Personal Styling

"It is both delusional and stupid to think that clothes don’t really matter and we should all wear whatever we want. Most people don’t take clothing seriously enough, but whether we should or not, clothes do talk to us and we make decisions based on people’s appearances."

If you don’t look the part, no one will want to give you            or             .



We keep a record of everything that works for you, noting fit, colors, brands, etc. Your measurements are kept on file and adjusted as needed. After your first session, we can get new, curated clothes for you at a moments notice, or design custom garments without the need for you to be there in-person.

Ongoing relationship


After your initial consultation, we'll get a large selection of clothing ready for you at the ULCC or your home, in different sizes and styles. All you have to do is try it on. Keep what you love and let us take care of the returns and any tailoring to perfect the fit.

First styling service


The most important element for successful styling is getting to know you as an individual. Your initial consultation allows us to do just that, and it's quite fun! You'll find this to be very relaxed and enjoyable. We like to goof off.

Come into the Union League Club of Chicago (ULCC) and we'll have a drink, take your measurements, analyze your color palette and discuss your goals. The initial consultation lasts around 2 hours. We can also come to your home, and even provide a complimentary wardrobe analysis - if that's what you need.

Initial consultation


Also easy Peasy Lemon Squeezy

The GPS Personal Styling Process

If you've got lots of clothes you already love, then we can come to your home and show you how to make the most of them. We optimize your wardrobe for fast and efficient decision making and sell or donate what you don't want.

If your clothes are looking a little under the weather we can restore, repair and update them - we don't handle your dry cleaning though! Want to change the color of your shoes, taper the leg of your jeans or alter your suits? It's all part of what we can offer.

A closet full of confidence

Wardrobe Styling by GPS

Your personal style is a journey full of twists, turns, and forks in the road. It changes because you change. Men with style are great because they have a sense of self. People always ask us what the latest fashion trends are, but we're not believers in trends. Individuality is more important to us, to stand out and have the confidence to wear something you're comfortable in - we help make that happen.

Let us guide you along your journey. It takes time and it will continue to evolve over that time. You'll learn about yourself, what you really value, and how not to give a damn what others think.

you use gps on journeys, this is no different

It's not an overnight thing

As part of our offering, we can include many complementary services. As we’ve been styling and working with clients for the better part of a decade, we've built up an enviable list of Chicago’s (and around the country) best suppliers in: hair styling, eye wear, shoe repair, shoe shining & recoloring, as well as many others. Don't be afraid to ask how else we can help.

Not only that, but along the way, you might find surprise clothing or shoes arriving at your door. Who doesn't enjoy surprise gifts along the journey?


extra stuff by GPS

We’re happy to be your stylists forever, especially if you don’t like shopping, but we’ll provide tips and tricks along the way so you can do this on your own.

Learn how to shop for your body type, what colors are best for your skin tone, what closet staples are most important, how to mix colors, patterns and styles, how to accessorize, etc. You will walk away from the experience feeling more confident than ever before. It’s like a little style graduation.

Know first who you are, and then adorn yourself accordingly.

Education by GPS

Our passion for clothing and style is contagious. We love that our clients regularly call with questions, or text and email pictures so that we can continue helping with every style decision — like deciding if something matches, choosing the perfect outfit to nail the look for a big meeting or date, or just sharing how you crushed it.

We have a record of everything that works for you and what doesn't, so we’re always here to help. So if you need new shoes, shirts or a vacation wardrobe for example - we've got a record of what works best for you. Call or email us and we'll handle your new clothes, altered and delivered without you stepping foot in a shop.

Did we just become best friends? Yup!

Quoting an amazing movie,