Every year Goodwill Industries of Southeastern Wisconsin and Metropolitan Chicago hosts its biggest fundraiser of the year called Retro Rendezvous. This year the event will be held on October 29th at Potowatomi Bingo & Casino in downtown Milwaukee. Included in the evening’s festivities is a fabulous sit-down dinner, a silent auction with lots of awesome donation items, and a professional stage show featuring national acts. There’s also a runway show highlighting items from Goodwill’s very own clothing archive, as well as current fashion trends from Boston Store. Present and past members of the Green Bay Packers and their families also make celebrity model appearances. What an evening it is for those who attend, and especially the folks who bid on and win some of the great products and services offered in the silent auction!

Since I have had the honor of doing work for Goodwill, I have donated my fashion services to the silent auction. Last year this included a shopping trip with me as your personal style advisor, and a $100 gift card from Goodwill. I know first-hand how hard it is sometimes to shop for clothing, because we all tend to stick to “what we know” and focus on the negative rather than the possibilities of thinking outside the box. I thought you might like to hear about the haul last year’s winning bidder, Julie, made with a few of my tips and tricks of the trade.

When Julie emailed me, I asked her a few simple questions. What is lacking in your current wardrobe? What are your trouble spots when it comes to fit? Have you done a closet clean out recently, so you can focus solely on what will work with the existing clothes in your wardrobe?  I also had her bring along a pair of heels that she would wear with dresses, and to dress comfortably for lots of trying on. These are key things when wanting to make the most of a shopping trip to Goodwill.

We made a plan to meet at the Palmer Street Store one evening last week and spent a few hours scouring the racks for perfect additions to round out the looks that she loves. I explained my strategy to her. First, I would look for dresses, while she focused on slacks and skirts. Then we’d both work on looking for accessories and jackets. Once we had a plan, we put it into action. With $100 to spend I knew we could really make a haul!

Like many people, Julie’s problem area was slacks and jeans. Being taller, and having a fuller figure, it’s often difficult to find pants that fit properly in both the waist and the length. My suggestion was to first zero in on other items that would work in her professional wardrobe (like skirts and dresses) that she felt good in and flattered her shapely legs. By trying on those items first and finding quite a few that she liked, her confidence level grew. So, by the time we did try on some slacks and jeans, there wasn’t the frustration that sometimes happens when trying on harder to fit items. I suggested that having a nice pair or two of slacks tailored to fit perfectly are preferable to owning lots of pairs of pants. 

Jackets are always a great way to step up your style.  A nicely fitted coat can be worn with dresses, blouses and skirts, jeans, and more. We found a lot that would easily work into her professional wardrobe as well as add some life to casual pieces, too! 

When it came to shoes we had a challenge because knee problems don’t allow her to wear much of a heel. Not a problem, because loafers, and smaller heeled shoes are all the rage in fashion right now! We set right out to try on as many as we could find in her size. 

Are you noticing a pattern here?  Try on, try on, and try on some more. Keep an open mind to what you perceive as your flaws, and focus on the things that truly flatter you! In the end, this is what Julie got for a grand total of $85:

• Jones New York - denim dress (favorite)
• Adrianna Papeli - purple formal mini dress (favorite)
• Ann Taylor - pinstripe dress slacks
• Black and white hound’s-tooth high wasted pants
• American Eagle - dark washed distressed jeans
• Ann Klein - brown mini skirt
• Blue cotton skirt
• Vintage - long grey blazer
• Ann Klein –black and brown textured jacket
• Chaps – cream and brown pinstripe pants w/matching jacket (favorite)
• Franco Sarto – blue leather loafers
• Franco Sarto  - brown leather pumps
• Talbot’s  - NEW cream leather slides
• Vintage - ivory Mary Jane-style shoes with cut out details

Even though you may not have me helping you to make shopping decisions, you can utilize some of my expert tips! It’s a sure-fire way to be a big winner when it comes to refashioning your wardrobe for less at Goodwill.