Old Kid on the Block

Old Kid on the Block

It’s August 1st, as in… summer is already two months in, how did that happen? It’s probably been the fastest summer yet, and my attempts at consistently sharing posts just that a dream unfulfilled at this rate. But no need to dwell, I’m here now and really loving today’s old school look.

It’s been a fairly mild summer here in Chicago, which means I’ve still been able to wear long sleeves and jeans throughout the season. On a cool summer day, this TopMan (Rest in Peace) shirt felt like a must-have. This sweater-esque look has a built in collar and color blocked stripes in the perfect shades for summer.

When I  put this with a simple and classic wash pair of Levi’s, I felt equal parts touristy dad at Disney and Armie Hammer in Call Me by Your Name, a winning combo, right? There’s a 80’s vibe to this look that I can’t help but love.

Sometimes the best looks are the easiest ones. I  think we all know that a white t-shirt and jeans can be just as attractive and stylish as a bomber or printed shirt.

It’s not always about reinventing the wheel in your closet and finding the newest piece, it can be about bringing an old look back.

Hoping to bring back more old looks, and mindsets here, and soon!

Stay tuned,

TW

Striped for Summer

Striped for Summer

Can we even classify this season as Summer when it’s barely cracked 75 degrees? Probably not, but in a city like Chicago, you’re gonna have to fake it till you make it.

Processed with VSCO with e1 preset

I’m not going to let a dreary summer sky dampen my seasonal wardrobe. I was inspired by June being Pride Month when putting together this look. The look is built around this striped top from Bonobos that I love for summer! In different shades of sherbet, this rainbow print reminds me of a fashionable Pride flag. Seersucker is one of my favorite materials for summer because it’s lightweight and breathable.

This shirt could really work with anything, white jeans, dark denim or khakis. I  thought instead to try a more neutral green to let the shirt pop more. These chinos from Banana Republic Factory are my favorite fitting casual pant. They give a lot of shape and don’t have to be tailored, AMEN!

Processed with VSCO with c8 preset

 

On top, a year round must-have, is this Levi Denim jacket. I  recently purchased this one because the wash is the most neutral and my other denim jacket is too oversized for summer, where let’s face it, fit is crucial. A rope belt and grey loafers are easy accessories to make a little more casual yet cool.

It’s been a while since I’ve put up an outfit post partly due to scheduling and finding motivation, so if you’re reading, thanks for sticking with me 🙂

More summer looks to come, stay tuned!

TW

 

 

Floral Fundamentals

Floral Fundamentals

In the words of Miranda Priestly… “Florals for spring…. groundbreaking.” An iconic line, but an accurate one none the less. But would it be spring without a post about floral prints…. not even close. If the trend isn’t broke, then don’t fix it, right?

Instead of going for my usual bright and cheery floral prints I’m leaning towards a darker and moodier option from Zara. Picked up at the end of the holiday season, I  was immediately drawn to this piece because it reminded me of a water color painting and also looked like a more luxe approach to a spring and summer staple.

CallieCraigWinter-63

I  always feel like Zara does a great job of making something look more expensive than it really is 😉 (that’s always the goal when I’m shopping) So instead of dropping a fortune at All Saints, this seemed like the perfect fit. As it’s been a colder spring anyway, this print transitions perfectly into the season.

With black jeans, it’s a great option for going out, but I’m excited to pair it with a bomber or blazer for a nice pop of color and pattern. Being from Zara, that means I’ve seen this top on others, and it honestly fits nicely on every body shape as it’s a bit loose.

CallieCraigWinter-60

Although floral prints might not be “groundbreaking” there is always a way to break new ground on how you approach a trend. For me, it’s taking a more dramatic route with a classic. I’m not sure about you, but I’m READY to start wearing spring clothes, it’s practically April, let’s get this season in bloom.

-TW

Pop of Preppy

Pop of Preppy

It’s been a hot minute… or month, since I’ve posted about an outfit. Perhaps I’m distracted by all my bachelor posts or perhaps I’m just overwhelmed with how crazy busy the last couple of months have been. Either way, I  finally have a chance to sit down and break down a new look.

With years of prep school under my belt, I used to be extremely preppy. At the time, I  thought I  was EVERYTHING in my Vineyard Vines, seersucker pants and the latest Sperry’s. Just the thought of some of things I used to wear, yikes! When I moved to Chicago and realized I was a pastel fish out of water, I started adopted a more city-friendly look.

CallieCraigWinter-19

At my core though, there is a still a little bit of a preppy left in me. With today’s look, I  feel like I’ve been able to merge together a more modern preppy aesthetic without looking too “school boy.” The look is really entered around this TopMan white sweater with striped neckline. White is not usually my first color choice, but the bold stripe reminded me of a collegiate style sweater that could be come an instant classic. Winter whites are always very fashion forward too.

If I  were to pair this with khakis and a white button up, I think it’d start to look like a school uniform. Instead, a navy turtleneck and blue plaid pants break this up and make the whole outfit more contemporary.

When it comes to style, we can never truly change our spots completely. That’s me when it comes to being preppy, and that’s not necessarily a bad thing. Once the weather starts to break, hopefully I’ll be able to share more outfit ideas.

Stayed tuned for developments with Bachelor, home design, travel and fashion soon!

-TW

Blue Velvet

Blue Velvet

We’re officially one week into January and resolutions are still in play, the new season of The Bachelor has started (and I already despise all the girls) and I’m back with a new look post to start the year off stylish.

The start of a very long winter typically makes sweatpants and bulky sweater even more appealing than usual. I’m trying my best to make sure I  try to shy away from my tendencies and embrace dressy looks and try new options the season. This look is a great example of that. I’ve already welcomed turtlenecks with open arms, but now it’s about how to pull in other pieces like blazers to dress them up.

calliecraigwinter-2

This navy velvet blazer is a such a show stopper in this winter look. Against my white turtleneck from Uniqlo is great for a day at work when you’re feeling a little fancy and even better for night out in the winter. Instead of going for the standard khakis or black pants, I  went for a cobalt blue color, to add an extra pop. A pair of printed pants would be another way to add texture to the look!

I  love this look because it’s just an easy way to elevate a rather easy winter ensemble. Anytime you add color, texture, or pattern, especially with basic pieces, it’s a win. Here’s to hoping our outfits and resolutions remain in tact as we get through the first month of the new year!

-TW

Wrapped in Red

Wrapped in Red

Four days till Christmas, how in the hell did that happen? As we know, presents have been purchased are wrapped, but when it comes to other holiday actives, I’m coming up a bit short.

CallieCraigWinter-42

Everyone usually has at least one holiday party to go to, whether you’re hosting one, heading to a friend’s, or going to your work party, a good outfit is crucial. I  hosted a small get together earlier in the month, and then headed to my work Christmas party this week and made sure to have a holiday outfit lined up for each.

IMG_3863

Although it is fun to wear the ugly sweaters, the light up ears, etc, this look is a more classic and modern taken on the red and green color scheme that most Christmas looks call for. I  love both of these pieces on their own, and was happy to see they could work well together for the holidays.

The red cotton shirt was an amazing sale find while I  was in London this summer. The deep crimson color works nicely as a pop of color. A similar style is here. It works well with jeans or in my case, dress pants.

I  saw these trousers at Oak + Fort, and knew that I had to have them. The olive plaid print with the black pipping down the side is a nice detail. Pants like these are a nice twist on any basic pair of pants for the office. They’re cut a bit short, so long boots with coordinating socks make sure I don’t loose height.

With an oversized scarf and camel coat over the look, I’m ready for whatever holiday activities are ahead. I hope everyone goes into the final push towards holiday with high hopes for a Merry Christmas!

Happy Holidays,

TW

Polar Express

Polar Express

It’s been quite a fast and excited holiday season so far! I’ve barely had a chance to catch up after an amazing and much needed respite in the tropics and heading right back into work full steam ahead before Christmas. Coming back from a island vacation means fasting the harsh reality that freezing temperatures are here and here to stay. The only thing that’s a positive is that that means layers and more looks.

Processed with VSCO with e3 preset

I  got a chance to work with both Express and Banana Republic to come up with a winter look that works perfectly as a transition to these colder days ahead. I’ve been loving these dark floral patterned prints as a way to nod to fall but in a color palette more appropriate for winter. They’re great for layered with dark tees as well! This shirt pairs perfectly with these black fitted black chinos from Banana Republic Factory.

I  cannot stress how great these pants fit! Slim but not too slim, and give a lot of shape through the hips and back! I  think it’s easy to go for jeans when it gets colder, but a great fitting pant should be the next best option sitting in your closet.

Processed with VSCO with e3 preset

An easy bomber, this one is TopMan, in a charcoaled navy color, makes for an easy throw on peace to make this outfit more nighttime friendly. I’m looking forward to digging into my closet for more winter looks with plenty of layers and patterns coming soon.

Happy Friday,

TW