A Sharp Dressed Man

Personal Stylist in Chicago, IL

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About A Sharp Dressed Man

A Sharp Dressed Man is a personal stylist & personal shopping service for men in the Chicago area. They offer a number of services including virtual styling, personal shopping, closet edit and our favorite - date styling.

Our Analysis

A Sharp Dressed Man is our top-pick for fashion consultants in Chicago. Not only does Jennifer create incredible results for her clients, but she does so with the utmost care and attention.

A Sharp Dressed Man was founded by Jennifer Lund in 2012 after spending a number of years in the fashion industry. Today she works with men of all shapes, sizes, ages and styles to optimize - or completely overhaul - their style.

Jennifer leans into clean, timeless styles which are perfect for men who are 25+. You can see a number of her outfit combinations in her gallery, and read a number of positive reviews on her website.

Why you should trust us.

We're a team of photographers, copywriters and marketers with a common goal - make online dating suck less. We offer services to optimize your dating profiles to maximize your matches, improve your conversion rate and meet better people.

A Sharp Dressed Man Reviews

There are a number of great reviews online, but these are the ones that impressed us most:

I wanted to take the time to express my extreme satisfaction with Jennifer and her service, "A Sharp Dressed Man". We met for a quick overview via zoom then she came to purge my closet, then finally to meet with me to shop for a whole new wardrobe. I was so impressed by not only her fashion sense in the industry, but how she conducted her business. When I arrived to the store, she was already there an hour and 30 minutes ahead of schedule and had picked out several outfits for me to try on. Jennifer took down my information, purchased all of my new clothes, then delivered them to my closet. This was an experience that I was happy to spend my money and time on. Jennifer is not only very polite and personable, but her business and work ethic is a well oiled (fashion) machine. I have already recommended some of my friends to her and will contact her again for further fashion advice.
Benny L.
May 28, 2022
I did a closet edit with Jennifer, this was the first time I've ever worked with a stylist. Jennifer was great. She helped pick out stuff that was good, and stuff that didn't fit very well, then put together a bunch of outfits using things I have, and gave suggestions for things to buy to fill gaps in my wardrobe. The outfits she put together look great. She's also super efficient. Highly recommend!
Anthony Z.
March 18, 2022

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Frequently Asked Questions

What services does A Sharp Dressed Man offer?

A Sharp Dressed Man offers a number of services including style consultations, closet edits, personal shopping and our personal favorite - date night styling.

How much does personal styling cost?

A Sharp Dressed Man offers 3 levels of packages ranging from $75 for the starter package, to $800 for the VIP package.

Does A Sharp Dressed Man offer services for women?

While Jennifer has built her brand around working primarily with me, we did see a number of positive reviews from women in Chicago.


Founder Name
Jennifer Lund
Provider Type
Personal Stylist
Zip Code
Service Type
Average Rating
+ Reviews
Price Range

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