Messenger meet Boyfriend

Ah, the boyfriend jean. As we so lovingly mentioned in the last post, the Terrain Messenger is not just a bag...it's an outfit completer. So what if your hair is in a ponytail and you didn't put makeup on before you set out to tackle a never-ending list of errands? You're rocking a solid, dark fitted tank tucked into a low-slung relaxed pair of denim and your Terrain Messenger - and people can only help but wonder how you managed to look so naturally put together.

Whether you have a pair of loose-fitting jeans already, or find a fabulous pair you can't live without, there are tons of ways to wear them. Keep the jeans full length with funky flats while you're going about your day. Roll them up just above the ankle and wear with comfy wedges when you meet your girlfriends for lunch.

P.S. Light washed, destroyed denim is a sizzling summer look!

Messenger meet Maxi

Remember our good friend, the Terrain Messenger Bag, and how you had absolutely nothing to wear with it? Pair a dress like this with the Terrain Messenger, flat gladiator sandals, and a wrist full of brushed gold bangles to evoke the coveted "oh this old thing?" response.

Luckily, maxi dresses are still a hot commodity and perfect for equally as hot weather. You can find them at Forever 21 for less than $30. If you want something a touch less mass produced for a few extra bucks, check out ModCloth's eclectic options.

Messenger meet Oversized Blouse

Oversized tees might be the best thing since sliced bread but isn't it time for an upgrade?

Sheer button-ups have been seen everywhere lately. They're a quality investment piece that can easily be dressed up or down. Transform your casual work wear into a sexy, yet sophisticated night look and hit the town on a weeknight! Step outside of your neutral-colored box and pick one up in a vibrant color or fun print! We're only young once, ladies.

But best of all, this black chiffon blouse is a perfect staple to wear with your Terrain Messenger. Wear it loose with your favorite skinny jeans and sneakers for the ultimate casual-cute look.

Take a break from the long weekend to check back for two more fresh looks to compliment your Terrain Messenger, our favorite Wether Bags piece coming to you at the Chicago Fashion Bash!

Summer Chic in Chicago with Whether Bags

What better way to kick off the countdown to our Chicago Fashion Bash than an introduction to Whether Bags -- the ultimate in sustainably chic handbags made to endure the elements.

Our favorite? The Terrain Messenger Bag.

It's a versatile bag that takes your go-to oversized tee and jeans outfit to boho bombshell in the blink of an eye. Not only is it easy, it's functional. As if being big enough to fit your laptop, beach read, or grocery staples isn't enough, the outer flap is lined with hand-woven ribbon. A quirky characteristic that can be seen on tons of Whether Bag's 2011 pieces.

You adore the bag. You applaud that it's going to be discounted at SCC's upcoming event. You relish in its ability to fit your nonstop lifestyle. But your wardrobe doesn't love it, you say? Not to fear, your friendly City Chick is here to help you find outfits that will love the Terrain Messenger as much as you do.

Stay tuned throughout this week for tips on how to wear the bag. Don't worry, we have a few other surprises up our sleeve for you too.

Also -- check back throughout the month as we countdown to our Chicago event with a different featured designer item and how to wear it each week.

Summer '11 Trend Accessories

In order to stand out from the crowd this summer, add these must have accessories to your wardrobe! They are not only trendy, but their prices will keep you from breaking the bank...

Kali Wrap Bracelet: $14.90

Buy @ alloy.com

Dolce Vita Rope Wedge: $29.99

Buy @ target.com

Deena and Ozzy Chain Tote: $58

Buy @ urbanoutfitters.com

Double Up Wrap Belt: $18

Buy @ francescascollections.com

Sunglasses: $5.80

Buy @ forever21.com

XOXO,

Sassy Chick