If your feet can only handle comfortable shoes, take comfort (no pun intended) in the fact that you are not alone.  In fact, you are in the majority.  This certainly isn’t the first post I have written about comfortable shoes and comfort brands who make stylish styles you would actually want to be caught dead in (all which you can read here, here and here).   But in today’s post, I want to talk about how to be stylish when wearing comfortable shoe styles, as there seems to be this weird disconnect.  Just because you can’t teeter around in 4″ stilettos or run a marathon in platforms it doesn’t mean that mean you have to dress like a dud.

Go to any department store website or a site like Zappos.com and search comfort styles and you’ll see there is a treasure trove of attractive shoe styles with comfort in mind.  Long gone are the days of Frankenstein shoes, block heels and garish square toes that could easily fit a swollen foot that has been hit with a hammer and bandage wrapped.  So, really, there are no excuses any longer for looking bad in your shoes.   Why is it that when a woman thinks her shoe choices are relegated to comfortable ones that she can’t be stylish?  Below are five shoes, all from comfort brands, that are part of some pretty stylish looks, if I do say so myself.

How to Look Stylish in Comfortable Shoes

comfortable shoes

If you need to wear flat shoes look for styles with some support.  Truth is, a small heel is better than a pair of shoes that are totally flat.  Plantar fasciitis often comes from wearing flat shoes because the Achilles tendon gets overly stretched, which causes that pain on the bottom of the heels.  If you have ever had it, it’s terribly painful, as is the cortisone shot that can be administered to ease the pain.

In this outfit, I started with these orange flats.  Not only are they super cute but they are also from Dansko, a company that couldn’t make a pair of uncomfortable shoes if they tried.  The rest of the outfit is super stylish with a pair of white jeans from J. Crew, a printed tunic from Anthropologie, a pair of emerald chandelier earrings from Max & Chloe, navy Tory Burch bag and Banana Republic gold bangle.

Outfit #2

comfortable shoes

There is no way you can’t be stylish with such a trendy pair of heeled oxfords, like these from Earth, especially when styled with these boyfriend jeans from the Gap, this camel cardigan over a short sleeve button down from Brooks Brothers and long green necklace from Bauble Bar.  The outfit is weekend ready and finished with this caramel bag from Liebeskind.

Outfit #3

comfortable shoes

Does your life sentence of comfortable shoes have you believing you can’t be sleek and modern in your looks?  In this outfit I am using these leopard Gabriella Rocha mary janes to prove otherwise.  The shoes have the perfect heel height and a supportive strap across the instep.  Here they are styled with a pair of black cropped pants, a white Reiss tunic, biker jacket from French Connection, camel scarf, black handbag from Nine West and gold drops from Bauble Bar.  Nobody is going to assume you have foot problems in this outfit.  Trust me.

Outfit #4

comfortable shoes

If you can wear heels, choose styles from known comfort brands, like this pair of shooties from Bella Vita.  Worn with pants or jeans or even with a skirt, like it is styled here with this zipper pencil style in blue from J. Crew, shoes like this are perfect for work.  The tan shade creates a longer leg line and the small platform acts like a shock absorber when the balls of the feet hit the ground.  Many women shy away from platforms, however, a small one (like 1/2″-3/4″) is actually quite comfortable.  Plus, this extra platform height allows you to wear higher heels without as much discomfort.  Added to this outfit is a blue wrap knit top from Modcloth, a stunning agate bib necklace by Janna Conner and a cognac purse.

Outfit #5

comfortable shoes

Talk about trendy, culottes, like this pair from Reiss, have been making their way back on the scene for some time now.   To not look squat, or like your legs have been chopped shorter, wearing them with beige or skin tone shoes is the way to go.  For comfort, I used these shoes from Aerosoles, and styled the outfit with a white top from Alice + Olivia, a bib necklace from Bauble Bar, stacked bracelets from Macy’s and, for an expensive finish, this red Valentino bag.  See, you can combine Valentino with comfort.