Karen Walker Sunglasses | 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,

Grabbed a beer,

And headed home to 28 degrees.

Trying to cash in on the crop top trend but don’t want to look like a sixteen year old stuck in 1994? To keep your 2014 look from slipping back in time to Britney’s “Hit Me Baby One More Time” era, pair your crop with sophisticated, longer pieces on the bottom to look polished, chic, and still perfectly on trend. Below you will find one crop top worn three ways, from modest to slightly edgy, all while remaining chic and polished enough for date night downtown.

Wear a crop top over a dress to get the appearance of wearing a crop top with a skirt, but without the risk of showing any midriff. This will keep you looking appropriate in even the most modest of places, while still keeping you on trend.

Pair a crop top with a high waisted midi skirt and you won’t feel like you’re bearing all your mama gave you.

Wear a skirt with lots of volume to counteract wearing a tiny top. Choosing a high-waisted style will keep you looking chic even with a peek-a-boo middle.