High-End & Low-End feat. Anthony Ollmann

February 14th, 2014

I love “started from the bottom” stories, especially as they relate to individuals who’ve worked hard, stayed humble, and put as much energy into enjoying the ride as reaching the destination.

Anthony Ollmann grew up in Grand Rapids Michigan, far from any high-fashion scene. He started his career in fashion at one of the only industry jobs available in his hometown: the sales floor at Old Navy. Through a series of promotions and head hunts, he gradually worked his way up the fashion ladder. Ten years later he’s now in charge of the West Coat made-to-measure program at Gucci, where he styles and fits tailored garments for a powerful book of A-list clientele.

More impressive than all of his fancy work on Rodeo Drive is the fact that Anthony has remained the cool, down-to-earth, fun loving guy he’s always been. He’s a guy’s guy from the northern Midwest who just happens to be managing one of the most prestigious brands in the world.

What I love about Anthony’s personal style is that he seamlessly mixes high-end designer brands, like Gucci, with low-end affordable brands like the Gap, Banana Republic, and H&M.

“I didn’t grow up with money. I would look at these magazines and get a little depressed because the idea of spending $3,000 on a suit was absurd. I had to learn how to cheat looks.  To mix labels and learn what to spend money on and what I could use to fill in the gaps…because, in the end, style is not about labels.”

We got together with Anthony to give you a taste of his High/Low personal style and where it all comes from.

    1. Layered & Tailored


    “My father had amazing style. He is a man’s man. I remember in High school he started bringing home GQ magazine and his whole looked changed. He started taking risks in outfits. He was the first person I knew to 1) Spend the money on these thick, black, Gucci Frames, and 2) Put a pink tint in them. It was amazing.

    You have to remember, I grew up in Grand Rapids Michigan. It’s a super conservative area. But he didn’t care. He would jam a deep V-neck sweater with jeans and a leather trench. Before the Matrix! What!!! Needless to say a lot of people didn’t get it but I remember how strong he felt and the balls it took for him to do such things. From there on out I was hooked.”


    “This has become one my favorite things to wear. Coming from the northern Midwest layers are the key to staying warm. I love hats, and for men this is one of the few areas we can show individuality without screaming ‘look at me!’



    2. Throwback Gent


    “I started at Old Navy and now am blessed to be in charge of the west coast made-to-measure program for Gucci… It’s a great opportunity for men to fine tune their closets based on their specific needs. It allows them to take control of what they want and how they want pieces to fit without waiting from season to season to see what is offered. I fell in love with this program because of the options available and the freedom it gives myself and the customer.”


    “This is one of my favorite looks. I was able to get my hands on this Vintage Gucci Tuxedo and I try to find any way to piece it with an outfit. The huge lapels and the ultra-low DB button stance is killer… To me it’s a black jacket. I can wear a black jacket with virtually anything.”



    3. Casual Bowtie


    “I used to think that style meant wearing well-tailored suits all the time, but after moving from Chicago to LA it became less and less conducive to the casual life style of Southern California. I realized how much I love to mix and match brands… It’s probably the conservative mentality of my upbringing that has an influence on a lot of my style.

    This is my everyday look. When in doubt, throw on a great blazer. It affords you the ability to be high/low not only in the labels but also in the look. It’s perfect for most any evening out with friends, dates, etc… If you show up to a party or dinner and it’s a more formal affair then unroll the sleeves, put the collar down and take the hat off.”




    Thanks, as always, for reading.

    Yours in style,

    Articles of Style


    Photography by Alex Crawford 

    • Josh

      The blazer in the third look is great, any clue on how to find one similar?

    • Jonathon

      Are you wearing suspenders in look 1&2?

    • http://unseenflirtspoetry.wordpress.com Unseen Flirtations

      Aspiration without desperation, and assured enough to play with ‘the rules’ sans safety net. Yep.

    • Jeanscuffed

      I love high/low style posts especially this one. Where on this site have you featured a guy wearing something from Forever 21? I love all three looks. I’m not a fan of the super wide lapel Gucci blazer, BUT I like how Anthony pulls it off. It’s all about confidence as well, and I can see he wears it better than his clothes. Look #1 is definitely something I would wear.

    • Brent

      The tux jacket looks absurd. First look is pretty cool.

    • Jeff Russell

      While not all the looks are to my taste, Anthony owns every look and just looks comfortable. You can definitely apprecite that.

      • Brent

        It’s a professional photoshoot for a blog feature of course he looks comfortable that is the point. If he looked socially awkward and like he was holding in a bowel movement it wouldn’t be featured.

        • Jeanscuffed

          Cool your jets Brent. He was only complimenting the smooth nature of how the pictures came out. It’s already known if the pictures looked weird or awkward in any way, they would re-do or just not post. C’mon now.

          • Brent

            Cool my jets? That was a very level response?

            • Jeanscuffed

              There’s no pleasing you lol

              • Brent

                The most repetitive comment on this site is always “he looks comfortable” or “not my style but he owns it”

                • Rob

                  That doesn’t surprise me given how many guys I have observed in my day who just look awkward in certain clothes. The site puts up guys who are top level in their style and inspiration. No wonder you see those comments so much.

        • Rob

          You’re right, I totally forgot I was looking at a picture on computer screen! Man, that always gets me every time. I always think it’s real life.

          • Brent

            That is not what my comment is about one bit completely off. But saying a model looks comfortable in every single post is a point that holds no weight since it’s a professional photoshoot that’s meant to make the actor look comfortable.

            • Rob

              I think this is an issue over differing understandings of what a camera shoot can bring. You are correct, it is a professional photo shoot and it is going to turn out looking great no matter what. However, you put me in those same clothes, with the same team and I doubt I am going to “look comfortable.” The photos might turn out beautifully, that does not always entail comfort. I am speaking more about owning the look and making it a natural expression then necessarily poses and expressions on the model’s face. An intangible comfort and confidence that cameras cannot always provide. Though, you may disagree and I think that is fine.

    • Kevin Wood

      I’m so proud of you man so happy your my brother

    • Josh Mendez

      One of my favorite articles. Because I’m only 18, and it started with me back in High School, reading GQ Magazine, competing in my schools fashion show, winning Best Dressed my senior year. I never had the money to spend $500 on a pair of shoes/a nice article of clothing. So I used to just go to Uniqlo, H&M, Zara, & Urban Outfitters and try and mix & match. It’s all about making the item look like it costs more than it really does. I have a Trench Coat my mom got me from Jamaica Ave *New Yorkers (Particularly Queens) know this* and people thought I got it from H&M or Bloomingdales. And my first (and current job) was a sales floor associate at Old Navy. I figured why not get into the retail business if I’m a fan of fashion? So I started in the summer, and 3 months later I became one of the managers. Fast forward to now I’m still one of the managers. But this shows me that what I’m doing is going to aim me in the right direction if I keep at it. Thanks TSB, from one of your younger readers.

    • Koska23

      I’m all for creativity, but the hat in look 3 is a bit much for my taste. I like looks 1 and 2 though. Thanks for the post.

    • amy bennett

      Anthony is my nephew and he has been awesome since he was a baby!!! love you Tony!!!!

    • Miguel

      The first look is on point, the last two kind of busy to my liking, thanks for posting.

    • John B

      I like the post, especially the two first looks. The shoes are amazing (minus the Toms ones) and I really like the DB tuxedo over DB vest (wish I could find one off-the-rack).

    • Ian K

      Wow, that third look is killer! I’m already plotting a way to mimic it with a LA Dodgers cap. Thanks!!

    • Nate

      I love layering and I particularly enjoy the contrasts in color and tonality in the first look. There is enough complexity to keep any men’s fashion aficionado busy, yet the overall look ties together in a decidedly un-fussy manner. My hat’s off (haha) to you, TSB and Anthony for this post.

      • http://www.TSBmen.com/ Dan Trepanier

        Thanks Nate!

    • Dennis

      On the first look, did you mean “Goorin Bros.”?

      • http://www.TSBmen.com/ Dan Trepanier

        Yes. Good catch – just fixed it. Thx

    • http://www.wellbuiltstyle.com/ WellBuiltStyle

      Definitely like the first look. I think it would be that much better without the hat and bow tie. Simple is stylish.

      The other two looks are definitely more “fashion forward” but I find them to be a little too thought out or affected.

    • WideEyesTWBlog

      Not as sure about the other two, but I love the first look. It’s definitely something I would wear, and I really appreciate the inclusion of items I could actually afford. While I still take great and useful inspiration from pieces showcasing mainly high-end goods, it’s nice to take some of the work out of the equation by showing those affordable versions right up front. Nice post.

    • http://whentowear.tumblr.com/ WhenToWear

      I actually like all the outfits, minus the waistcoat in look 2. For some reason is appears more formal than the actual jacket. Other than that I think it hits that perfect medium of looking tailored and looking casual. The layers allow you to go either way when called for.

    • cam

      I guess I would need to live on the West Coast to understand this. Maybe someone else could explain to me a double breasted tux jacket with denim, bow ties with fitted sport caps etc. This is just all over the place.

      • http://www.TSBmen.com/ Dan Trepanier

        Too much structure can kill a man’s creativity.

      • Jimmy_Johansen

        I’m from NYC. I love the 3rd look. I’m not even into bow ties but this is perfect. I would do this in a second. I think I’ve already done a variation of it