What I Wear | Play In Heels

If you follow my Instagram (@Mack10988), you know all too well that I never feel fully dressed without a hat. Today I’m topping off my looks with Grace… Grace Hats, that is. Grace has such a variety of styles from cozy casual to quirky fun to feminine chic. There is a hat for everyone, even if you are new to the hat scene. I have four hats to show you that I simply can’t stop wearing.

First off, let’s talk about this Fulling Beret. What is not to like? It’s an effortless way to add a little français in your day. And can we say no more bad hair days? This hat is cute enough to keep on indoors as part of your ensemble.

Sure, it’s pretty cute, but let’s get down to the nitty gritty, because it’s always about the details. I love that this hat is warm enough to replace some of my “function over fashion” winter hats. I wouldn’t go on an arctic dog sledding adventure in it, but for the average winter day, this hat keeps me covered. Plus, I don’t have to worry about taking it off once I arrive at my indoor destination where I would normally make a run to the nearest bathroom and try my best to salvage some sort of presentable hairstyle.

Not all berets are created equal. Perhaps you are a fan of the floppy berets that have a mind of their own and flop wherever they will. I prefer berets with a little more structure to them. Call me a control freak, but I want to be in charge of when and where my beret flops. So I love that this beret has enough weight to it to retain its shape and “behave.”

|hat: courtesy of Grace Hats (you can get one here)| |coat: Zara| |sweater: J.Crew via Poshmark| |jeans: Express| |boots: Sam Edelman (ON SALE)| |clutch: kate spade (sold out but this one is available on ebay)| |gloves: Coach|

If you’re a fan of throwing on a baseball cap, and you like a little fun and whimsy in your life, you are the perfect candidate for this next hat, which has become one of my favorites to throw on when I need a little something to spice up a casual look.

The trend undoubtably began before J. Crew got a hold of it, but thanks to the stylists behind the company, baseball caps have branched out from the strictly casual. Once the mainstream company began showing models in baseball caps paired with not-so-casual attire, the baseball hat started getting makeovers.

I love how this Palette Cap is as easy to wear as a baseball hat, but has so much more to offer in terms of style. Fur (whether faux or real) is a big hit this year, and this cap is perfectly on trend.

Many of the Grace hats are adjustable, which is a must for me because my head gets swamped by the one-size-fits-most hats. Unlike a traditional ball hat, the adjustable strap is cleverly hidden inside the hat and is super easy to tighten or loosen as needed.

|hat: Grace Hats via Brim (you can get one here)| |coat: Zara| |shirt: Madewell| |jeans: Express| |boots: Sam Edelman (ON SALE)| |bag: Rebecca Minkoff (ON SALE)| |sunglasses: Karen Walker|

This next hat is not for the timid. It’s a statement piece and, just like anything else with the word “statement” in front of it, a good conversation starter. Maybe not intended for the beginning hat wearer, but I just can’t help smiling when I wear this one.

In case you were wondering, yes, the googles do come off. So if you are feeling really adventurous you can wear them. I love this cute and unique alternative to a plain black hat. It is such a fun piece to have and play around with different looks.

And what better place to showcase this Aviator Hat than in the Birthplace of Aviation, home of the Wright Brothers, and my own hometown, Dayton, Ohio.

We’ve come a long way since that first flight, but this hat harkens back to the days of Amelia Earhart and fighter jet pilots whose goggles were not a fashion accessory.

|hat: courtesy of Grace Hats (you can get one here)| |coat: Michael by Michael Kors| |jeans: Express| |boots: Sam Edelman (ON SALE)| |bag: Rebecca Minkoff|

Speaking of nostalgia, this next and final hat has all the old school glam of Old Hollywood. This hat can be worn with hair up, making it more dressy, or hair down.

This Caplet is perfectly on trend with its fur. And like the Fulling Beret, it’s effortlessly chic and easy to wear. This hat can take you from day to night with no hair touch ups needed.

Again, like the Fulling Beret, the Caplet is a hat that will go from outside to inside with no need to take it off. And it looks just as good with a turtle neck and jeans as it does with a dress. It is one of those hats that I like to call an instant chic maker.

|hat: courtesy of Grace Hats (you can get one here)| |coat: J.Crew (not current)| |boots: Sam Edelman (ON SALE)| |bag: Rebecca Minkoff| |gloves: Forté| |sunglasses: Karen Walker|

You can find Grace Hats here, here, here, and here.

*This is a collaboration with Grace Hats. All thoughts, pictures, and opinions are that of Play In Heels.

Packing for a trip can be a daunting task, especially with today’s flying restrictions and regulations. When I began packing for my recent trip to San Francisco my main concerns were, “What am I going to pack to keep me comfortable enough for day time sightseeing, yet trendy enough for night time fun? And how will I keep my bag under the 50 lbs weight limit and still feel fashionably dressed everyday?” This task became more cumbersome as I looked at the fickle San Fran forecast. Although November is typically in the 60s (a welcome change from the 30 degree days we were having in the Midwest), what the temperature actually feels like can vary with the changes in wind, sunshine, and the onset of fog (which is so common it’s referred to by first name…Karl, who you can follow on Instagram under the name @karlthefog).

The key to successful packing for a trendy city? Taking pieces that can transition from day to night with a few simple changes and additions. And one word…Layers. Layering allows for various looks and outfit changes without overpacking. You can utilize the same pieces but achieve completely different looks.

So if you’re going to San Francisco, feel free to wear flowers in your hair, but I would suggest a versatile leather jacket and a wool/felt hat… to start.

Attending PoshFest, a fashion conference for the Poshmark app, was my first stop in the Golden Gate City. Located in the San Francisco Design Center, I needed to be on trend, but comfortable enough for an all day conference. Because I wasn’t doing a lot of walking on those treacherous, infamous San Fran hills, and because I love them and pretty much wear them everyday, I chose to wear heels on this, and only this, day. I opted for a black mini skirt contrasted by an oversized white t-shirt. I paired fun polka dot tights and knee-high socks to keep my look daytime appropriate. I topped my look off with a black leather jacket and a metallic bag. The bag kept my look out of the all-black zone.

My next stop was Fisherman’s Wharf for some typical tourist sights. With views of the Golden Gate Bridge, Alcatraz, the Bay Bridge, and sea lions on Pier 39, I shamelessly played tourist. For a long day of sightseeing, I needed to make sure I was comfortable for lots of walking and weather changes from morning to afternoon. I chose white cutoff shorts to get that Cali vibe, but paired them with boots to keep the look fall appropriate. A sweater and utility jacket kept me warm, but not too warm for when the sun came out. I topped my look off with a black fedora, again keeping my look fall appropriate.

What would a trip to San Francisco be without tasting wines made just an hour away in Napa?

Day three was reserved for some upscale shopping (well, more like window shopping) in Union Square. Being a midwest gal, I wasn’t prepared to see palm trees alongside Christmas trees and ice skaters on a 60 plus degree day. Half Rockefeller Center, half California cool, but definitely a sight to see. With everything from Prada, Chanel, and Valentino to big department stores like Saks, Macy’s, and Bloomingdale’s, I had my work cut out for me. Luckily I found an app that showed all of the stores and listed them in order by proximity to your current location. This helped out my legs and feet by keeping me from backtracking. Comfort was the name of the game, but there was no way I was going to walk into Chanel looking “comfortable.” I went back to a black mini skirt paired with tights, but I opted for flat black boots this time around. I chose an olive colored blouse and topped it off with the viral trending fur vest. I was comfortable enough for a day of shopping, but felt trendy enough to walk into any store.

The “heart” of Union Square complete with palm trees, a giant Christmas tree, and ice skating, yes, ice skating.

Doing a little shopping. What do you think? This luscious (faux) fur came home with me to assist on those chilly days ahead.

After doing some damage at Zara, next stop was some luxury indulgence…if only for the eyes (sigh).

As night time rolled around, I didn’t have to change much to go from day to night. As the sun went down and the night got chillier, I switched out my blouse for a slightly slouchy sweater, utilizing what I have deemed “the messy tuck.” I lost the knee high socks and switched out my tights for a pair with less whimsy and more sophistication.

As you can see, this gorilla is highly impressed with my day to night switch-up.

I couldn’t go all the way to San Francisco without seeing the city I fell in love with as a child of the 90s. So it was off to Pacific Heights to see the quintessential San Francisco neighborhood we know and love from movies and TV shows. First stop for me, the Mrs. Doubtfire House on 2640 Steiner (which, by the way, was the address given to Mrs. Doubtfire over the phone in lieu of a fake “movie” address).

This neighborhood offers fantastic views of the bay, romantic victorian style houses, and those infamous San Francisco hills. It all comes with a hefty price tag, of course. Most of these homes are multi-million dollar houses.

This was one of the chillier days (if you can call 60 degrees chilly). So I went with a light weight coat that I scored at Zara while in Union Square. I kept it casual, yet cool with a (here it is again…) “messy tucked” chambray shirt. I topped everything off with a fun and playful hat.

No trip to San Francisco would be complete without an overpriced ride on the Trolley, or Cable Car as it is known there.

There are so many cool and unique neighborhoods to see in the San Francisco area. But I only had so many days and and a limited number of hours to enjoy this thriving city. So my last stop was North Beach. Full of Italian cafés and some must-stop shops like the Goorin Brothers flagship store, whose first-rate sales associates not only custom fit a hat for me, but also spruced up the one I was wearing (from a different company even!) that had gotten full of lint from traveling.

For my literature lovers out there, North Beach is also home of the Beatniks. Amidst the tall skyscrapers and iconic Transamerican Pyramid hide book stores, like City Lights, dedicated to the beatnik generation. You have to keep your eyes peeled, but literature junkies will find themselves at home in hidden gems like Jack Kerouac alley.

The Jack Kerouac lover in me was inspired to come out in the form of a slightly grunge, white t-shirt and leather look. I took the opportunity to wear my newly found Goorin Brothers hat (I couldn’t leave San Francisco without another addition to my hat collection).

The black skirt and the messy tuck came out to play again, but some simple changes in hairstyle and the addition of the hat switched up my look.

Some people bring home magnets. Some people opt for keychains. Others go for coffee mugs, snow globes, or t-shirts. I collect MLB baseball caps. If I go to a city that has a Major League Baseball team, I bring back a baseball hat as a souvenir. I know, hard to imagine me collecting hats! Eh-hem. Anyway, I obviously couldn’t leave San Francisco without a Giants’ ball hat, especially after their big World Series win just weeks ago.

So I enjoyed one last San Francisco eat at SFO,