Stylish Handbags: Color, Shape and Comfort Explained

Work-away bag. Big enough for a laptop and efficiently styled with organizational compartments, updated bags like the Baggallini Nolita Laptop Tote Bag in Ganache Twill, French Navy Twill and Black Twill ($165, nordstrom.com) are a ready-to-go office essential. Look for wide, easy-carry straps, a flat, structured base (so the bag stands straight on a desk or the floor), padded laptop pockets (most work bags now fit a 16-inch laptop), secure pockets for essentials and easy access to your cell, keys and ID.

Billowy bucket bags. More structured than the hobo but with a similar roomy, “toss-it-in” attitude, bucket bags are back again. This time around, they’re updated with open tops and a magnetic closure rather than a drawstring, like the Gap Women Vegan Leather Bucket Tote Bag in Red Spice ($70, gap.com), or a belt to provide some “scrunch” closure, like the Tory Burch Romy Bucket Bag in Tiramisu Leather, Light Cream Leather, Dark Cocoa Suede and Black Leather ($395, bloomingdales.com) with a removable crossbody strap.

Weekend/commuter/carry-on bags. A hybrid of shoulder bag, tote and luggage, multitasking bags like the Quince Transit Quilted Duffle Bag in Charcoal, Black or Navy ($120, quince.com) and the Vera Bradley Miramar Weekender in Nylon in Navy, Green or Black ($88, verabradley.com) cover all your getaways. Look for a lightweight but sturdy water-resistant fabric, multiple pockets, top handles, plus an adjustable shoulder strap and easy-access exterior pocket.

Flexible evening bags. Remember trying to cram a structured clutch with your cellphone, keys and makeup? Or trying to hold a drink and your bag while mingling in a crowd? Dumpling-like soft bags with removable dressy chain straps, like the Aqua Irina Evening Clutch in Gold ($118, bloomingdales.com) and Madewell Women The Drawstring Clutch in True Black, Garnet Stone and Chocolate Raisin ($115, madewell.com), are game changers. Not only will your mini perfume spray and mints fit, you’ll also never leave your phone behind.

2. Select a size that makes sense

(From left) H&M Women Shoulder Bag in Beige; Ann Taylor Woven Drawstring Bucket Bag in Dark Chocolate; LC Lauren Conrad Presley Convertible Tote Bag in Gibson Green.

AARP (H&M, Ann Taylor, Kohl’s)

Many women buy an everyday bag that’s way too big and then fill it with too much stuff. That combination causes neck, shoulder and backache and exacerbates the poor posture that’s already a work in progress thanks to walking while hunched over cellphones. Daily “essentials” have grown from a wallet, phone, keys, sunglasses, lipstick and tissues to also include eye drops, sunscreen, a hearing aid case and charger, a portable phone charger and/or AirPods, an e-reader, a pill container for meds, dental floss, a hairbrush and elastics, and often a water bottle and snacks. In other words, everything.

My advice? If you’re a “collector,” aim for a medium to large size — never oversized —  and reduce the contents. There’s a difference between large and too large, and photos are often deceptive. Check the dimensions and any photos with a model for an accurate read on size. Some brands and retailers label a medium bag as “large” or “small,” and vice versa.

Take a look at a few “healthy” large-enough bags, like the H&M Women Shoulder Bag in Dark Brown or Beige ($45, hm.com); the LC Lauren Conrad Presley Convertible Tote Bag in Saddle, Bethanne Brown, Gibson Green or Black ($55–$60, kohls.com); the Ann Taylor Woven Drawstring Bucket Bag in Dark Chocolate ($158, anntaylor.com); and the Rebecca Minkoff Megan Leather Hobo Bag in Black ($170, nordstrom.com).

3. Match a bag to your personality

(From left) Mellow World Robyn Hobo Bag in Navy; A New Day Kate Tote Handbag in Black; Loft Bucket Bag in Cognac.

AARP (Kohl’s, Target, Loft)

Not every bag you fall in love with will end up being a good sidekick. Think of it as dating: Looks matter, and you might swoon over the brand, color and style initially. But if that bag doesn’t suit your daily habits and wardrobe, it will end up in a bag divorce on the shelf in your closet.

Some women are what I call “bag casual.” They prefer unstructured hobos, bucket bags and totes. Bags like the Loft Bucket Bag in Cognac and Ivory ($70, loft.com) and A New Day Kate Women’s Tote Handbag in Black or Brown ($30, target.com) with an easy “throw-in” attitude mean just reaching in for keys, gum, glasses or a cellphone.  A magnetic closure or snap is enough security for them.

Others are what I call “bag formal.” They prefer more structured bags, such as the Vince Camuto Quilted Leather Shoulder Bag in Red ($228, nordstrom.com), which have specific pockets. Some bags are slouchy and structured, like the Mellow World Robyn Hobo Bag in Latte, Navy ($84, kohls.com), with plenty of compartments and pockets, plus a secure flap or zipper closure. Regardless of style, many bags come with a variety of straps that allow you to shift its weight from shoulder to crossbody to hand-carry in seconds, or have zippered outside pockets or key chains for easy access to important items like your keys and phone. Make a list of your own priorities and preferences before shopping.

4. Pick a color with benefits

One of the biggest bag decisions is choosing the right color. Some women buy a bag that matches their shoes and the top neutral colors in their closets. They think, “Well, I wear a lot of black, so a black bag makes sense.” The same applies to brown shoes and bags. Matching hues of shoes and bags does create a pulled-together look, especially when paired with complementary colors in your clothes. But that doesn’t mean that black or brown bag works all year round.

For example, a black leather bag may be great in January but too heavy in color in July, when you’re wearing more white, pastels and brights. A lighter, neutral color like tan, camel or beige is a smart seasonal swap.  And sure, you can wear warm neutrals, like the Cuyana Classic Easy Zipper Tote in Stone and Cappuccino ($328, bloomingdales.com); the Quince Italian Suede Slouchy Shoulder Bag in Pebble and Sand ($150, quince.com); and the Old Navy Women Large Belted Tote Bag in Toasted Almond ($50, oldnavy.gap.com) all year round, or as “spring-summer” bags. These colors also work well with all warm and cool neutrals, including black and navy.

Also consider a bag in a rich olive or taupe, such as the Vince Camuto Aleah Suede Tote in Dark Taupe or Reishi ($248, nordstrom.com) or the Fossil Willa Leather Medium Shoulder Bag in Green ($195, macys.com), to accent black, brown, gray and navy.

If you’re choosing between several bags, one dealmaker method is to check the hardware. If you wear mostly silver jewelry, silver-toned buckles and closures look better. If you wear mostly gold jewelry, gold-toned bag hardware keeps the warm gleam going.  Still unsure of the bag color? Here’s my foolproof solution I suggest to all:  Buy a bag style you love in a new-for-you color, or buy a new-for-you style in a “safe” neutral wardrobe color like black, brown or tan. 

5. Choose a body-friendly bag

(From left) Madewell Women The Sculptural Buckle Shoulder Bag in Dark Burgundy; Donna Karan New York Cashmere Crossbody Bag in Sand; Adornia Slouchy Shoulder Bag in Brown Suede; Universal Thread Curved Shoulder Bag in Black.

AARP (Madewell, Macy’s, Kohl’s, Target)

Your bag should work with your shape, and where any bag “sits” on your body matters. A shoulder or crossbody bag that rides very low on the hips or thighs — especially a sharply structured bag — increases body width at that point, so you look wider. In addition, the low “hang” makes it challenging to access essentials and often produces a painful and annoying bump-and-bounce effect as you walk.

Choose softly shaped styles that conform to body curves, sit higher on the hip and tuck neatly under your arm, like the Universal Thread Curved Shoulder Bag in Gray, Burgundy and Black ($16, target.com) or the Adornia Slouchy Shoulder Bag in Brown Suede ($60, kohls.com).

If you’re on the busty side, your neck and shoulders are already dealing with the weight of heavy breasts. A lighter, smaller, curvier bag in a soft, buttery leather, such as Madewell Women The Sculptural Buckle Shoulder Bag in True Black or Dark Burgundy ($168, madewell.com), will complement your shape. And let’s talk bellies. One of the secret pleasures of a crossbody bag, like the Donna Karan New York Cashmere Crossbody Bag in Sand or Cloud Gray ($258, macys.com), is that it helps camouflage a belly bulge. Just make sure it isn’t too large, or you’ll be emphasizing, not minimizing.

6. Give your new bag a road test

Is your new bag a keeper or a return? Transfer all the stuff from your old bag to the potential newbie. Then slip on the bag and look in a full-length mirror, either in the store or at home. Check how it looks and feels by trying it over several outfits, including jackets and coats. Look at the side, back and front views; both sides, too. Does the bag feel comfortable, or will you need to constantly adjust or shift the strap? Try walking around. Are you bending your head and neck forward as you walk, or hunching your shoulders to keep the bag in place? Is the bag bouncing around as you move? Can you quickly get to your phone and keys without removing the bag? Give it a 24-hour rest and try again to make sure. By then you will have overcome the initial attraction and become a tougher critic.

7. Be realistic about affordable style and quality

The idea persists that an expensive bag, such as a Louis Vuitton Neverfull tote or a Gucci Softbit Shoulder, conveys good taste and status. While those bags and others in that category are well-made and beautiful, let’s be practical. If it’s a choice between spending $2,000 on a new bag or $1,000 on a pre-owned, vintage one and paying your HOA or health insurance, or taking a weekend getaway, would you buy the bag?

My advice: Don’t underestimate low- and medium-priced bags. Many low-cost bags now mimic the look and features of high-end ones. Those in upscale neutral colors and excellent faux leathers and faux suedes (which bring down the cost) do look sophisticated and more expensive. However, many bags, available in all price ranges, look great online but often disappoint in person. Pay attention to buyer reviews and photos.

Here’s what to watch out for: You want to see perfect, even stitching, with no loose threads; hardware that’s matte or at least not too shiny; buckles, zippers and latches that close and undo easily; and most of all, minimal distractions like extra embellishments that disguise poor-quality material or workmanship. And regarding those luxury bags, in my opinion, women over 50 already possess plenty of attitude and status, so there’s no need to spend thousands of dollars on a bag to achieve it.