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Wingtip Profile: Trevor Olson


Trevor Olson is your typical midwestern boy: hails from a small town, owns a cheese hat and jets off to Milan for months on end where he appears in editorials and fashion shows seen around the world. Though he has built quite the resume in the past couple years, the 24-year-old Wisconsin native never grew up wanting to be on the runway. In fact, before modeling, Olson attended a technical college where he studied cabinetmaking and millwork. However, following many comments that stated he should have a career in front of the camera, Olson decided to embark on a new beginning.

After signing with a local agency in Madison, Wis., Olson attended a modeling and talent recruiting event where he caught the eye of representatives at Wilhelmina in Los Angeles. Since then, Olson has appeared in ads for European brands like Belmont 1938 and Manuel Ritz as well as posing in GQ Italy, L’uomo Vogue, Gentlemen and — more recently — fronting the cover of Wallpaper Magazine.

Fresh off the Fall 2015 runway, Olson sat down via Skype with WTJ to discuss his start in the industry, favorite moments and plans for the future.



Wingtip Jungle: How did you get started in modeling?

Trevor Olson: It’s never a simple answer to give for this. I had some people ask me if I ever considered modeling and I thought it would be cool, so I searched online for modeling agencies and I found one in Madison, The Rock. I emailed them and set up an open call. From there we set up a test shoot and once they got the pictures, they decided they wanted to sign me. After I signed with them, I went to IMTA and got interest from Wilhelmina in Los Angeles. So I went out there for three months to start.


WTJ: What is it like when you first start out?

TO: In the beginning, when you’re inexperienced, it’s nerve wracking because you don’t know how to act and don’t know what people want or how you’re supposed to act, how your hair’s supposed to be, your body, your skin — everything. It’s mostly the confidence thing you don’t understand because you don’t know what you’re doing.




WTJ: What is a day in the life of a model look like?

TO: I usually wake up and go to a couple castings — especially in Milan, there are castings almost every day. You go with your book, wait in line for a bit, take some pictures and maybe try on clothes to see how they look. Sometimes I will go to my agency and see what they have coming up for the next week and then go to fittings if I’m going to be walking in a show. I like having things structured because if I don’t have anything scheduled, I’ll do nothing.


WTJ: What is it like backstage at a fashion show?

TO: It’s crazy, but a lot of fun. There’s always a lot of backstage photographers yelling at you and asking you to look over there or walk for them. Then you have people making sure you get your hair and makeup done and a bunch of other stuff. It’s really intense. Once you get off the runway, there’s more people that want to take pictures of you but then you have to go get your outfit changed with your personal dresser. So you throw your clothes down and then they’re helping you get dressed. You actually get to know the other models and the people doing your hair and makeup too.


Courtesy of Belmonte 1938

Courtesy of Belmonte 1938


WTJ: What has been your favorite shoot?

TO: I was in Italy for a brand called Belmonte and it was up in the Dolomite mountain range, which is the same as the alps. We were up in the mountains in a cabin and we went around and took pictures with huskies and it was a super cool shoot because it was relaxed and we were out in nature enjoying the scenery.


WTJ: What is the best skin-care tip you have learned while modeling?

TO: You don’t need to use a bunch of creams. I think it’s about getting to know your individual skin, because I have some friends that will do one shoot and then they will break out all over the place, but because my skin is so dry, I don’t usually get acne. I put hand moisturizer on my face — I wouldn’t say that’s my beauty tip because everyone says it’s the worst thing to do. Moisturize and sunscreen — I’m pretty lazy with taking care of my skin.



WTJ: Funniest moment?

TO: One time when I was doing a job, I came in and the photographer looked at me and said, “Thank God you’re here, because these clothes are terrible.” 


WTJ: Do you see yourself relocating to a larger city where modeling is more readily available?

TO: I want to go to New York — but nothing seems to go as planned. I was suppose to go to New York this past month but then came back to Milan for three months. I like living in the big city, but I also like going home and getting away from all the noise and people.


WTJ: What are your future goals and aspirations?

TO: I don’t put a time frame on anything. Right now I’m enjoying this and seeing where it goes. I already stress enough in life so I’m trying not to think about it. I don’t have any goals — I haven’t had goals since 8th grade when they told us we needed to start planning for our future. I guess I just want to be happy with whatever I’m doing in the future.



Courtesy of Manuel Ritz

Courtesy of Manuel Ritz

Courtesy of Manuel Ritz

Courtesy of Manuel Ritz


Courtesy of GQ Italy

Courtesy of GQ Italy



— John Soper

Because you can still wear buffalo plaid





Photo by George Evan / Instagram: @GeorgeEvanPhoto / Twitter: @TheGeorgeEvan

After the Holidays we thought we might go off the deep end if we saw one more ounce of red plaid. That being said, we’ve had some time off from the good-tidings and realized it’s still cold, and it’s January. We picked up this cropped 1940’s buffalo check jacket and 1960’s repaired fedora for less than $50 each at the Melrose Flea Market in LA and decided to give them some love. When paired back to black basics and a neutral boot, your look is mid-week, errand running gold.




Perfect shearling style








Photo by George Evan / Instagram: @GeorgeEvanPhoto / Twitter: @TheGeorgeEvan


We’re taking our bomber jacket into fresh territory post Holidaze by pairing with cream jeans and neutral staples. (If you haven’ already, be sure to erase those silly rules about white jeans and Labor day out of your memory). Aviator sunnies keep this look Top Gun friendly, but it will be clear you are not heading to a costume party.

Santa Buddy, Slip a Little Something Under the T...


All of this Christmas shopping we’ve been up to is giving us the urge to splurge on something tiny for ourselves.

Just for fun — and in hopes that one of our generous readers wanted to buy us something — we decided to compile our ‘Grownup Christmas List.’ However, unlike the Kelly Clarkson song, instead of no more lies and wars, we picked out our favorite wish-I-may-wish-I-might luxury items. Sorry we’re not sorry.

Check out our picks after the jump.

(Photo Courtesy of Vianel)

We asked. They told. (and told, and told)


Let’s get real, unless you’re a mind reader like Mel Gibson in ‘What Women Want,’ you’re likely clueless as to what your girlfriend/sister/mother/BFF wants for the holidays. Join the club. Since we here at WTJ are just about as ill-informed as you, we decided to invest in the help from some of our favorite female bloggers and insta-favs. We asked them to show us what they’re asking their men for this Christmas, just in time for you to step up your gift game.


Lauren R. – Williamsburg, Brooklyn.  
Instagram: @TheStylevore

  1. This teeth whitening combo could quite possibly be the most romantic gift a guy can gift his gal.
  2. What gal doesn’t get parched in the middle of the night? Keep this beautiful carafe and glass set bedside to stay hydrated…or put wine in it, whatever.
  3. Help your gal look festive this holiday season with our fav hair accessories.
  4. We are huge fans of this bag line…”Oversized Lady” is so chic and feminine. A must have for your special (over or under) sized lady.
  5. We love this 3D twist on the charm necklace repin’ peace & love.
  6. Ummmm…”shower wine“? yes, please.
  7. Who wouldn’t want to get a box of marshmallows featuring your fav images? Added bonus…you can always make s’mores if you’re not feeling any of the pics.
  8. If you’re a lady and you MUST scrape the ice off your car windows solo you might as well do it in style.



Give Good Gift: UNDER $100

This Holiday, our team has rifled through the cyber mess and weeded through the junk to put together a specially edited shop of the BEST gifts for under $100.

We’ve kept things simple and put everything right here on our homepage, just click…shop…score.  We’ll keep this note short, and the product lists long, so go ahead…whip out your wallets and fire up the macbook, you’re in for a treat (without the mess):


Give Thanks.


We’ve taken a break from stuffing ourselves to drop you all a quick note. Thank you so much for all of the support and site-lovin this year. Just last January we decided to try our hand at a little blogging… never did we think it would take off like it has. We’re truly thankful for your support.

Much love,


We (sadly) just came back to the arctic from a west coast jaunt and had a blast (especially visiting our Spotify BFF @littlemiala). Los Angeles & Vegas were our stops of choice and with a bit of west coast chill in the air, we opted for layered flannels, tees, and lightweight bombers. 

We raided our iPhone & Instagram for some warm weather flashbacks to perk our spirits while waiting for the ice to melt in Manhattan. 

H&M Pilot Jacket / AEO Slouch Slub Tee / AEO Workwear Flannel / AEO Premium Grey Slim Denim / Hightop Chuck Taylor / Louis Vuitton Carryall Travel Bag

The mountain views between LA and Vegas never get old (and are INSTA heaven)
Belstaff Kendall Moto Jacket & Aviators for a lunch at Lemonade with @littlemiala
It’s in the bag.
Working and playing in New York City, we never know what we’ll be doing from one minute to the next. We keep a good bag of tricks for whatever comes our way. 

Big work meeting at 9am? Check. Drinks with friends after work at 7? Check. What?! A bike is available in Conor’s Soul Cycle class at 8 tonight?! Check.  

Burn Notice.
After a recent working lunch at ABC Kitchen in Manhattan, we decided to take a stroll through the main floor of ABC Home and came across our new obsession, ‘Eclectic’ candles by Tom Dixon. Inspired by British heritage and not remotely ‘girly; these cool candles will elevate the vibe of any room…breaking down the burns, after the jump.
Royalty (left): Earl Grey tea, scones, strawberry jam & a ride in a 1950’s Bentley (beat up leather seats, clearly)

London (center): Red bricks, london parks, crocus, and the salty scent of the River Themes

Orientalist (right): Cinnamon sticks, musk & Chinese herbals

Shop Tom Dixon scents.

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