Fashion Flub: Hats

I already told ya’ll that I have a rough time wearing scarves

well I have another accessory nemesis:


I want to wear them SO badly, but every time I pick one up, it ends up staying in my closet for the entire season. It’s funny though because I have no prob wearing hats with my swimsuit, it’s out in public where I have issues.

me (6)

(Pool time = the only time I’ll wear hats)

I blame it on many things:

My funny-shaped head.

The fact that I have no clue what to wear with them.

and that the Pilot isn’t a hat fan.

Every time I see a girl rocking a hat, I think it looks SO cute. I especially love winter hats- functional and fashionable.

jessica_alba_hat_picture-1253561445 hats_off_to_cameron_diaz


Here are some of my faves:

image Banana Republic

(Olive is a great neutral color)

image Juicy Couture

image Saks

image Anthropologie

Do you wear hats? Any tips??

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  1. I have the same difficulty wearing hats and scarves. Accessories elude me!
    But I also live in Florida so scarves would be a bit much like 90% of time. And hats…I dunno. I feel like my hair needs to be free. Oh well! I just keep it simple for now.

  2. Hats are my scary accessory, too. It would be nice to have a bad hair day option BESIDES a ponytail, though!

  3. Like you, I am unable to pull the trigger on the fedora. However. I am a champion of the winter hat (goes with my scarf wearing, I live in Minnesota). My sister is also an amazing knitter and has knit me plenty of those adorable slouchy types!

  4. I’ve been wearing a lot of hats lately! I’ll throw on a baseball cap when I take the dog for a walk in the morning and my hair has yet to see a brush. I have the fedora type hat that I wear at the pool/beach. Winter hats (like stocking caps) don’t look good on me at all, though.

  5. I think hats are adorable, but my hair is too damn curly to wear any of the ones I like! I end up looking like Bozo.

  6. I thought I was the only one with a hat issue. If there’s one that does fit my (giant?) head, it looks odd. Not sure if that’s due to not being used to seeing them on or if I should just stay away. All styles/fabrics are a problem. I did manage to find a giant floppy straw one from J Crew I didn’t hate, plus I picked up a couple of those driving cap ones from Gap because the husband said they actually looked good on me- depends on what you wear them with, too.

  7. To me, winter hats are meant to be silly. Everyone looks funny in them, but they are so necessary for warmth. I go for ones in bright colors with huge pompoms on top. I also have an especially silly looking one from Russia that kinda resembles a helmet. Have fun with it and if you aren’t sure, get your hats at walmart or target so it isn’t much of a loss if you don’t wear it so much!

  8. I’m not a hat person at all! I always think they look cute though 🙂

  9. I have a massive head so most hats don’t fit me. 🙁

  10. I just went hat shopping this past weekend and it was a disaster! I must have a small head because everything just looked like it was eating me alive. It was very sad.

  11. There is no other way to wear a hat than with confidence!

  12. I used to have the same issue, but I had been longing after a Panama hat for so long. They just looked adorable on everyone else. So when J.Crew had them, I bought one. It was a $50 investment, so not only does the money spent make me wear it whenever possible, but so does the mindset that, hell, wear what you want as long as you wear it confidently. I throw it on with pretty much anything…as long as I’m not working!

  13. I love hats when my hair is long. It just doesn’t work when my hair is short. So I guess the only tip I have it either wear your hair down or possibly in a low side ponytail if you choose to wear a hat. I think they would look cute on you!

  14. Melissa says:

    I think you’d look great in a hat with your hair!

    Scarves and winter hats come naturally to all of us Canadians. But it also gets hot as heck here in the summer and you can rock a floppy straw hat — pool side, beach, gardening. As for a fedora, stick to wearing it when you will be mostly outside.. out for a walk with Bella or the Pilot, anywhere you can wear a bigger floppy hat, outdoor shopping like farmers markets etc.. Once you get used to wearing them, you won’t think anything of it.

  15. I’m with ya on this one too. Hats are intimidating! I don’t even like wearing baseballs hats, let alone fashionable ones. I always just think they look ridiculous on me.

  16. I wear baseball caps daily! I used to have awesome long hair; But Chemo took it from me! So now I have short hair, and I’m OK with that, it is the frizzy mess I can’t deal with! I just wear hats instead! People don’t recognize me without one anymore!

  17. Katheryn says:

    I love wearing hats! Hubby definitely agrees I have a hat problem since I think I own close to 20 hats now. Unfortunately, I don’t really have any tips. I love them, so I wear them! I have dressy, casual, hip, winter, summer – you name it.

  18. Siiigh. I WISH I could wear hats! I have a ginormous head!!! It’s humungo. I find that hats always look so off on me, but I really want a big floppy hat for this summer, just like the juicy one you posted. I think they are so cute!

  19. i love hats and like you, i only wear it when i’m wearing a bathing suit!! but i really wanna try wearing it more out in public. love that one with jessica alba. she’s wearing jeans, white shirt and a hat. perfection.

  20. The two things (for me) required for hats are a) the right hairstyle and b) confidence! My hair looks best in a hat, when worn down, parted down the middle with some texture. When I wear it up, it looks best in a messy side bun. But most importantly, you have to own it. 🙂
    You would look so cute in that fedora!

  21. I think hats are super cute!! The problem is, I don’t think I can pull off the hat look (as much as I’d like to think I do) and yet I always seem to pick up trendy looking hats at the store…and now there’s a place in my closet for the hats I DON’T wear. It’s kind of a problem…it might be my huge curly hair that gets in the way of my pulling off the hat look? Anyway, maybe you should try rocking the hat look in public!! It might work in your favor? 🙂

  22. Michelle says:

    Fake it until you make it…or however that saying goes. I was the same as you. I would buy a cute hat, but everytime it came down to actually wearing it, I would chicken out. I finally figured out that you just have to start wearing them & at some point you will feel comfortable in hats. The numerous compliments you receive will help build your confidence too!

  23. I’m on the same boat as you. I love how hats look on OTHER people but never on me. I’ve tried different styles but haven’t found one for me yet. 🙁

  24. I am not a hat girl, at all.

    I don’t think they look good on me and I don’t like putting things on my head…it makes my head itch and feel weird. lol

    I love seeing hats on others but on myself? meh…Not for me.

    I actually totally think you could pull of a great slouchy hat or really any kind…i think you would look great in it!

  25. I love hats, although I sometimes feel totally silly in them. I have an amazing fedora from a hat shop in New Orleans that i adore, but I sometimes feel like the odd man out to sport one when we’re going out on weekends… I really do need to wear it more though!

  26. I love hats too! Besides beach or poolside, I like wearing them to outdoor concerts. I never buy expensive ones, so if they only make it out of he closet a couple times a year, I don’t feel guilty. Target actually makes some really cute ones

  27. I love hats and always wear them.. and I spend too much time admiring them at stores. I think with hats, you just have to really OWN it and be confident when you’re wearing it. They’re fun and so so cute, not serious. That’s what I like most about them!

  28. Jessica says:

    I do the same with hats! I really want a summer fedora now. I have one for the winter and I didn’t wear it last season. I should def wear it this coming winter. I had this look in mind when I got it:

    ps. I LOVE SATC!!!!

  29. The case of hats is…buy one and actually wear it, I think a lot of people think they look funny in hats when they don’t at all! Keep all of your other accessories simple so you feel more comfortable…think loose white tee or flowy blouse with bell bottom jeans.

  30. I wear winter hats to keep warm, but other than that I never wear them. I think they look ridiculous on me! 😛

  31. I am a hat wearer, I was blessed with looking okay in them. I usually try to put my hair in a side (not totally on the side, butt off center) messy bun with my hats and leave some bangs down so I don’t look like a total boy 🙂 I really want a Fedora to be my next hat!

  32. Hats are a toughie, but I cannot wear maxi dresses! I always feel too dressed up in them. Also, I’m about 5’7 and a size 8-10 and I feel like anyone except a very tall, very thin girl in a maxi looks just like they’re trying to hide a body flaw. Also iPhone keeps changing maxi into Nazi… So I’ll end here, haha.

  33. I’m not usually a hat person either, but I love the black cloche from Saks you have pictured. I also think it is easier to try to wear hats more when it’s colder, because then you can try it with lots of different clothes/hairstyles without worrying about overheating. 😉

  34. ah you’d look so cute in a hat! Get one!

  35. My hubby hates when I try and wear anything on my head. Scarfs, headbands, hats, fruit baskets. I can’t pull them off. I do sport my Phillies hat at the pool though. I think I look cute in baseball hats, he has to agree bc he buys them for me. I bet you would pull off one of those large floppy pool hats, can see it looking adorable on you!

  36. I love hats! I used to be afraid to wear them too but then I got really into them. I think eventually you will figure it out 🙂

  37. I really think hats are all about two things: a) confidence and b) the ability to keep it on all day (especially if you have fine, hat-hair-prone strands like mine). If you’re gonna wear a hat and fidget with it/feel self-conscious, better to just skip it. Likewise, if you’re going places that will require you to take it on and off all day, better to not risk losing it or ending up with a funky hair day—save it for a time when you can incorporate it into your outfit and rock it without worry. I just discovered the magic of hats this year and I’ve loved experimenting with everything from floppy 70’s felt hats to straw fedoras. A good transition piece to try is those turban headbands that are so popular right now…a little more flair than a classic headband, but not quite a straight-up hat with all the attached implications.

    Just live your life like Carrie Bradshaw and PUT.A.BIRD.ON.IT.

  38. I love hats, too but I have funny ears and wearing a hat exposes them which makes me feel VERY self concious! HAHA!

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