Outfit: Simply Stylish

American Eagle Outfitters Men’s Leather Belt ($18). Dockers® Jean Cut Khaki All Seasons Slim-Fit Tech Pants ($36). Old Navy Slim-Fit Built-In Flex Chambray Everyday Shirt ($37).  Nautica Portofino Stainless Steel Watch ($68). Clarks Men’s Bushacre 2 Chukka Boot ($62).

Sometimes the best style is keeping things as simple and classic as possible. A timeless chambray shirt paired with dark british khaki chinos always looks good. Any time on anyone. The details like the jean cut of the chinos and the dark leather belt and boots keep this outfit on the rugged classic end of the style spectrum. A quintessential dive watch is the finishing touch. Simple. Timeless. Classic. Stylish.

Outfits: Fall Monday

Mondays are hard. Even if you love your job, coming back from the weekend can be a hard reentry. I find that putting a little extra effort into my outfit on Monday morning can put an extra spring in my step and make my whole day feel a little easier to handle. So throw on a blazer and some real shoes, even if especially if you are working from home.

Amazon Brand – Goodthreads Men’s Slim-Fit Wool Blazer ($51). Amazon Essentials Men’s Regular-Fit Long-Sleeve Oxford Shirt ($18). The Tie Bar Free Fall Floral Pocket Square ($14). Dockers Men’s Slim Fit Workday Khaki Smart 360 Flex Pants ($40). Gold Toe Men’s Dress Crew Socks ($8). Bruno Marc Men’s Suede Leather Wingtip Boots ($30). Timex Expedition Scout 40 Watch ($41).

Outfits: Attending the Symphony (at Home)

I love attending cultural events. It’s one of the very few activities that I get excited to leave the house for. The Mrs. and I get all dressed up, her in a favorite dress, me usually in a blazer and tie. We often go for dinner or drinks first, parking somewhere that we can walk to both dinner and the venue. We spend an evening enjoying a lovely performance while sitting quietly (but not passively) together. It’s an introvert couple’s dream date.

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Outfits: Sharp Casual Monday

Croft & Barrow® Spread-Collar Dress Shirt ($45 but BOGO). NATO Racing Strap ($5). Signature Gold by GOLDTOE Striped Crew Socks ($10 – 3 pack). Dockers® Slim Fit Original Khaki All Seasons Tech Pants D1 ($40). G.H. Bass & Co. Men’s Parker Oxford Shoe ($39). Casio Anti Reverse Bezel Dive Watch ($48).

A Monday after a weekend full of adventure calls for simple clothes that still look sharp. Roll those sleeves up to your elbows to show you’re ready to work. Only you will know that your pants are as comfy as sweatpants. Keep an eye on the days’ important milestones (lunchtime and quitting time!) with your dive watch styled on a summer-worthy NATO. Striped socks and saddle shoes keep things firmly on the casual side of sharp casual.