Even though I would never let my attire hinder having an extraordinary travel experience, for me proper planning does include a Google search for the latest fashion trends of wherever I am going to visit. Mostly, to avoid having “Tourist” stamped across my forehead. As if having a camera hanging around my neck wasn’t a convincing enough sign. Deciding what to wear in London was a process that mostly focused on hunting for the cute and comfortable travel boots. But, what I should have been focusing on was skirts, stockings and skinnys.
London is full of extremely well-dressed folks wearing proper blue suits, mid-thigh skirts, skinny pants and stockings in a variety of colors.
I rarely see women wearing stockings in my Northern California hometown and I have not owned a pair since the 90s. We are very casual in Sonoma County; jeans and a blouse is evening attire. This wouldn’t have been proper for what to wear in London.
Londoners are pretty dapper dressers.
What to Wear in London (& What I Wore)

Most ladies donned the simplest black stockings, but several others got creative with color and pattern.
Boots were all the rage, just not the knee-high ones that I had painstakingly purchased. Anything mid-calf or lower was fashionable, in particular ankle boots.
Note to self: Get a pair of ankle boots before heading back to London.
Skinny jeans, which are a fantastic boot companion, were scattered throughout the streets. Mostly on men. And they came in an assortment of shades, the least popular being the standard blue jean.
Suits & Ties: The pubs, London underground and shops were filled with them. That is something I could get used to. Easily.

When I packed my suitcase, I did some things right…and some things wrong.
The Good: Not only did my large crossbody bag fit my DSLR camera, maps and guidebooks, but it was also in style. Another good is that I only brought skinny jeans.
The Bad: The puffy jacket was so “hot” in Italy two years ago, not so much in London today. My knee-high Leslie Sharon boots gave me miles of comfort, but not a place on the cities best dressed list.

Do you research fashion trends before traveling? Do you go for comfort or style when traveling?
Traveling Soon? Use my Favorite Resources for Booking Your Trip!
Book Your Flight
Skyscanner is my favorite flight search engine, because it checks dozens of airlines so you can easily find the best fare deals. You can also select ‘cheapest month’ to find the lowest fares for your destination (I use this all the time!).
Book Your Accommodations
I use both Booking.com and Expedia for hotels, because each offers a couple different hotel choices and I like to compare the reviews on each one. If you have a group or are looking for more of a home atmosphere, head over to VRBO or AirBNB that has houses, apartments and even just a room for rent in every price range.
Book Your Rental Car
If love the freedom to explore like I do, driving from place to place is the best option! I always book with Discover Cars for the best prices and top brand options.
Book Some Fun Tours!
Viator and Get Your Guide are my go-to search engines for cool bucket list experiences! Each one can have different tours, so check both—why limit yourself, right?
Don’t Forget Travel Insurance
Travel can be unpredictable. Whether it’s a last-minute cancellation, an injury, or (ugh) theft, things happen. That’s why I recommend never leaving the country without travel insurance. Here are my faves: Safety Wing and World Nomads.
Get Packing & Travel Essentials Ready
Check out the Bucket List Journey Amazon Store to find all my favorite travel essentials. Everything from Packing cubes, to travel adapters and toiletry containers to walking shoes.
*Lastly, check travel.state.gov for visa requirements and safety information.
You Might Also Enjoy
Walk Across London’s Abbey Road and Stand in a Red Phone Booth
Attend a Proper British Afternoon Tea in London
A Guide to Changing of the Guard at London’s Buckingham Palace
12 Tips for Navigating the London Underground
Take a Spin on the London Eye
Stroll Through London’s Hyde Park
Learn Sign Language While Drinking at the Oldest Wine Bar in London
Aww I loved London! I was studying abroad and had actually packed sensibly…not fashionably… d'oh! So I felt rather out of place in London. Sadly, I had to go home two weeks in for a death in the family, and when I returned to my studies abroad I decided to bring some more clothes over. A trench coat is a must, as are skinny jeans and boots!
I was trying to decide between bringing a trench coat or a puffy jacket. But, I opted for the less trendy puffy jacket because it was the warmer of the two!
You still look adorable trendy or not. I never look up trends when I travel, maybe its because I just roll and shove my clothes into a backpack, and just hope they will dry before my train leaves the next day after washing them in the sink. In China I think I wore the same two things for pretty much the entire trip, at least that's what it looks like in my photos. I do bring a straightener though! I can't live without that.
I absolutely bring a hair straightener too!
Totally agree with you on the short boots in London. We were in London for a day, then took the fast train to Paris for two days, and then down to St. Raphael in the French Riviera. My daughter and I couldn’t believe all the short, black boots the women were wearing. Mainly Dr. Marten’s or similar. So cute!!! London was rainy and windy.
Everyone in Paris was wearing white sneakers!!!! It was warmer there. Then when we got to the French Riviera everyone dressed casual except when we were in Monaco!!!
It was a challenge to bring clothes for the three places and different climates!!!
Well, you look cute even with the puffy coat! lol. When I was working in London a fellow Canadian co-worker showed up on Casual Friday in July not wearing stockings. A British colleague pulled me aside and was like, "Do people not wear stockings in Canada?!" Haha. She was horrified. I had to give my co-worker this awkward "you have to wear stockings here even in summer" talk.
LOL! I actually just thought it was just a fashion statement, not a requirement!