I have always loved the look of a stiletto heel. In fact, I remember when I had started my first "real job". I finally had money to buy expensive shoes. I saved up to buy the shoes I'd been drooling over, a pair very similar to the Christian Louboutin So Kate Pump. They were everything I thought I wanted -- a sleek shape, a towering stiletto heel, that unmistakable red bottom. I knew they would look awesome with both skirts and pants. However, there was one minor detail that prevented me from keeping them. I couldn't walk! Despite their beauty, they were incredible painful. Sadly, they were returned.
When I am working with a new client, they are often scared I will recommend they purchase a plethora of sky high heels. This is never the case. In fact, most of my clients' ask for comfort first with their footwear. Fortunately, there has never been a better time than now to shop for shoes that are both stylish and comfortable. My favorite brands for comfortable, chic heels are Cole Haan, AGL, Clarks, Ecco and Naturalizer.
Naturalizer Almond Toe Pump, $89
AGL Studded Mary Janes, $380
Ecco Suede Block Heels, $129
We all know the lie of "comfortable flats"--shoes with no heel should automatically be comfortable right? Wrong! These styles lure us in with their false promises of pain-free days only to betray us with a lack of arch support. My favorite flats come from Talbot's, Lucky, and Born.
Born Ballet Flats, $90
Lucky Flats, $59
Born Flats, $90
While not appropriate in all professional environments, wedges can be a great option if open toes or sandals are permissible in your workplace. If not, you could still opt for a closed toe wedge. I enjoy Sofft and Cole Haan wedges the most.
Cole Haan Wedge Pump, $101
Sofft Gladiator Wedge, $100
Cole Haan Sadie Open Toe Wedge, $180
Booties are my favorite type of shoe. In fact, I recommend them to nearly all my clients. You can see my predilection for booties over on my client portfolio. They dress up a look like a high heel does, without sacrificing any comfort. For these, I love the offerings from Rag & Bone, Ecco, and Paul Green.
Rag & Bone Margot Booties, $495
Ecco Shape 35 Booties, $180
Paul Green Water Resistant Booties, $389
My Top 3 Shoe Shopping Tips
One of the best ways to get maximum life out of your wardrobe is to choose versatile pieces that can be worn for different occasions. A versatile dress can easily go from desk to dinner. A dress that can comfortably be worn at work, out for drinks, and to a wedding will need to be somewhat basic in nature. Basic doesn't have to be boring. For the dress itself, you'll want more of a "blank canvas". When creating multiple looks from the same dress, you change the formality by switching out your shoes and accessories. For example, a red sheath dress can be paired with black pumps and a grey cardigan for work, or paired with metallic sandals and gold jewelry for a wedding. Now we'll get into how to tell if a dress is actually versatile when you're shopping.
For fabrics, you'll want a comfortable, breathable fabric that can be dressed up or down. Rayon, stretch cotton, silk, and jersey tend to be the stuff versatile dresses are made of. You want to avoid fabric that is too formal (think lace, sequins, tulle), fabric that reads corporate (think grey flannel), or anything extremely casual (like denim or hemp). In the example below, the Eileen Fisher dress on the left is a hemp cotton blend that is far too casual to be considered versatile. It's really a roomy t-shirt masquerading as a dress. I'm sure it's fabulously comfortable and flattering on most, but it would not be appropriate for a wedding guest. On the left, this silky number by A.L.C. could easily be worn to a wedding or a board meeting, by switching out shoes and jewelry.
While trendy details can be fun for your special occasion pieces, these are best avoided when shopping for workhorse garments. Avoid shoulder cut-outs, flared sleeves, visible zippers and anything else that might limit your layering options. You'll also want to skip over evening embellishments like sequins and rhinestones. While these features can be beautiful, a truly versatile garment won't have them. I must admit that the dress on the left is fantastic, however, the cutouts and the flared sleeves mean you can't change up the look with various cardigans or jackets. Also, if you're in San Diego, like me, or any more casual city, this might be a little too much look for your average workday. The Eliza J dress on the right has simpler lines and gives you many more options when it comes to layering pieces.
Go for a sleeveless, short, or 3/4 sleeve lengths. This way, you can easily layer a jacket, cardigan, blazer, shawl, or even another top over your dress. Bell sleeves, long sleeves, or statement sleeves severely limit your options. As mentioned above, I would also avoid dresses with shoulder cut outs if you're seeking versatility. While they're certainly "of the moment" trendy, they are not appropriate for more conservative workplaces and I suspect they will look dated rather quickly. With the Eliza J Dress on the left, the sleeves again would limit layering options. The Dorothy Perkins dress on the right has more potential. I also wanted point out that a versatile dress doesn't have to be a solid color. It can have pattern and texture, as long as you have other things in your wardrobe that pair well with it.
No matter how versatile a dress is, if you need new shoes, a new jacket, and new jewelry, to go with it, it's not the dress for you. Try finding something that works with the other items already in your wardrobe, unless you're ready for a complete closet overhaul. If that's the case, you may want to enlist my help.
Shop Versatile Dresses
Below you'll find a few more of my favorite versatile dresses.
City Chic Fit & Flare Dress (Plus), $119
Ted Baker Printed Sheath, $198
Tahari A-Line Dress, $128
Ann Taylor Belted Dress, $129
Karen Millen Pleat Detail Dress, $199
I'm Jaquelyn Wahidi. I'm a personal fashion stylist, writer, and entrepreneur in San Diego. I help women organize their closets, define their style, and shop with intention. My style blog features practical fashion advice for women everywhere. Addicted to blazers since 2004.