First rain! WIW and perfect boot length question

I'm so excited that it's the first real rain of the year here in SF. Of course, it imposes some constraints on our clothing, but it was also a chance to break out my favorite fedora! My boyfriend got it for me at Rag & Bone a few years ago but I rarely feel bold enough to wear it. Rain is the perfect excuse.

Too bad my hair is dripping wet in these photos; the hat looks much better with my hair dry and curly like it is now, but I was in a rush to get out the door and I never blow-dry it.

Also, my lovely Madewell tall boots seem to be entirely wrong on my legs. I snatched them up when they somehow rang up at $70 instead of $300, but they are certainly too tall and big around the top for my legs. The last photo shows one boot and one bare leg for comparison. The question is, should I keep them to wear over jeans, should I have my excellent cobbler shorten them, or should I sell them and buy slightly shorter, zippered boots instead?

I finally found the right place for photos: inside my roommate's empty closet! It has a mirror and the only south-facing window in the house.

This post is also published in the youlookfab forum. You can read and reply to it in either place. All replies will appear in both places.


  • minimalist replied 4 years ago

    Love the fedora!

    The boots aren't horrible. That gap size (skirt hem to boot) is a tough one to pull off, and I'm seeing a lot just like it today. Shortening is one option, but if you love them over jeans, maybe look for other skirt-able boots?

    The rain has a smile on my face, and I'm suddenly willing to compromise a bit on my coat search.

  • Suz replied 4 years ago

    You look adorable in that fedora. 

    As for the boots, I am not sure. Do they have a zipper? Can they be made snugger at the calf? Maybe snap some pics with jeans so we can see how big the gap is. Before YLF I had no idea how boots were supposed to fit or I felt lucky to get any that halfway fit at all. Now my standards are higher and it's harder than ever to find the darn things. 

    And wait...that is INSIDE your roommate's closet? Whoa...some closet....

  • deb replied 4 years ago

    Love that hat and you look great in it.

  • Greyscale replied 4 years ago

    Suz, the first photo is the bedroom and the others are the closet (black and white floor). The closet isn't so big, but it's entirely empty since he's only a part-time resident. I am questioning my decision to take the other bedroom with no closet (and buy a wardrobe) though!

  • RunswithDolphins replied 4 years ago

    You are owning that fedora!  It looks awesome with your hair.  I love your outfit and agree the boots just seem a bit too big on your legs with tights. They look like great boots and might be just right over jeans or skinnies.

  • Gail replied 4 years ago

    The boots were a steal at $70. I would imagine that they would be fine with jeans tucked in. Perhaps purchase a more form fitting pair to wear with skirts and dresses. I have extremely skinny calves and have a lot of trouble getting boots to look decent. I have a really old pair of BCBG boots that I had my shoemaker take in on the back seam for me. They fit  well now.
     I just purchased a pair of Via Spiga Carly black riding boots at Marshalls that fit my legs. Actually the left one is better than the right ! I have to wonder if it is my uneven legs or the boots are slightly different. 
    What should the gap size be between hem and top of boots ?

  • Marmee replied 4 years ago

    Who has an empty closet??  Perhaps you could sublet!  YLF!

    Is there a gap in the boots when you wear them over jeans?  If so, I'd consider selling them if the cobbler can't shorten them and make them a bit snugger.  

  • Greyscale replied 4 years ago

    I often find that the right shoe is looser than the left, at first, because people usually try on the right shoe in the store. Maybe especially true for me because my 6.5 is usually the floor model.

  • Greyscale replied 4 years ago

    Marmee, the closet thing is a funny story. The rental market here in SF is nuts. And my best friend just bought a house down near his office (Google) but misses city life. So, my boyfriend and I justified the cost of a nice spacious apartment by renting out the 2nd bedroom to my best friend and his wife as a pied-a-terre. They're here once or twice a week. We all just moved in, and I'm waiting to see if we can store anything in their room or if that would be unfair since they're paying for it.

    My cobbler will shorten them but says he can't take the seam in. But shortening them is probably enough - I don't have very narrow legs, it's just that the boots hit above the full part of my calf and look very wide as a result.

  • replied 4 years ago

    Great fedora. I like the boots, I think they would be snugged over jeans. With tights/leggings I think a scrunchy pair of boot socks is what most people do to provide texture and fill for the gap.

  • Greyscale replied 4 years ago

    Just because it was bugging me, here's an update with dry hair (and wet hat!). I think the hat looks better with more volume under it. Maybe I should start blowdrying my hair? I never have (hate spending time on that type of thing) but it takes hours to dry on its own.

  • minimalist replied 4 years ago

    I like the hat both ways. If you do start blow-drying, a good dryer makes the process less gruesome. (What am I saying?! I have a good dryer but still avoid it whenever possible.)

    Gail, I don't buy "shoulds" for gap size. (Ask Angie, though.) It's more about finding flattering hem length *and* flattering boot height *and* harmonious overall outfit proportions. Yesterday I was seeing a lot of just-above-knee skirts paired with just-below-knee boots, leaving a hand-breadth of bare skin. Not many people's knees can stand up to becoming an unintentional focal point that way. My best hem length is just below my knee-cap, and boot height, well, I'm trying to figure that out.

  • Aleta replied 4 years ago

    I love your outfit in #1, is that a knit dress? It all looks great, you can definitely wear a hat well. To me the boots do not seem too tall, just right, however they do look a little too wide, if they were taken in a bit they would be perfect. Congratulations on scoring such a bargain.

  • Scarlet replied 4 years ago

    That is a great hat. The boots seem just too wide. I would be inclined to sell them and look for something else for your fab legs.

  • Zapotee replied 4 years ago

    Buaha, love pic #1. That jacket is amazing. You look great, no sickie face at all.

  • Greyscale replied 4 years ago

    The dress is a knit wool dress from Cotélac (usually out of my price range but they had a sale). I like it because it's a little more refined than some sweater dresses but still easy to wear. It has slightly puffed shoulders that originally had shoulder pads - but with my strong wide shoulders, the shoulder pads just looked silly, so I took them out. I want to find smaller pads to keep the sleeves puffed correctly, though.

    Zapotee, wondering if that comment was meant for Rae's sickey-face post? :)

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