Anna L. Loess

Awards & Recognitions

• Public Interest Law Initiative Fellowship Recipient
• Best Lawyers® – Best Lawyers in America – Family Law, Trusts & Estates (2024, 2025)

Client Recommendations

An excellent and fierce advocate – “I retained Attorney Anna Loess to help me navigate modification of custody and secure impasse authority, related to services for my children, including a special needs child.  Anna was incredibly compassionate and understanding of our family situation. She provided excellent guidance and candid assessment of the circumstances. I always felt certain she was fighting not just for me, her client, but also for my children's well-being. She was very thorough, communicative, and responsive during a multi-month process.  I would turn to Anna again without hesitation if I need legal counsel in the future. I have recommended her to a colleague and a family friend, because I wanted them to have to best attorney in their corner.” – Child Custody Client

Winning! - “A very kind, understanding and THOROUGH person Anna certainly is! She gets the results you want! I am extremely happy that I chose Anna for representation! – Probate Litigation Client

Probate litigation – “As personal representative for my brother's estate, I hired Ms. Loess to object to a claim made against the estate. She was so skillful we didn't have to defend our objection. She was willing to travel to another county and always kept me informed of my options and obligations. A positive part of a negative experience.” – Probate Client

Highly recommended – “I hired Attorney Loess after my ex-husband filed a motion to modify child support. Attorney Loess supported me through the process by clearly explaining my options and the steps I needed to take to ensure that minimal or no changes were made to my child support payments. She worked hard for me and the outcome of this case was better than I hoped for. I have and will continue to recommend Attorney Loess to friends and family.” – Child Support Client

Divorce – “Anna is the type of lawyer that works for her client. When my ex tried to take everything for himself Anna proved to him that it was not going to happen. She worked hard to making sure the laws were being followed correctly. She was very helpful telling me what were my choices and what her thoughts were on how we should proceed. She was very knowledgeable and sympathetic when other parts of my life were in need of my time...” – Divorce Client

Excellent, respectfully compassionate – “Anna was my attorney for a divorce and was simply excellent. We settled after some thoughtful, careful negotiation by Anna. Her filings and legal work were excellent, and her communication was superior. She gave excellent and compassionate legal advice; she is experienced and knowledgeable. As an attorney myself, I know I was well-represented. Equally important to me, however, was her consistently respectful and patient attitude...” – Divorce Client

Made sure the attorney was the least painful part of divorce case – “Anna was great to work with as my attorney for a divorce case - she always made sure I understood my options and helped me decide what would be best for me. She always suggested ideas for different approaches that might make things work better. Not being familiar with legal processes myself, she made sure I understood was expected of me and made it simple, while taking care of most communication and logistics quickly and efficiently.” – Divorce Client

Anna is the lawyer you want at your table. Fearless, thorough, thoughtful, intelligent, articulate and understanding – “My divorce was complex and difficult. Anna always had my back, helping me through the confusion of divorce. Her attention to detail and her knowledge of family law and business law helped me to avoid many of the pitfalls that are hidden throughout a complex divorce. She will call out shady or questionable actions, she does not suffer fools and she doesn't mince words. That said, she is also sensitive to how emotionally devastating and...” – Divorce Client

On our side and never stopped fighting for us! – “From the beginning Ms. Loess recognized that we had a case, and demonstrated by her actions that she would do all that she could to help us protect a vulnerable family member from potential elder abuse / exploitation. She walked the extra mile in a timely way, even uncovering things of which we were not aware Her modus operandi is "action." – Elder Law Client

Attorney Loess - attention to detail – “I have used the services of Attorney Loess twice, first to make a Durable POA and Trust/Will and then later to make substantive changes after a life event change. In both cases she had great attention to detail, thought of things I never would have, and made sure all the possibilities were covered. She also made sure that the revised documents had the newest recommended wording. I would use her services again if I needed more changes or new documents.” – Estate Planning Client

Client who is also an attorney – “Anna handled my complicated case in a very skilled, professional, and compassionate manner. My only regret is that I didn't contact Anna earlier in the process, which could have improved my situation. I would happily use Anna's services again if I were in need.” – Divorce Client

Elder law issues – “Anna has represented our family member with dementia for the past five years. During this time she has dealt with powers of attorney, guardianship and elder abuse issues. She's been a fierce and compassionate advocate and has guided the family through some very difficult times. We continue to seek her advice and rely on her judgment.” – Elder Law Client

Excellent lawyer! – “ I highly recommend Anna as an attorney. Anna is extremely competent, professional and honest in her work. My sister and I hired her to help with a probate matter. Anna clearly explained our options, quickly responded to all communications and helped us navigate a very difficult family situation. I was impressed with Anna's work to validate our claims and found her to be above reproach. She was also compassionate, understanding and kind.” – Estate Planning Client

Family litigation – “Anna helped us through a family litigation that was very difficult and emotionally draining. She was very compassionate and always quick to respond through phone and email. She made us feel taken care of and protected. We highly recommend Anna and are grateful that we found her.” – Family Law Client

Divorce – “ I had the pleasure to work with Anna for my divorce. She made everything quite simple. Great communication via phone and email.” – Divorce Client

Excellent divorce lawyer – “Anna Loess is an outstanding lawyer. She is very knowledgeable and laid out all possible scenarios in my divorce case. She was easy to work with yet stood her ground when needed and would have been a formidable defender of my case if it had been necessary. My long working hours required flexibility and she communicated electronically to accommodate me. I highly recommend Mrs. Loess for divorce cases.” – Divorce Client

Estate planning excellence – “Anna was recommended to me with much praise of her expertise. She was extremely knowledgeable in the trust planning for my parents and my disabled brother. From the onset of understanding our needs and wishes to the implementation of writing the trusts that would secure the future needs of my parents and long-term financial needs of my disabled brother. Her insights were invaluable, and her people skills were excellent.”  - Estate Planning Client

Exceptional attorney! – “Anna Loess helped me navigate probate issues during a very difficult time in my life. She was very patient while being clear and concise. She is extremely knowledgeable and was prompt with responses to all my questions and concerns. She explained my options and possible outcomes with kindness and reality. I was able to proceed with confidence because of her expertise. I needed an advocate and advisor for my legal matters, and she is beyond a doubt the right choice.” – Probate Client

Divorce – “A complicated case because my sister was diagnosed with Alzheimer's shortly after she was married. Her husband filed for the divorce. Anna was knowledgeable, thorough, and compassionate. She not only protected the rights of a person who couldn't take care of herself, she gave her entire family peace of mind and the ability to take care of her for the rest of her life.” – Agent of Divorce Client

Family law rock star – “Anna joined the team managing the wrap up of my parents' estate. There was a family power struggle that had ground all progress to a halt. There were very complex legal dependencies involved in the wrap up along with some stubborn parties. Anna applied a balance of creativity and structure, utilizing a balance of velvet gloves and an iron fist to deal with interpersonal conflicts among the parties.” – Estate Planning Client

Anna Loess – “I worked with Anna on a very difficult family law issue and was impressed and grateful for her thoroughness and grasp of the issues. She's very detail-oriented, doesn't miss a thing, and was extremely effective at untangling - then explaining - the nuances of my case.” – Family Law Client

Clients

Anna’s client base is diverse, and they come from many walks of life.  While a first year law student at DePaul University College of Law in Chicago, Anna capitalized on her social work background and began volunteering at the Chicago Legal Clinic, a non-profit organization that provides legal services to clients who are not eligible for no cost legal aid services, but who do not have the resources to pay for private counsel.  She was subsequently awarded a Public Interest Law Initiative fellowship and continued to provide legal services to an underserved population of clients at the Clinic through the remainder of her law school career.  She was hired by the Clinic as an attorney upon her graduation from DePaul.  While employed at the Clinic, she represented clients in various types of family law matters, matters involving domestic violence issues and at disability hearings before administrative law judges of the Social Security Administration.  Upon transitioning to private practice in the Chicago area, Anna continued to represent individual clients in various family law matters, as well as individual and business clients in commercial litigation cases.

Upon her relocation to Wisconsin in 2009, Anna continued to represent clients in a variety of family law matters, and she expanded her practice to include the representation of individuals and corporate fiduciaries in probate and trust administration and litigation matters, estate planning and elder law matters.  As a dually licensed attorney, Anna has assisted Illinois attorneys and clients with Wisconsin legal matters and has assisted Wisconsin attorneys and clients with matters that require expertise in Illinois law.

Service Area Subspecialties

• Family Law
• Appeals
• Child Custody, Placement & Support
• Divorce
• Elder Law
• Guardianships
• Prenuptial and Postnuptial Agreements