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

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.

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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.

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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

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.

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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.

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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

Red-y for Fall

Red-y for Fall

The Instagram feeds are clogged with pumpkins, the leaves are changing and Chicago went from 82 to 38 overnight, which only means one thing… fall is fully flourishing and I’ve been ready for it, or should I say… RED-y for it.

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Red has never been my color, but I’m trying to change that this year. Just like those mustard tones from my recent posts, I’m experimenting with being bolder with red. The best way to do it is to just go for it, so pairing this Ben Sherman knit with my favorite crimson vintage letterman’s jacket made a bright statement.

The long sleeve knit was a sale piece I picked up in London, for just 18£ which is practically nothing by their standards. Long sleeve pieces like this are great placeholders before I have to bust out a sweater and scarf. 

The change in weather has inspired me to really start stepping out in style in this Fall, and I’m RED-y for it! Are you?

-TW

Out & About

Out & About

2018 is proving to be quite overwhelming, wouldn’t you say? It’s been a pretty heavy year full of social and political issues rising to the surface on what seems like a daily basis, I mean, we’re living in a time where Colton is the next Bachelor!

Jokes aside, in times like this, its sometimes nice to have reflection on something positive. Just a few years ago, I wasn’t even aware that today is National Coming Out Day, set aside to celebrate the process of coming out in the LGBT community and at a time like this, I  figured it’s nice to take a day from all the negativity we’re seeing and appreciate that I’m fortunate enough to be out and have so many great friends and a loving family that support me no matter what.

Coming out is a very personal experience, and no two stories are the same, but they are all equally important! For some people it’s painless, others, traumatizing, but each is just as brave as the next and deserves to celebrate that part of their journey of identity and self acceptance.

Let’s face it, coming out isn’t a one time gig, it happens many times, over many years. Even in 2018, given everything we hear and see on the news, it’s not exactly a welcoming environment to come out. There is a still a lot of ignorance out there, and I’ve always admired my peers who handle it with grace. I’m glad we have days like to day to celebrate such a big personal milestone for LGBT people. So thank you to all of those who support their friends and remember that you play an important role in the process. Here’s to appreciating everyone celebrating having come out, or those finding courage to come out in the future.

More posts to come soon, thanks for reading!

TW

 

 

Dropping a Bomb(er)

Dropping a Bomb(er)

It starting to feel a lot like fall, and thank the LORD! Chicago isn’t exactly covered in fall foliage but a consistent drop in temperatures is at least allowing me to wear jeans and boots on the regular. With the new season in full effect, I’ve decided to try and elevate my fall looks more than I  have in year’s past.  Today’s outfit is truly the bomb… (bad pun) because it’s centered on one of my favorite bomber jackets.

CallieCraigWAS091818-65Sometimes I feel like I’m Karamo from Queer Eye with the amount of jackets and bombers I own and wear on a regular basis. This bomber, however, is perhaps them best of all of them. A birthday present to myself a few years back, this maroon jacket is the perfect piece to build a luxe fall look around.

Not only am I in love in the deep burgundy color, but the silky material that makes this $75 bomber look like it was triple the price. (God bless H&M sometimes) It’s one of those pieces that takes any look from good to great and this is no exception.

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Usually I  wear this bomber for a nighttime event with dress pants and a dress shirt, but for a fall day to night look, I  paired it with a chambray button down and black denim. I’m loving the result. it

The best part of bomber jackets, especially one as sleek as this one, is that it can take any look and truly become a wow moment. Bringing it back to Karamo and the cast of Queer Eye, but truly they all know how to dress and have the perfect blend of chic daytime looks that I  hope to wear more in and outside of the office.

Here’s to making this fall my most stylish fall yet!

-TW