How I Choose A Handbag

Do you carry the same bag every day until it falls apart? Choosing a bag to complement your look can complete it and pull everything together with finesse or add a punch of color with your neutrals.

“How do you decide which color, type, and size of bag to carry when you change them so often?” It is a question I often get, so today; I will share what I consider when deciding which bag to carry.

I chose a woven black leather clutch to tie in with the top and the necklace in the photo above. Working with three pieces that relate in color helps to pull a look together. The bag’s style usually relates to the style of the shoes, but I don’t typically match the color. Unless you are wearing a monotone look, it is more modern to carry a bag that is a different color than your shoes. (I always try to wear shoes that visually lengthen my legs.) Here I am wearing Valentino Rockstud inspired pumps, which required a more sophisticated bag.

Sometimes I use a bag to add a pop of color and add a scarf to include some pattern to an otherwise monotone look of all black. When wearing all one color, always vary the fabric textures. You never want it to appear that you tried to match the colors but failed.

When we go out in the evening, I switch to a small clutch, which relates to what I am wearing. The leather jacket required a more geometric blanket scarf rather than a silk print. I followed the same path when I added the studded box clutch. All of the elements of my look have a more urban edge to them, so they relate to each other. Keep all of the items in the same tribe.

I rarely carry a shoulder bag, but it is slim and structured like this one when I do. Nothing ruins the line of your clothes or makes you look more substantial than a big slouchy shoulder bag.

A classic Chanel-inspired chain bag with a quilted texture could work with almost any look.

I am wearing comfortable flats with a hands-free crossbody bag in the photo above, so I was likely going grocery shopping that day. Notice that basic neutral pieces can easily be combined to create smart-looking outfits without much effort going into the process.

The colorful clutch above was out of my comfort zone. I have rarely purchased a bag that included so much color and texture, but I carried it often last summer. I wear one or two of the colors in the bag and then let it be the star of the show. This clutch’s texture and attitude say casual summer, so I put it away for the winter months.

A straw or rattan bag always says summer to me. Those, too, are put away in the colder months.

Large suede-trimmed or reptile embossed bags are for the daytime and serve me well when traveling in the colder months. I always think of these textures as winter accessories, whereas I think of patent leather for springtime.

A top handle satchel in a light neutral color serves me well for regular daytime use, as shown above. In summer, it is often a light tan color. In the winter months, it might be a light gray, as shown below.

Last year, I did a video on how to organize the contents of your bag here. This trick allows me to change my bags often since I can grab what I need for the day.

The clothes and accessories I show you are from my collection, so that means you will see the same items again and again, hopefully, combined in different ways.

  1. Love you and your blog! I do have a quick question for you, where did you purchase the nice looking white blouse you have on in these pictures and also the knee-high boots. I’ve been looking for a casual three-quarter length white blouse and I’ve also had trouble with finding a pair of knee-high boots that was zip up over my calf. My calves are not exceptionally large but it seems to be an issue I’ve had. Thank you.

    1. The white blouse was from Cali and York last year. They often have a similar style available. The over-the-knee boots have an elastic panel in the back which is the only reason I can get them over my thick muscular calves. They are by Vince Camuto from last year.

  2. Thank you. A very helpful lesson. I use a bag organizer that I can take out and put in another bag but I like the idea of smaller separate bags because my organizer doesn’t always fit if I am switching to a smaller bag.
    I noticed something today that I haven’t noticed before and it has nothing to do with today’s blog but in all of these photos you have on a light blue jean. Do you prefer the light blue to the darker when you where blue jeans?
    I follow several blogs but yours is my favorite. For my age you give wonderful tips that have helped me so much. I have not attained your class in style but I am learning and hopefully improving.
    Thank you.

  3. Great advice on selecting the best looking bag for your outfit. I like your statement to keep all the elements in the same tribe. When I worked in a business environment, I purchased some beautiful leather bags (and one Gucci satchel I loved with a bamboo handle) and these have held up wonderfully. Buying the best quality you can afford will always be the best buy to make. Living in NYC, we basically carry our lives with us daily since no one has a car to put things in and we are often gone from morning to night. Many carry several bags and totes with them and this can lead to a sloppy look. I recently received for my birthday a great black Coach tote which really solves this problem by enabling you to look neat and yet have room for daily needs.

  4. I too change my handbag frequently and often use it as a pop of color, so I was very interested in your perspective. I watched the video on organizing the bag contents (I do something similar, not as perfectly organized as you!) and was happy to see that you have multiple videos available on youtube. Thanks so much for all the work you put into sharing your knowledge.

  5. I love handbags, but, rarely take the time to change them out because of the time involved. I just watched your video on organizing your belongings in a handbag and I am excited to replicate your approach. How streamlined, neat, and simple! Thank you so much, Becky

  6. Hi Susan, I would like to thank you for all the wonderful ideas and suggestions that you share with us. Since finding your sweet Blog I have changed the way I look at my clothing in my closet and the way I shop for new items. I stopped coloring my hair about 14 years ago and have received many compliments since then. I love that I’m not alone and that there are a lot of us out there who mustered up the courage to go natural. I love your color and cut, it suits you so well. Thank you for your videos, I always enjoy them. Enjoy your day!

  7. You keep me aware! Joy in the moment, no matter the age. I am so happy to have found your site.

  8. Hello Susan…Thank you for sharing all your tips. I’m learning a lot about dressing simply but appropriately for different occassions and healthy eating.

    I have two questions:

    I began a vegetarian diet…no meat, fish, or chicken. Whole foods in their natural state. I’ve lost weight and still have a lot to go but my arms are very crepy and saggy and I can’t wear sleevless or short sleeve tops. I don’t like tight clothing. What do you suggest that would work for me to take me from casual, work, and evening. How do I incorporate tops that won’t be bulky if I wear a sweater or jacket with it and still feel comfortable.

    You wear shoes that lengthen your legs. I have short legs too but I don’t wear heels right now because of my weight. I did see your video on shoes. Do I wear pointed flats to lengthen my legs? Also, can I wear longer tops with flats or will that make me look shorter?

    Thank you for all your amazing blogs and videos. I live vicariously through you. ♥

    1. Hi Linda. I know exactly what you mean. I have lost weight so many times in my life, I feel like a deflated balloon that has been blown up too many times. I look for pieces that are almost sheer and flowing. I balance the top and the bottom by wearing a tighter fitting shorter top with flowing loose pants. The reverse is my favorite since my legs are not too bad. Slim fitting light color pants with a dark flowing top is my all time easiest to wear look because my top half is larger than my bottom half. Wear flats with a slim fit and almond shaped or pointed toe to elongate your legs visually. I hope this helps you.

  9. I’ve noticed that you favor bags with structure. This works so well, for the overall look and for organization. It’s never fun digging around in the bottom of a floppy bag for something you need.

  10. I have followed many fashion/makeup blogs for us “golden girls” and wound losing interest them because their style was not something I could connect with. You, my dear are perfection. My slacks are black, white, beige and jeans. I wear solid t-shirt type tops,in burgundy, hunter and various blues, never pastel I layer black or white tanks with solid shirts or jackets. I wear silver jewelry, adore statement necklaces and worship scarves. I don’t see many scarves being worn since the infinity fad settled down.I’m not going to give them up ever. MY makeup (except for lipstick that pops) consists of neutral colors to look rested and refreshed. Blue and purple do not belong on my face. Your blog is so refreshing and I have learned so many ways to pull of my personal style.I enjoy your youtube videos. I would give anything to attend one of your workshops but .traveling is almost impossible for me. I am also a Tennessee girl. Keep up the good work and add lots of videos. Sisters in spirit.

  11. Oh no! Was very inspired by this post & the past video and was finally going to organize my new bag, pouches & wallet. Got the bag out & noticed the security tag was still attached on the bag. Another trip back to TJ Maxx! Bummer, but so appreciate all the good tips. Will give me time to hunt down my sunglasses case though. Hate it when that happens!

  12. The video on organizing your handbag was great! I do have a question: I know that you’re a faithful wearer of sunglasses, but didn’t see them mentioned in your video. Since sunglasses are so much larger than reading glasses, I struggle with a case that looks neat. Any suggestions?

    1. I am guilty of wearing them on my head at times, but I also have at least one pair in every car. I like the slim hard cases they can be slipped into the larger bags with no trouble.

  13. I had no idea that a shoulder bag made me look heavy! Yikes! That’s the last thing I need! I love a big purse, often kinda like a tote, because it holds so much! And I always like to have my hands free! Maybe I can start slowly with one smaller bag and see if I can adjust! Change is hard! 🙂

  14. Thank you for the great advice about the bags and the video. I was wondering if you could tell me about the tan pants you are wearing in the tenth photo. They look great on you; your legs look very long and lean.

    1. Those pants are from they are the by Lior Paris. They come in several lengths and leg shapes so that you can get what you want. Love them!

      1. I absolutely love all your purses. I like your idea of the top handled purses. I usually carry a fairly large shoulder bag or square tote. I need to go purse shopping, ha! ha!

  15. Susan, I just found your site/blog and love your taste in clothes, jackets, shoes and pocketbooks! I am 57 years old and against the advice of my friends and loved ones, I have grown out my colored hair to my natural soft pewter and silver color. You are an inspiration to me and I look forward to learning more from your posts. Thank you for sharing your insight. Tamara M.

  16. Love all your purse ideas. I am also a fan of purses and have to many but tend to use the same favourites most times.

  17. Greetings! Last year at some point you showed a large true green bag that I just loved. It was all leather, wider than tall, and just gorgeous. I wondered if you could tell me where I might buy one.

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I share tips and inspiration for using what you already have in contemporary ways. Defining words include effortless, classic, refined, discreet, and elegant. My style is chic, minimal, and timeless with a bit of edge.