What Shoes To Wear With Your Straw Hats & More

Hats have been making a slow resurgence over the past several years, much to my delight. I am a big aficianado of the lovely ladylikeness or saucy jauntiness of a hat, as well as its practicality (goodbye facial moles!) and ability to complete an outfit. There’s something so cool, so nonchalant and yet so look-at-me about a hat. I expect that as more and more people start to wear them, it won’t be so noticeable anymore to wear one. They will become a much more mainstream accessory, hopefully, and will be paired well with shoes.

Jennifer Aniston was recently photographed carrying a straw hat, Beyonce and Rihanna love to wear them, and many a celebrity from Sienna Miller to Leonardo DiCaprio is frequently seen enjoying the cool Havana ease of a straw hat. Most of the ladies sport the look with shorts or a shortsuit/onesie type outfit. But the question is, what kind of shoes do you wear with them?

The lovely Jennifer Aniston goes for neutral Weitzman wedges, a perfect answer, in my opinion. (Aside: I love Jennifer Aniston more and more as the years go by. She annoyed me on “Friends,” of course, but she is great now. I think that she is an inspiration to a world that tells you that the sexiness of a woman dies at 40. Yes, she has the body of a 20-year-old, but it’s more the way she carries herself. She’s so much more confident now, and it shows. It’s all I can do to hold back a “You go, girl! Who needs Brad Pitt when you’re cougaring every hottie in sight and doing better movies every day and running your own production company?”)

Be, never the tame one, pairs yellow spikes that have been surmised to be YSL (since we all know she hardly ever lets anything non-top notch designer touch her body) with her yellow hat.

Riri, resplendent in white and a printed patterned onesie short, goes for casual bejeweled sandals.

Cindy Crawford, still one of the sexiest ladies around, in my opinion, even more so for how well she’s aged, prefers a more cowboy style hat, at least for this ad. I think the cowboy style is a “Proceed With Caution.” If you are down South, or if you are on vacation, or at the beach, I think it is fine. Otherwise, I wouldn’t be caught dead in one, especially in New York. It nettles me that western style cowboy boots are in, AGAIN, this fall, when I have had to endure so many Williamsburg and downtown New York girls wearing them. It’s pretentious, in a word, to sport cowboy style when you are so obviously metropolitan.

This summer in New York, St. Marks, the street that is the arbiter of plebeian downtown New York fashion, where vendors hawk mainstream downtown fashion to NYU students and broke 20-somethings and 30-somethings, is loaded with straw hats right now. Go there for your bargain hats.

Here are a couple hats I bought on St. Marks.

This first smaller hat I bargained down to $11. (Pretend to walk away and you will get a much better deal).

This second hat was $18 (I bargained them down from $25).

The second hat curves nicely into a floppy brim when worn.

But what kind of outfits and shoes have I been wearing with these hats?

For the smaller hat: mostly a t-shirt, miniskirt and sandals or a big men’s shirt half unbuttoned with the cuffs rolled up, plimsolls or Keds and shorts.

For the larger hat: beachwear, a long buttoned loose white shirtdress with billowy sleeves, or a classic summer sundress in white, with wedges or cone stacked heels in soft gold or neutral colors. Do it up like this with simple black sandals for a more formal event.

For a dramatic floppy hat, you can do more with the other accessories than you can with a small hat. Work it on out with some shades, some artsy fartsy “ethnic” earrings and a white top like the sexy bohemian lady of our times, Kate Hudson.

For shoes, a great option would be straw-effect sandals as well, like these by milliner and shoe designer Eric Javits. I’m not a big fan of straw shoes, but man, do his look good!

Here are some of his lovely hats. I especially like the striped one on the right.

Here is Britney in one of Eric Javits’ hats. I bet you she’s wearing sandals, probably white and maybe with straw or bejeweled accents.

You want it to look like this with a straw hat. Effortless yet so chic. The shoes are a perfect match for the dress and hat, carrying the theme of yellow in the straw, black in the band of the hat and the base of the shoe. Gorgeous.