Petite Fashion Challenge #11 – An Outfit Made for Sightseeing

Burberry trench (altered), size 2 (similar) :: Theory blazer, size 00 :: LOFT dress shirt, size 00P (altered) :: H&M t-shirt, size 2 :: Paige jeans, size 24 (hemmed) :: Missoni scarf (similar) :: Coach shoes, size 5 :: Helen Kaminski Handbag (similar)

This month’s Petite Fashion Challenge, hosted over at Ski Petite, is:

Put together an outfit made for sightseeing. It should be one that will be comfortable for walking around in and can last you from the early morning until dinner and drinks in the evening. Plus, you’re on vacation, so you’d better make sure you look good in photos, which you’ll have for years to come.

And…a sightseeing I did go! To Chicago!

I spent a few days last week in the beautiful city of Chicago, so I was faced with the eternal question…what do I wear?! As a Southern California girl, I was a bit worried. I was expecting the weather to be cold, but I’m without much experience of just exactly what “cold” means. And coming from a city with such a big car culture, I was worried if my feet would hold up for several days of walking the city.

I learned two things…I can layer a surprising amount of clothing under my trench coat…and no, my feet will not hold up for several days of serious city walking.


I was itching to wear a pair of heels the entire trip, because I just don’t feel put together in a pair of flats. The flats beat up my feet by the end of the trip…but a pair of heels would have murdered them. Other sight seeing necessities included a big bag for DSLR schlepping and a fun, colorful scarf for style. When we went out for dinner, I simply removed the trench coat to reveal my blazer and dress shirt combo.

Curly haired readers – what on earth do you do when you travel? I have been known to schlep a blow dryer and diffuser around in dire situations, but that’s just not practical. I also prefer to use mousse for my hair, which doesn’t come in carry-on 3oz. sizes. I often end up doing my hair the night before a trip and hoping it lasts the entire time without turning into a complete mess. How do you do it?

See the rest of the Petite Fashion Challenge participants over at Ski Petite!

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  1. says: Ski Petite

    Cute photo. I think shoes are the hardest. I usually try to wear hiking sandals or something when I can, though I didn’t want to admit that in my post :) Thanks for participating!

    1. Thank you for hosting! Packing shoes is the worst! The last time I visited San Francisco, I actually wore 3.5″ heeled booties walking around town! Granted, I was by myself on a shopping excursion and could just walk back to the hotel when I felt my feet getting angry at me, but I walked A LOT that day…crazy! But in Chicago, my heels never even made it out on the town…oh well. :P

  2. Cute outfit- love the scarf (and not a big fan of Missoni) but this looks great on you!

    And re: your curly hair- I LOVE your curly hair  :) I have slick straight hair and want curly hair..LOL

  3. says: daisy351

    They do make mousse in travel size!  Look for it in Target with the other travel sized items.  I believe it’s made by frizz-ease.

    1. OMG…I just did some searching and discovered that my all time favorite mousse comes in a travel size! You’re a genius! I had never seen it in stores, and for some reason never thought to search online. Genius!

  4. says: R.L.

    Love your scarf and it’s so refreshing to see you in flats!  You should wear them more often :)  The Bean as odd as it is, is one of my fav landmarks.  In addition to shoes, the bag is the hardest for me when traveling.  I use a Longchamp tote to carry my DSLR but I’m still looking for a petite-friendly stylish bag that can do a better job.

    1. The Bean is so cool! Very dirty though…lots of weird hand/face marks all over the place…lol. A stylish camera bag is on my mind too, and I’m thinking would make a nice plane carry-on. My camera was wrapped in a scarf and stuffed in my carry-on bag on this trip…bad Kelly! Check these out:

  5. says: Michelle

    LOVE your pictures!! Gorgeous!

    And such a great outfit, too!!

    Hair advice…I am not a mousse user, so no experience there. I usually just use a gloss and hair spray if I do it curly. I am guilty of going to bed with a wet head! I let it air dry a bit before, though. :)

  6. says: Amber

    you look so cute!! i havent been to chicago in forever, even though i live about 30 min away! That hair dilemma doesnt sound fun. Have you ever tried aveda’s little samples? they have a sample of the phomollient that is great for travel. i’ve actually just started using it when i wear my hair curly and it works great (will a little smoothing serum!)

    1. I didn’t know you lived near Chicago! My mom grew up there and my parent’s met there, so I’ve only heard wonderful things about the city!

      I’ve never tried Aveda…hmm…I’ll look for the phomollient sample and do some experimentation. Thanks for the tip! :)

  7. says: Anonymous

    When I’m traveling, I almost always wear flats since I know that even with sneakers, my feet get tired. lol. You look fab and the scarf adds the right amount of color to your outfit! =)

  8. says: Petite LG

    I love Chicago! My husband travels from/to Chicago for work quite often. It’s such a beautiful and fun city. Great outfit, Kelly! I don’t see you in flats very often. I am drooling over your Burb trench =)

    1. Thanks Sydney! The Burb trench was very happy to get her first time out of the closet this season. I wore it every day I was there! And Chicago really won me over. My mom grew up there and my parents met there, so all I ever heard about was how great Chicago is…and it’s true! I had such a great time!

  9. says: Aviva

    I have curly hair just like yours!  I use deva curl and it comes in TSA travel-size bottles, so that makes it easier.  I sometimes scrunch with gel and let it airdry, then put it half up because the top is less curly.  Or I succumb to a messy bun.  My hair would NEVER last a whole trip, one night of sleeping on it and it is a ball of frizz.  Which is why I try to shove my blow dryer and diffuser into my bag whenever I can…Straight-hair girls don’t know how simple they have it!

    1. Oh my goodness…how I wish I had straight hair just for vacations! I was a mess in Costa Rica between the humidity and random rain showers…ugliest I’ve ever looked on vacation…lol. My hair cut is Deva Curl, but I haven’t tried the products. I have a favorite mousse that never lets me down so I’m afraid to switch it up. You know how fickle curly hair can be. ;)

      Do you put your hair up in a loose ponytail on top of your head when you sleep? I know a lot of curly girls do that to help keep their hair looking decent for a second day. I’m a very still sleeper, and have been able to train myself to sleep with my hair draped up over the top of my pillow, which helps a lot. My hair lasted 3 days in Chicago before it was an ugly mess.

      1. says: Aviva

        I never tried that!  Is this this pineapple thing people are mentioning??  Going to to learn.  This could be another curly hair break through for me…thanks Kelly!

  10. says: Cee

    Oh man, hair issues are my biggest problem when traveling too. Mousse comes in a spray can, right? I usually try to stick with gel or some sort of watery alternative and transfer a smaller amount to small bottles. That’s not very helpful =/ But your hair looks gorgeous in these pics! I adore everything about your outfit… especially the socks! I always forget those.

  11. says: Anonymous

    Kelly awesome!!!!  You look fantastic, colder weather suits you ;)

    As for hair, I would also bring my hair dryer and diffuser and hair cream :P  When I go some place with high humidity I don’t bother as it will frizz up on my anyway so I just put it up (I’ll be putting up a tutorial soon on the hair do I did in my “cirque du soleil” post.)  If I’m only gone for a weekend then I will straighten my hair the day before leaving and won’t wash til I get back.  Straight hair is so much easier to care for!!

  12. Wow! I love your trench coat! Very beautiful and perfect for Chicago!
    I checked out Burberry earlier this year but was concerned about the alteration (2 is still too large for petite size) and worried that it might change the design. Any tips for trench coat alteration? :)
    BTW for the hair you could consider an  iron curler.  I use the flat version to straighten my hair and it is very convenient!

    1. Ohh…I certainly do have trench coat alteration tips for you! Firstly, some Burb coats tend to run smaller than others, so ask a sales associate to help point out the smaller ones for you. Second, I haven’t seen it in person yet, but there appears to be a brand new size 0 popping up in some Burb coats online! Third, if you buy your coat at a Burberry boutique, they will do free alterations for you! All the alterations I had done on my coat were completely free (I had it done at the Los Angeles boutique) and I know Jean of got hers done for free as well (Boston). There might be limitations if it’s bought on sale, but I’ve never had a problem or even had to show a receipt. This could vary by boutique though. I had the torso slimmed and sleeves shortened, but have been thinking about taking it in again to get the sleeves slimmed a little too.

  13. says: El.Vi

    ahhh you are by the bean…the best tourist area….I hope you liked chicago…there is sooo much to do. Your outfit is just perfect for fall around here!

  14. says: Erin

    Either I carry a blow dryer and diffuser with me, or I let it air dry at night and use the pineapple technique described at and a silk scarf. Or I wear it up.

  15. says: JJ

    Gooorgeous scarf! It really makes the outfit pop. And as for wanting to wear heels while sightseeing – I’ve done it, and my feet definitely have experienced the fallout from doing so. It’s frustrating finding a pair of shoes you’re comfortable walking in but are also still stylish!

    1. Been there…done that…LOL. I wore 3.5″ booties to shop around town in San Fransisco the last time I was there. My feet KILLED at the end of the day, but darnit, I looked good! I saw a lot of women walking around town in flat boots…maybe that’s the way to go.

  16. says: Anonymous

    I love the Missoni print playing against just a small peek of the classic Burberry check – iconic!  You really can’t go wrong with a timeless piece like the trench – you look both chic and comfortable – perfect combination!

    1. Thank you! Both the trench and scarf are items I’ve been DYING to wear but the weather in SoCal has not worked in my favor just yet. I ended up wearing both of them every day I was in Chicago, so my itch to wear them was finally scratched. :)

  17. says: vix82

    I’m not sure if anyone’s mentioned this already, but Tresemme & John Freida make travel size mousse (under 3.4 oz), which is sold in the travel toiletries section at Target. I believe the formula is for curly hair. 

    Haven’t been able to find it anywhere else besides Target though.

    Good luck!

    1. The travel toiletries section are Target have been a lifesaver for me! So smart of them to dedicate an entire aisle and have a great selection of stuff!

      In any case, I have straight hair and have the same problem with hair products for my carry-on – you never have all the stuff you typically use at home – at least I’ve started bringing my own big brush, instead of a dinky travel-size one!

  18. says: Laura Frost

    Welcome to Chicago! I hope you enjoyed it – it is such a great city. And so true, you just have to wear flats for city walking. 

  19. (sigh) I need a Burberry trench…well, I don’t need one, but I want one.  Funny, I did not like the Missoni stuff when I saw it online, but it looks perfect with this outfit. Love the shoes…I’ve been searching for the perfect pair of flats. I want something like my beloved Bass boat shoes and penny loafers that I literally wore holes in when I was in high school.

  20. says: Irene

    Oh, what you need are nice flats that are MADE for extensive walking – I own a pair that I love from Merrell (and in a beautiful muted red color too – “lava”)! The Merrell Oceania has a thick, textured sole for shock absorption and traction, removable padded insole with arch support, and the top has meshy windows so your toes will stay cool. They are awesome. They’re the only flats I wear now if I know I’ll be walking all day. And I checked for you – Merrell definitely makes them in a size 5! 

  21. says: Thu Huynh

    What a great outfit for sight-seeing! I love trench coat and jeans pairing, so relaxing and chic. I’ve seen this silver bean on many blogs already and love it more each time. Can’t wait to visit that place one day!


  22. says: Anonymous

    Great outfit!!  That the Harbourne right?  Looks nice!  I’ve been thinking about getting one too.  Your trip looked fun and weather looks great (from the photos!).

    When I had permed hair…I used to lug around the hair dryer and diffuser…yes I’m definitely not a light packer.  But I used a product from Schwarzkopf osis that was half cream half gel (can’t find the exact name online!), it was a squeeze bottle so easier to carry around than a can of mousse.

  23. says: Arts

     I wish I had known about this blog 3-4 months back. Would’ve loved to meet up with you on this trip. I live in Chicago (burbs). I’m very petite, trying very hard to be stylish on a budget :)
    love the layering idea…currently it’s freezing here :)

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