Men’s Style Q&A: Sneakers to a wedding? Pocket square tips

This week’s Sports Illustrated style Q&A tackles important questions on how to dress up sneakers, how to choose the right pocket square and how to remain stylish with bigger figure.
Publish date:

This week’s Sports Illustrated style Q&A tackles important questions on how to dress up sneakers, choose the right pocket square and remain stylish with bigger figure. Click here for our first Style Q&A and be sure to check in to the new men's style section of (and download their app) for all your shopping and fashion tip needs.

Image placeholder title

Q: What kind of shoes/sneakers should I wear if I'm going out to dinner with guy friends?  Loafers are too work-related and sneakers usually don't look good with nice jeans, etc.



A: Hey James! A dudes dinner can definitely be daunting: heated fantasy football discussions, a potential credit card roulette loss and, of course, making sure your footwear is on point. Though we can’t help with your draft or luck, we can guarantee that you’ll be crushing the shoe game with a few simple rules. It’s all about your personal style. If you’re a classic man, opt for wingtip oxfords in light brown leather like these. For a more casual/sporty vibe, a pair of textured sneakers like these will work just fine as long as you don’t dual purpose them for the gym. If you’re on the contemporary or trendier side, the reformed lace-up boot is this season’s must have. Pair any of these options with cuffed jeans and a plaid button-down to complete the look and one-up the guys.

Image placeholder title

Q: What's the deal with pocket squares; should they match your tie?



A: Rob, this is one of our most popular questions and the answer is a resounding no. Pocket squares should never match your tie.  Run, don’t walk, from anyone who tells you otherwise. Matchy-matchy is not a good look here and don’t be that guy who tries to make it happen. The key is contrasting while complimenting. Some of our favorite combos are: 1) a black tie with a red, printed square 2) a blue striped tie with a subtle paisley print square and 3) a polka-dot tie with a plain white square. You’re looking dapper already!

Image placeholder title

Q: How should I think about buying clothes (especially tops) when I am handsomely husky?  I struggle with this right now since I want something that fits close, but hides problem areas (e.g. gut).

- Anonymous


A; Hi Handsomely Husky,

We love that! We’ve got some quick tips to help: 1) Wear darker colors. Ever hear that black is slimming? It’s true, and luckily the rule spans across charcoal and navy too! 2) Keep an eye out for slightly longer tees that fit snug at the arms and have a little give towards the midsection. We love this option for your basic tee and they make it in every staple color. For formal button-downs, try Brooks Brothers Regent fit (they’re non-iron too so a definite no-brainer!). 3) Layer your look with a shawl collar cardigan to elongate and slim the torso.     4) Invest in a good tailor to customize suits and blazers for optimal fit, especially around the bicep area. I mean who wouldn’t want tickets to the handsomely husky gun show? 5) Lastly, pair relaxed fit jeans like these with an un-tucked shirt to divert attention away from above the waist. P.S. We’ll all be using this cheat sheet as we pack on the extra holiday lbs!

Image placeholder title

Q: I have a style question on behalf of my husband: Is it ever okay to wear sneakers to a wedding?  If so, what's acceptable?



A: Hi Laura,

Let’s talk sneakers and the major comeback they have had in general–these babies are hot and we’re seeing them worn with just about everything! Your husband sounds like a fashion risk-taker, but when it comes to weddings, he should follow the dress code etiquette to some degree. If it’s black tie, we highly recommend keeping it traditional and not experimenting with sneakers period. If the wedding is a bit more casual, say cocktail attire, we say go for it! Of course make sure your husband wears a pair that’s suave and fashion forward with his suit. Try sneakers in black, blue, or brown. We’ve got faith in your man, he’ll pull it together!