A Personal Item Packing List for Five Days in San Francisco

It’s time again to share one of my favorite kinds of posts: a packing list post!

If you’ve read my San Francisco guide or my Nisolo boot review posts, you know that I traveled for work with just my under-the-airplane-seat bag (and even if you didn’t read those posts, I guess you know now too—but you should still go read them!).

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Any time I travel, I try to maximize style and comfort, while minimizing the amount of stuff I bring with me. I generally accomplish this by relying on monochrome dressing, creative layering, small accessories, thin baselayers, and re-wearing garments—and this time was no different.

The biggest challenge for this packing list was the weather, as cold-weather garments take up more room than warm-weather ones, however, cooler weather has a bright side as it allows for more mixing-and-matching fun!

Looking for more packing list inspiration? Discover what's in my suitcase each season: Spring | Summer | Fall | Winter

A few key strategies for this trip: packing just one set of ultra-thin pajamas, wearing a very comfortable bra on the plane, layering over and under my dresses for a different look, and relying on just one coat and one pair of boots the whole time. Oh, and since I’d be working in a jewelry booth at West Coast Craft, I left my own jewelry and scarves at home.

Is this packing list the epitome of current trends? No, not at all. Do all of these outfits feel timeless and put-together? Yes, I certainly think so. Take a look at the full list of items I brought (well, minus undies and socks) and a few of the outfits, and share your thoughts!:

SAN FRANCISCO PACKING LIST

Collage image of all pieces packed for five days in San Francisco — Tops | Cropped Turtleneck* | Cashmere Turtleneck* || Dresses | Sheath Dress* | Ruffle Dress* || Bottoms | Denim Skirt* | Ponte Pant℅ [take 20% off your first order with code WAYWARD; reviewed here] || Outerwear | Wool Coat || Pajamas | PJ Tee* | Lounge Bra | PJ Pants || Shoes | Chelsea Boots℅ (reviewed here) || Accessories | Black Tights | Face Masks | Belt* | Beret* | Crossbody Bag* | Sunglasses℅ (reviewed here) | Digital Camera

SAN FRANCISCO OUTFITS

Two images. Image one: Alyssa in a large mirror with her suitcase at the airport. She is wearing a black dress with ruffles at the shoulders, black pants, and black boots. And a face mask. Image two: Alyssa in a shop, she is wearing a black turtleneck, black denim skirt, black belt, black tights, grey coat, and a grey beret — || *Left* | Ruffle Dress* | Pants℅ | Face Mask | Coat | Boots [save 20% with code WAYWARD20] | Carry-On | Travel Bag || *Right* | Sweater* | Denim Skirt* | Tights | Coat | Belt* | Bag* | Face Mask | Beret* ||

Alyssa standing in a very green field. She is wearing all black and a grey beret — || Sheath Dress* | Sweater* (over dress) | Tights | Coat | Boots℅ [save 20% with code WAYWARD20] | Sunglasses℅ | Beret* | Bag* ||

Two images. Image one: Alyssa sitting on a concrete wall in front of the golden gate bridge, wearing a grey sweater, black pants, black boots, and a charcoal coat. Image two: Alyssa standing on a street sidewalk wearing all black — || *Left* | Cashmere Turtleneck* | Ponte Pant℅ | Boots℅ | Coat || *Right* | Ruffle Dress* | Tights | Coat | Boots℅ | Bag* ||

*many items in my wardrobe are thrifted and/or several years old, and no longer available from the retailer; links provided are for suitable substitutes. If you're looking for the exact item, leave a comment and I'll try to help you locate the piece secondhand!

FINAL THOUGHTS ON PACKING FOR FIVE DAYS IN A PERSONAL ITEM

This is just the moodiest packing list, isn’t it?

By the end of the trip, I was craving a little more color than black (no shade to charcoal, but it’s just not quite different enough), but I also recognize it was what I needed to bring to be able to pack practically and fit in behind the booth. Working through body changes has left me with a smaller closet, but I’m still thrilled I can pack cohesively all the same.

Would I have liked a larger bag? Of course! But I feel confident knowing I can pack for so long in such a small space—even when it’s chilly.

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Questions for you

What are your favorite tips for maximizing your fall/winter wardrobe pieces?

What is the longest trip you’ve taken with a personal item?

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Traveling Light: Packing List for Five Days in San Francisco