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Ask Belle: Dressing Up Leggings

Dear Belle,

My fiance and I are headed to Europe next month, and I’m so excited.  The flight is eight hours and I want to wear leggings.  Is there a way to dress them up so I don’t look like a gym rat?  I can’t wait to see your suggestions.

Sincerely, Anna

First, looking good in leggings is about choosing the right leggings.  You want a pair that are thick and good quality.  Thin leggings look cheap.  I like Zella Live In leggings or Lululemon Wunder Under leggings.  For flying or driving in the car, I like the Wunder Under leggings because they fit snugly but comfortably.

As for how to style them, here are three suggestions.

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Left, Damask Print Scarf ($38) // Boden Boy Fit Shirt ($89) // Steven Emmery Tall Boots ($179)

Center, Sole Society Flynn Booties ($109) // Stone Stud Earrings ($29) // Betsey Johnson Wide Belt ($10) // Twin-set Knitted Sweater Dress ($245)

Right, Rebel Pendant ($79) // River Island Cocoon Cardigan ($76) // New Balance 620 Sneakers ($80) // Free People Anna Long Sleeve Tee ($58)

***

These simple, casual outfits look chic but are totally comfortable.  The outfit on the left mixes a long button-up shirt with a slouchy boot and printed scarf.  Seriously, how cute are those boots?  I love the relaxed look.  Searching for a leather option under-$150?  These Rockport Tristina Boots look great and are incredibly comfy.

The top is from Boden.  I own it in white and I love it.  If you’re pear-shaped, I recommend buying the size that fits your torso and having a tailor add side vents to give you some room in the hip.  For something a bit shorter, try Boden’s Girl Fit Shirt.

A sweaterdress is always a great option.  I like this teal dress from FarFetch; sadly, it’s a bit more than I want to spend.  For a more affordable option, this off-the-shoulder option from Missguided would be cute with a tank under it.  And this $80 cable-knit dress form BB Dakota is a total classic.

I added this very inexpensive belt from Nordstrom Rack for a little bit of shape.  I also like this Ralph Lauren belt with a braided accent.  As for the boots, the thicker heel makes them more comfortable for walking and the knot detail makes them extra cool.  Prefer a flat boot?  Try these flat Michael Kors bootie with a tie on the back.

The last look is my favorite.  A long tunic with a cozy sweater is my ultimate weekend look, and it keeps you cozy on a long flight.  Also, how amazing is this sweater for $76?  If you want something that doubles as work attire, the MM LaFleur Morandi sweater is impossibly warm and worth every penny.  I added my favorite Stella & Dot necklace and a cool sneaker, which I also own, to finish the look.  This layered ensemble is perfectly put together and completely relaxed.

LEAVE A COMMENT

    19 comments

  1. LadyLawyer12 says:

    I wore that pair of gold new balances all over Italy and am currently wearing them on a train north for a weekend away. Cannot say enough good things about them. Comfy and stylish. You can pair them with anything. I have on a black cotton dress and gold pendant necklace with them now.

    September 23, 2016/Reply
  2. AS says:

    I love the HUE brand leggings! I got mine at Nordstrom. They come in grey and black, and sometimes they go on sale.

    September 23, 2016/Reply
  3. Anna says:

    Ugh, that MM La Fleur sweater is perfection. Why does it have to be soooooo pricey?!?!?! Dressing for planes is so much easier in the winter than summer. These are all great outfits, but for your own sanity and that of those in line behind you, only wear the tall boots if you have Pre-Check. Dealing with tall boots as you’re going through security, especially if it’s a busy time at the airport, is incredibly annoying.

    September 23, 2016/Reply
    • Belle says:

      It is worth every penny. I have the brown one, I’m buying the grey. You will wear it all the time. I swear.

      September 23, 2016/Reply
  4. Melissa says:

    Love the looks, but I’d advise against flying in tall boots. I flew Vancouver to Toronto (about 5 hours) a few years ago in riding style boots. By calves were aching part way through the flight due to the inevitable swelling, so I unzipped them. Couldn’t zip them back up after the flight. Walking through arrivals with floppy boot tops = not a good look!

    September 23, 2016/Reply
    • Anna says:

      Eeek, yeah, definitely not good for a long flight. I would only wear them on flights under 3.5 hours. You also want to be able to slip off your shoes (and have appropriate socks) on long-haul flights, and boots would be a pain for that too.

      September 23, 2016/Reply
    • Belle says:

      You might try a pair of compression socks if you get that kind of swelling. I do, and it’s a big help.

      September 23, 2016/Reply
  5. CLS says:

    I love all these suggestions. We’re heading out to Spain in November with our 7 year old and I totally need more suggestions as to what to bring that’s comfy, stylish and easy to move around in, as we won’t be going anywhere too fancy with a 7 year old… I might just have to buy those NB, they look fabulous! I also tend to default to my gray chucks. Man, I love those sneakers. Any other suggestions from you ladies about a cute, comfy shoe that are versatile? THinking something that has some support, but relatively flat, as we’ll be walking everywhere.

    Also, what DOES one wear to a soccer match in Spain? Any ideas??

    I’m so glad this post was started – it’s exactly what I was thinking too. 🙂

    September 23, 2016/Reply
    • Anna says:

      Those sneakers are pretty cute. Spaniards, like most continental Europeans, look fairly polished, even in casual clothes, but it’s a practical kind of polished. Lots of scarves, loose fitting tops with fitted bottoms, flat boots, and ballet flats, A lot of Spanish shoe brands are also known for combining style and comfort, so you might want to do some shopping there (you can get your VAT refunded at the airport so it’s an even better deal than finding those brands here). I bought a super cute pair of Geox flats that are the best flats I’ve ever owned, and were about $30 less than if I’d bought them stateside. Camper is also a well-known brand. The exception would be the soccer match, that’s super casual. Think American football game. Wear the team’s color if you don’t have a jersey.

      September 23, 2016/Reply
  6. NS says:

    Belle, you’re some kind of superstar! HOW do you create such chic looks — I’ve walked around airports looking like a (very comfy) hobo. Buying everything you recommended right now!

    September 23, 2016/Reply
    • Allison says:

      I just got back from Amsterdam and Belgium and everyone’s wearing stan smith’s. My coworker just got back from Madrid and Barcelona and said the same thing. Best travel shoe ever.

      September 23, 2016/Reply
  7. Denise says:

    I actually prefer to wear my tall boots in the plane…then you don’t have to worry about them taking up space in your luggage! Definitely go for the pre check and add global entry – $85 for 5 years and immigration becomes so easy, no long lines!

    September 23, 2016/Reply
  8. Alexandria Knox GOP Intern says:

    Belle, again amazing posts. I am wondering if any of you guys could help me. I am a political campaign intern and am also have been a candidate for state representative and plan to run again. I have been chosen for a scholarship to attend a student leadership week long retreat and want to dress casual but professional. I thought about doing the khakis polo shirts brown oxfords thing but probably would look really intern, but I don’t want to bring expensive clotheing since it will be in the woods in a camp environment. I don’t know about bringing sneakers either as these might be too casual as I will be helping with some promotional videos. Would brown and black oxfords with nice shirts, cardigans, and nice jeans and khakis work for the trip? Thank you for any advice.

    September 23, 2016/Reply
  9. Kate says:

    So, on leggings: I’m short. I have a couple pairs of the Zella Live-Ins, but they’re long, so they’re either bunched at my ankles or folded under. Is it completely silly to take leggings to the seamstress to be hemmed?

    September 23, 2016/Reply
    • rar says:

      whoops, just responded to the wrong comment re: hemming leggings (see below).

      September 25, 2016/Reply
      • Kate says:

        Ha! No worries. I’ve definitely taken advantage many times of Lululemon’s alteration service. I also prefer buying jeans at Nordstrom, as I always need to get jeans hemmed and they do it for free if you’re buying at full price. I might take a couple pairs to my seamstress the next time I need to get something else done and see what they say.

        September 25, 2016/Reply
  10. Fashionista says:

    Love the looks! So cute 😉

    September 23, 2016/Reply
    • rar says:

      Nordstrom might do it for you. Lululemon offers the service for free, so it’s not unheard of.

      September 25, 2016/Reply
  11. Catherine says:

    Wow! I just bought a pair of Zella leggings (Nordstrom is FINALLY in Canada!) – and I’m going to mix and match what I can in my wardrobe to emulate these looks. That sweater dress is absolutely divine!

    September 24, 2016/Reply