrified when girls wear leggings as pants. If they would like to continue with maximum cellulite exposure then I say by all means carry on! My suggestion is to replace the legging with “the little black pant” for a similar yet more flattering effect. 

Miss Selfridge Black Ponti Legging, $32, available at Miss Selfridge.

What should Chicago girls try more often?
It would be nice to see Chicago ladies perfect the work-wear look. Too often on my morning commute I bemoan the khaki clad masses I’m forced to sit amongst. One prescription to help cure this conundrum would be the casual heel–a middle ground between the beaten down flat and the porno-chic evening stiletto, to amp up the wardrobe of Chicago’s women. 


Photo: Courtesy of Samm Mackin
4 of 10
Jason Berngard, Gilt City Director of Sales

Do: I love the festival look that Chicagoans seem to embrace: short floral dresses and boots.  I can’t wait for Lollapalooza 2012! 

Fatface Charlotte Palm Springs Dress, $72.63, available at Fatface.

Don't: I am not a huge fan of high-waisted, wide-leg trousers. I know they are considered to be stylish these days, but they aren’t doing it for me.

Mango Chino Trousers, $59.99, available at Mango.

What should Chicago girls try more often?
Summer is around the corner and I dig bright colored jeans, V-necks tees, and high heels.  Keep it simple this summer.


Photo: Courtesy of Jason Berngard
5 of 10
James Sims III, PR Account Coordinator

Do: Stunning platform heels in awesome prints and colors. I always say, “The higher the heel, the closer to God.”

Alexander McQueen Studded Leather Sandals, $2,295, available at Net-A-Porter.

Don't: Kitten heels, the worst! If you have them, get rid of them. Just wear flats.

ASOS SORT Slipper Vamp Kitten Heel Shoes, $43.63, available at ASOS.

What should Chicago girls try more often?
Girls taking the time to dress up a bit. Instead of going for the messy ”I just rolled out of bed” look, girls should concentrate on being more polished from head to toe: great hair, rockin’ frocks, and awesome shoes. Turn a few heads!


Photo: Courtesy of James Sims III
6 of 10
Jerrod Melman, Restauranteur

Do: I don't think I'm alone in saying I love when the winter coats come off and everyone can wear less layers. Everyone just seems happier. A well-fitting tank top tucked into a skirt is always really sexy.

H&M Skirt $12.95, available at H&M.

Don't: One thing I hate are jumpsuits. Love rompers, hate jumpsuits. It just looks weird. Same thing with jeans without back pocket. I never find that to be flattering.

Wallis Petite Black Animal Jumpsuit, $78, available at Wallis.

What should Chicago girls try more often?
Girls always come to our restaurants and clubs so dressed up and its extremely sexy. But during the day and when I'm not at work I love to see people that can make casual look good too. So I guess I want to see more done up at night and more casual during the day.


Photo: Courtesy of Henson Consulting
7 of 10
Kevin Aeh, Style Editor

Do: I love a girl in a blazer. Fitted or oversized. With jeans or a skirt or whatever. It's smart and sexy. And I kind of like the dark frame glasses I've been seeing on a few Chicago ladies lately. Wait. Am I describing Tina Fey? I do love her.

Topshop Structured Blazer, $130, available at Topshop.

Don't: Luckily I don't see this all the time, but bare midriffs are a pet peeve. I'm talking about tight baby doll shirts. Unless you're a pop star, it's not a great look. (A flowy crop top that shows off a little skin can be ok, though).

Nasty Gal I Hate Mornings Crop Tee, 60, available at Nasty Gal.

What should Chicago girls try more often?
Let's mix a little more vintage in your wardrobes, ladies!


Photo: Courtesy of Kevin Aeh
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8 of 10
Tim Toomey, Interactive Marketing Strategist

Do: I love seeing Chicago girls wear clothes that are comfortable, but also flattering to their figure like summer dresses, or even nice fitting jeans with high boots in the winter. (Steer clear of the mom jeans).

Edun Diamond Printed Dress, $592, available at Boutique1.

Don't: Big boots with dresses that are unflattering to any women's figure, giant sunglasses, huge scarves that don't match anything, enormous purses, and cowgirl hats.

Monki Everyn Sunglasses, $13.16, available at Monki.

What should Chicago girls try more often?
One thing I'd like to see more of would be tight-fitting jeans that don't look like hipster skinny jeans. The skinny jeans have a tendency to make even the most skinny girls look like they barely fit. On top of that they don't look comfortable. How do you bend your knees?!


Photo: Courtesy of Tim Toomey
9 of 10
Mig Reyes, Designer

Do: You know, I love the scarf look. It's a simple, yet versatile accessory. It's a glimpse at your personality and sophistication. Chicago is lucky to have four seasons, and seeing how you work both the material and your knots, can really tell people you know how to work it, work it.

Heart Heart Heart Printed Scarf, $565, available at Opening Ceremony.

Don't: Hate is a strong word, which is why it's perfect in capturing the world of rage that brews inside me when I see girls wearing running shoes with jeans. Listen, unless you're a mother-of-seven running a grocery store marathon, the running shoes with denim look is never appropriate, or attractive. It's an awful look for men, and you can bet it's not a good look for women, either. Bonus hate: the more faded your jeans, the worse the outfit.

adidas Women's Supernova Glide 4 Running Shoe, $104.95, available at DSW.

What thing you'd like to see more often?
I'd like to see more UGG stores go out of business.


Photo: Courtesy of Mig Reyes
10 of 10
Matt Roan, DJ

Do: Jeans and a T-shirt. I don't need any frills.  A good pair of jeans and a white tee go a long way on a woman.  A ponytail takes it to the next level.  Love a good pony.

Current Elliott The Stiletto printed cropped mid-rise skinny jeans, $170, available at Net-A-Porter.

Don't: Harem pants and kitten heels.  I know the harem thing was cool again for a minute but honestly, a saggy crotch is never a good look.  Also, if you are going to wear heels, wear them.  Don't wimp out with that training wheel business.

Romwe Tie Dyed Harem Pants, $97.99, available at Romwe.

What should Chicago girls try more often?
Girls on bikes.  Its the must-have accessory for summer in Chicago.  I swear a girl on a bike is at least 20% better looking.  I don't know why, it's just true.


Photo: Courtesy of Matt Roan
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