In this post, I recently encouraged tall men to take the plunge and wear skinny or straight jeans. I might have mentioned that I bought my husband a pair for Christmas and much to my delight he liked them (he is not a risk taker when it comes to fashion). Well my delight quickly turned to dismay as I realized he has this image of what to wear with straight jeans and the image doesn’t fit his body type or his style. As a result, he’s only worn them once [insert single tear rolling down my cheek for dramatic effect]. I can’t say I blame him though. I myself have purchased an item a little out of my comfort zone and even though I love it, it sits in my closet because I have no idea how to style it. Isn’t this why we usually stick to the basics in the first place?! Well I love when I’m in that space and come across some guidelines or advice on how to get out of my slump and pull that [insert recent risky purchase here—for me it’s a pair of bright red jeans] out of my closet and go for it!

So here are a few ideas/guidelines. First, you don’t have to dress like a member of a rock band or a 20 year old college kid to rock straight jeans. Now if you love skinnies and you embrace them, you may ignore the following piece of advice. But this will apply to most men:

• Skip the high top sneaker and/or the skin tight t-shirts. Yes, some men rock this look and look good and confident doing it. But these are usually young, very fit, and very metro men who can pull it off. For most of us (or I guess since I’m not a man I should say “you”), it’s not going to feel natural or comfortable.
• *Stick to the basics. Wear a well fitting button up or a V neck sweater. It doesn’t have to be tight but it shouldn’t be very loose or baggy. Try “athletic fit” if you’re average or bigger build, or “slim” or “vintage” fit if you’re thin.
• *If you’re not as thin as you think you need to be to wear this style, try layering. Wear a track jacket, a cardigan sweater, or a blazer over a t-shirt or button up.
• *Nearly any shoe goes- just make sure it’s not too chunky. Since you’re tall, you probably have larger size feet. So you don’t want to wear a super chunky shoe with a skinny leg. Wear a slim shoe.
• *A T-shirt goes with everything. Again, skip the over-sized baggy T. You’re trying to look proportioned. Wear a T-shirt that fits well and if you’re self conscious or have some weight around the middle, go for a casual look with a sweater or sweatshirt over the T. You’ll want to choose a “cool” sweat shirt that looks like you’re trying though–perhaps, a vintage wash, well made, nicely fitting one. Pair that with a nice T (meaning one that you didn’t score for free somewhere ;), cool sneakers and you look casual but still stylish.
• *A polo shirt is a perfect choice. The guidelines are basically the same as for a t-shirt…but a polo is a bit more forgiving than a plain T.

1. Claiborne Button-Down Big & Tall Shirt
2. Classic Fit Button-Front Tall Sweater
3. Classic Fit Cotton Crewneck Tall Sweater
4. Raw Edge Tall Mock Zip
5. Slim Fit Pique Tall Polos
6. Solid Crewneck Tall T

I hope this helps get you in gear to wear skinny (or straight) jeans with confidence! Have questions? Post below!

View more advice here.