Dear Fashionista: Party In Chicago Wardrobe Help

Dear Fashionista,
Help! I’m going to Chicago in March for our son-in-laws surprise 40th. They are coming from CO with other 35-40+ yr olds. My daughter has arranged for some evenings at sports bar and Wrigley Field. What is a 60+ yr old to wear?? My daughter is an up-to-date fashion, trendy gal
– Pam

Dear Pam,
You won’t believe this but my hubby is from Chicago, and so your request for help brought a smile to my face. He’s wondering if he can come too?  Really my basic things for you are to focus on key pieces and fill in the blanks with jewelry and shoes you have if you can.

A few quick tricks to use clothing you already have in your closet. Get a few scarves, they’ll take any outfit up a notch instantly. Statement jewelry can make your outfit feel dressed up or “special” just by strategically putting some with any outfit. Make all of your accessories color your outfits. Think of your outfit as the canvas and your jewelry the paint.

Invest in a pair of trouser jeans. The great thing about these types of jeans is that they are comfortable while allowing you to feel so put together even with a t-shirt. They are flattering to all body types and can be worn with flats or heels.

For your trip to Wrigley Field I put together a simple outfit that incorporates those great trouser jeans. You’ll notice I put boots with it, but nothing with a high heel because the truth is your still in a ball park, but given the possibilities in weather covering your bases (see that a baseball pun) is your best bet. Get a lightweight cross body bag like the one below that you can throw on any outfit. Keep your bag carrying simple because you are traveling you’ll be doing a lot of walking I’m sure. Just so you know my mom who is your age has this bag in black and white polka dots, and loves it. Yes, I was there when she bought it!

Going To The Ball Game


You can see here that I took the same trouser jeans and same purse to make another outfit to just go out in. Paired with some cute flats and a beautiful sweater this outfit can be worn all day and night. Just add a stunning piece of jewelry. By making another outfit around your new jeans and bag you are making it easier to pack. This one is a great outfit to wear to the sports bar.

Going Out (For The Day or For Dinner)


Then I thought I better come up with an alternate out to dinner outfit that is paired with a skirt just in case. This skirt is still quite casual while staying chic. If you don’t like the skirt switch it out with any a-line skirt. I use the same boots from above, again wanting to focus on the packing light option.

Going Out To Dinner


For the actual festivities I thought a dress with a beautiful neckline would be a great idea. This a-line style dress is figure flattering, and produces a beautiful hourglass figure. I paired it with a kitten heel. I figure that since it is your daughter if you’re like me and my mom you’ll be running around helping her out all night. There’s no reason to be in high uncomfortable shoes. The beautiful intricate necklace is the perfect compliment to the neckline of the dress.

Going To A Party


Pam I really hope this helps you with deciding what to wear while you’re in Chicago. I’d love an update and maybe even some pictures to see how things worked out. If you need even more suggestions you know where I am.

About Fashionista

Candice Kahn has written 808 post in this blog.

Candice is a mom of 3 in Los Angeles, CA, and the Owner/Editor-in-Chief of Fashionably Organized. Her obsession with researching products to get the right price, has made her the go-to shopping guru for her friends. Here she writes about fashion, beauty and shares her love for home decor and DIY. In 2012 she began CB Media Solutions her company that offers brands and clients professional virtual assistance and social media consulting.



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